"I don't want an explanation. I just want to be left out of your campaign. I can't paste on a smile and pretend you're man of the year. "
|Miles Hollingsworth III|
|Full Name||Miles Hollingsworth III|
|Nickname(s)|| Ballingsworth (by Dallas)|
Mr. Silent (by Maya)
Richy Richers (by Grace)
Money Bags (by Grace and Zig)
Sherlock (by Dallas)
Rich Boy (by Zig)
Hollingsworth (by Zig)
Young Money (by Zig)
Weirdo (by Damon)
Hot Wheels (by Zoe)
Little Boy Blue (by Zoë)
Money Bag Miles (by Grace)
Bud (by His Dad)
Dork (by Zig)
|Date of Birth||1998|
|Family|| Frankie Hollingsworth (Sister)|
Hunter Hollingsworth (Brother)
Miles Hollingsworth II (Father)
Mrs. Hollingsworth (Mother)
|Relationships|| Tristan Milligan (Boyfriend)|
Maya Matlin (Ex-Girlfriend)
Zoë Rivas (Ex-Girlfriend)
Many Previous Unnamed Relationships/Flings
|School(s)|| Degrassi Community School |
Unnamed Boarding School (Expelled)
|First Episode||Summertime (1) (1301)|
|Portrayed By||Eric Osborne|
Miles Hollingsworth III is a Sophomore (Grade 10) at Degrassi Community School. He's preternaturally good-looking and appears to be nothing more than a typical rich bad boy, but looks can be deceiving. Miles is just a teenager looking for love and acceptance, especially from his father, Mr. Hollingsworth II, after being kicked out of boarding school. His father is a popular businessman running for mayor, but won't let his reckless son get in the way. He often verbally abuses Miles who, in turn, acts out in rebellious ways as a result. By the end of season 13, Miles appears to be bisexual.
He has been long time best friends with Winston Chu, whom he calls "Chewy", and good friends with Mike Dallas. He's also close with Tristan Milligan whom he started a relationship with after sharing a kiss together in "Thunderstruck." He was also a good friend of Maya Matlin and developed a crush on her before the two started a relationship, later breaking up. He has a younger sister and brother, a set of twins, named Frankie and Hunter. He is now on good terms with Zoe Rivas. He was rivals with Zig Novak and seemed to have a dislike towards Drew Torres, however, it appears they are now on good terms. He is labelled as "Billionaire Bad Boy." He is portrayed by Eric Osborne.
Season 13In Summertime, he is seen at Degrassi watching Maya bump into a display board and smiles. Later, he watches Maya do a pizza delivery scam to try to get into a club, but tells Maya while the scam was a good try, it won't work. She argues that it might and he tells her, once again, that it won't. He also ends up offering Maya a hit of his joint, which she refuses. Maya and Miles introduce themselves, and he gets her to come see the concert backstage with Zoë and Tristan by telling Maya that he's with the band.
There is an incident backstage where Maya tells Tristan that Zoë's character on West Drive is getting killed off. Zoë then steps on Maya's foot, causing her to trip and spill her water bottle on the band's equipment's, therefore ruining it, halting the concert. A security guard comes and asks them whats going on and Maya tells him that Miles is with the band. The security guard reveals that Miles actually isn't with the band and leads Zoë, Tristan, Miles, and Maya away. Tristan insists how he doesn't want to go to jail.
Miles' dad shows up and tells his son to come with him and for everybody else to simply go home. As Miles passes by Tristan and Maya, he overhears them discussing how they don't have any money to get home. He stops and hands Maya his credit card and tells her the PIN number and watches as the two walk away. At Miles's house, he is seen stealing liquor away from a table. He introduces Maya to his buddy Winston, whom he calls Chewy.
After drinking some liquor, Maya drops the bottle which leads to Miles being viciously scolded by his father. Miles' says I hate you as his dad opens the door, with Maya asking if he is okay, but Miles' say this is normal. In retaliation, Miles flips and jump in the swimming pool even after Maya tells him not to do anything stupid. Winston jokes that Maya has to "go fish him out". However, Maya responds by saying, "No. I can't be here. I can't be around guys like him," and runs off. From inside the pool, Miles can be seen watching her as she hurries away from the scene.
At the end of the episode, while Maya and Tristan are on the bus, the trip instructor announces that they have two last minute additions to their trip. Miles and Winston then climb aboard on the bus much to the two's shock. Miles walks behind Winston as he takes his seat, cupping Maya's shoulder as he passes. As he and Winston take their seats, Maya asks him how he got on the trip last minute. Miles explains that his dad wanted to send him off for a bit and tells her that they are "going to spend the summer together after all". However, Maya tells him that she's there to spend it with her best friend, not him, therefore rejecting him. He remarks, "Your loss" as he glances away. Zoë shows a clear interest in him, warning Maya to keep her distance from him.
In All I Wanna Do, Miles is seen getting out of a car in France with Winston and teases him about whether or not he can land a French girl. He is rooming with Winston and Tristan, who absentmindedly checks out Miles while he gets dressed. Miles and Winston tease Tristan for staring, and Tristan then claims that he is straight and has a girlfriend. The two don't believe him, but Maya then enters the room and Tristan hurriedly tells them that Maya is his girlfriend, who catches on and plays along.
Later on, Miles and Winston are seen hanging out together and convince Tristan to go and hang out with Maya. He does so and to up the ante, Miles suggests that two kiss. Maya kisses Tristan, who is disgusted, and Miles and Winston laugh.That same day, Miles returns to the dorm room to find that Tristan has put a sheet around his bed so that the boys will not feel uncomfortable being in the same room with him. Miles assures him that he and Winston don't care and that they're just joking, but Tristan calls what they're doing as bullying much to Mile's surprise.
When Tristan returns later, Miles has taken the sheet down and put a candy on his pillow. He asks if it's a prank, but Miles walks in and tells him that he and Winston weren't teasing him for being gay; they were teasing him for acting straight when they already knew he was gay. He also explains that neither him nor Winston is homophobic and is offended that Tristan would make that assumption. Tristan is relieved and says that he could hug him right then, but Miles takes his shirt off so that he can go shower, and Tristan becomes distracted and says that they can't now. Miles pulls him in for a hug anyway, and tells him that he's going to have a great summer. He then exits the room, leaving a smiling Tristan alone. It is obvious that Tristan has developed a crush on Miles.In My Own Worst Enemy, Miles walks into class with Tristan and is seen to be teaching him french. He then goes to sit elsewhere, and Tristan tells Maya that Miles bought him food. Tristan also confesses that he believes Miles to be gay, and Zoë reveals that she too is after him and that he's straight. Madame enters and tells the students that she wants everyone to buy French food for the rest of the class to sample and that they should be in groups of two people. Miles agrees to be partners with Tristan, which angers Zoë.
Later on, Tristan and Miles go to a restaurant where Miles orders food for him. Tristan tries to get Miles to comment on the cashier, but he just claims that she isn't his type. A song begins to play and Tristan says that he loves the song, to which Miles embarrassingly admits he did a dance to once. He then tells Tristan that he took a hip hop class as a young boy when his sister was in tap dancing lessons next door, although his father pulled him out soon after finding out. Tristan apologizes on his behalf and Miles shrugs and claims that they just don't see eye to eye, but thanks Tristan for being a good friend.
Tristan then kisses Miles, who appears to be clearly shocked. He is embarrassed, but Miles tells him that it's not a big deal and to forget about it. That night, Tristan tells Maya that he thinks that Miles liked the kiss and is considering asking him out. Right then, the two discover Zoë in Miles' lap on the couch stroking his hair, leaving Tristan disappointed and upset causing him to quickly leave the scene. Maya watches the new couple a moment longer.In About a Girl, Miles first appears in a classroom making out with Zoë and then takes his seat for class. He is then seen making out with Zoë again below the balcony, much to Maya's annoyance. Maya and Tristan form a plan to stop Miles and Zoë from their constant PDA. The plan goes wrong when Maya dumps water on the teacher instead of Miles and Zoë and they both get detention for it. Miles and Zoë are seen looking up at the balcony and laughing at Maya and Tristan.
He later appears when Maya is scrubbing the floors in detention. He confronts her about the water incident and she says he's done worse things and that she is just annoyed with him and Zoë always making out in public. Miles says that Zoë isn't his girlfriend, leading Maya to ask if he just makes out with random girls. Miles tells Maya if they ask nicely and then asks her if she wants to kiss him. Maya answers that she "wouldn't kiss him with her dog's lips". He then says that he believes she tried to pour the water on him and Zoë because she likes him, but Maya instead insists that Tristan likes him, not her, and only did it for him.
Maya reminds him of the the kiss he and Tristan shared and how humiliated he feels to where he can't show up for class because of his constant behavior with Zoë. Miles looks over Maya's shoulder just in time to see Tristan standing there and listening to their conversation. When Tristan leaves, humiliated, Miles asks Maya, "Are you sure you don't want to kiss me?" Maya just looks at him and leaves to follow after Tristan.In Cannonball, Miles and Winston are seen getting dressed before Maya walks in, trying to find Tristan. Miles says that Tristan already left before they woke up. As Maya is leaving, he says that she should take someone with her to stay safe. She agrees with him, and walks over and takes Winston and drags him off to the doorway. Winston asks why not take Miles, who is familiar and been in Paris before, Maya turns and looks directly at Miles. She says she doesn't need "a guy like him" around. Miles throws Winston his shirt without a word, and as they leave, he looks downward, clearly upset.
Later, when Winston convinces Maya that she needs Miles to find Tristan because he speaks French and knows his way around Paris, they walk in to see Miles and Zoë sitting on his bed. Miles, at Zoë's suggestion, makes Maya get on her knees to ask him for help. When she does, she is required to ask him again, but this time in French. Just as she begins speaking in French, he cuts her off and seems to push Zoë aside carelessly, eager to help Maya.It is raining outside when they go to find Tristan in the evening, and he is carrying a black umbrella. He stops by a fast food place, making Maya upset, and offers her a fry. When Maya looks like she is about to cry and says she doesn't know what to say to Tristan even if they find him because she is a terrible friend, Miles assures her that it'll be fine and all she has to do is talk to Tristan. When she remarks if she is supposed to hope, "the wind will carry her words to his ears."Miles suggets to walk across the street to where Tristan is. He gives her the umbrella and leaves.
In class, Maya and Tristan are doing a presentation on the pillory as a form of public humiliation, and Maya suggests Miles try it out, joking that he "fits the bill" for it. Tristan jokingly asks if anyone has any rotten fruit to throw at Miles. When the bell rings, Maya and Tristan almost leave Miles stuck in the pillory. When Miles calls to be let out, Maya stays back and asks quietly why he was so nice to her the other day. Miles says she must have caught him on a good day. They stare at each other for a moment before Zoë interrupts, reminding Miles that he promised to take her out to a fancy restaurant. Miles seems slightly reluctant. Maya lets him out of the pillory, but before he leaves the classroom following Zoë, Miles tells Maya he'll see her around with a smile. He can be seen taking a quick glance at her from behind as he leaves the room.In Honey, he is seen in class when Madame Criquet tells everyone not to wear vulgar or typical teenage Canadian clothing to a fancy French restaurant, but fancy clothing. After Zoë makes fun of Maya for wearing Converse, she tells Miles that he looks hot "like that". He asks "Like what?" which Zoë then says she doesn't know and kisses him.
At the dinner, he sees Maya in her dress and is obviously impressed by how she looks, not even able to form a sentence, clearly finding it flattering on her. Zoë sees this, and throws her drink on Maya as she sits down. Miles looks at Zoë angrily as Maya and Tristan leave to clean up her dress. Later, he informs Maya and Tristan that he ended his relationship with her because of how she acted towards Maya. He also warns her to "watch her back" and when Maya asks why, he tells her that Zoë has this "crazy idea" that he's into her.In This Is How We Do It, he can be seen walking with Winston who is trying to get the attention of a few girls, who don't even know him. He remarks how Winston has been there for a year and not even one girl knows him. Winston says that none of the school girls were worth knowing just as Miles notices Maya and Tristan. As he looks at Maya, he says there might "one or two worth checking out".
Later on, he walks into class and again notices Maya and Tristan. He asks Maya that since he's new to Degrassi if she has "any good girlfriend recommendations". Maya sarcastically says she'd never stick him with "some poor, unsuspecting girl", causing him to say, "You mean some very lucky girl" as he sits down next to her. When Tristan brings up his fling with Zoë, Miles admits that dating Zoë was a mistake and that it was all behind him now. Tristan, who notices Zoë behind them, remarks, "literally". Miles looks up and behind me to see Zoe. He asks her if she's attending Degrassi now and is clearly disdained, dropping his head and obvious annoyance. As Mr. Perino walks in, he and Maya and Tristan take their seats.
As Zoe tries to leavea and Mr. Perino says she can't, he and everyone else watch Zoë lash out on Mr. Perino in shock and surprise. Later, Miles, Maya, and Tristan are seen talking to each other in the hallway about the basketball team until Zoë interrupts them and mentions that she's interested in joining the power squad. Miles tells her off instead and walks off with Tristan and a reluctant Maya.
In You Got Me, he is seen alongside Tristan and Maya buying tickets for the Beach Bash and running into Frankie, his sister, and Zoë. When Zoë tries to "jerk tax" him as he pays for the tickets, he teasingly remarks to Zoë that she's still "carrying that torch for him". When Zoë says since she "dumped" him that she's found her friends, causing Miles to remark how he thought Frankie had better taste in friends. Zoë then says that she is with Drew Torres, although Maya and Tristan bring up how he already has a fiance who is away at university.
Later on, Miles is seen arriving at the dance behind Maya and Tristan. When Winston tries to dance, Miles says that is the exact reason as to why he doesn't have a girlfriend. Later, he is seen flirting with Maya for the remainder of his time there. Zoë eventually becomes jealous and drags Drew in front of them to dance. When Drew begins acting strange, Miles make a joke out of it. When Zoë remarks why not he and Maya have sex before she runs off, he and Maya laugh.He is seen in You Oughta Know trying out for the basketball team alongside Tristan. He is desperate to land starter position on the team, as it is what his father wants, despite it being highly unlikely since he is a sophomore and is going up against juniors and seniors. Tristan tries to make conversation with him, wanting to have a, "guy best friend," instead of his usual female crowd, and Miles invites him over to his house since he is having a party.
During the party, he is talking with Winston and Tristan when they are notified via their cell phones of the official listing for the basketball team. Despite having made the team, Miles is upset that he didn't get the position he wanted and storms off. Tristan follows after him, concerned, and Miles says how his father is going to be pissed that he failed to get starter position.
Tristan asks if he'll just simply be happy that he made the team at all, but Miles answers that's "not really his style" and that his dad is "much better at disappointment". He then says that he just needs something to give him "an edge". Tristan says that he hopes he's talking about a personal trainer. However, Miles tells him that the other guys at his old school did it and that it isn't a big deal. Tristan, though, is visibly surprised and says that steriods are a very big deal.
At the end of the episode, Miles is seen getting ready for his first basketball practice just as Tristan comes up to him with a small plastic bag of pills, seemingly steriods. He claims to have gotten them from his older brother and Miles happily hugs him. He tells him that he gave him just what he needs to make starter. Tristan appears nervous and sit down and Miles asks if he's coming since he doesn't want to be late for his practice. Tristan says he'll be out in a minute and Miles leaves.In Everything You've Done Wrong, Miles has officially made starter position. Tristan is happy for him until Miles requests more steroids, believing they are what he needs in order to keep his position on the team. He also tells him how he has spread the word onto the team that he is getting steroids from someone much to Tristan's anger, who says that he can't be "giving away drugs like candy". Miles assures him that he didn't reveal his name and that if he gives him the drugs, then he will do the distributing personally himself. Unknown to Miles, Tristan didn't give him real steroids, only vitamin D tablets.
Later, Tristan has decided to come clean to Miles and comes up to him while Miles is at his locker. Before he can say anything, Miles tells him that the "steroids" have already been given to the whole time. Tristan then confesses to him that the drugs are fake since he was worried and didn't want him doing real drugs.
Miles quickly becomes angry at Tristan and says that he doesn't need him to worry about him and that because of him, the whole team is going to think he's stupid "just like his dad". He slams his fist into the locker and begins walking off as Tristan insists that he is willing to come clean so he won't suffer any trouble. Instead, Miles asks Tristan how he is able to lie to him because he "thought they were friends" before storming off.
Miles is next seen in the boy's locker room changing as Tristan goes up the boys who are taking his "steroids". Miles watches as Tristan reveals himself as the "supplier" and how he has learned of the many random drug tests that will be given to them. He offers a dosage of pills that will wipe the evidence of the "steroids" clean from their systems before declaring that after this, he is done with "supplying" and is "out of the business."
As the team leaves, Miles asks him what he actually gave them and he answers that he gave them b12 tablets and when they test clean they will think it was another pill doing the job. Tristan again apologizes for what he did, but Miles says that he understands what he did and that he was so determined to make starter position that he was "messed up" for a bit. He also says that he appreciates Tristan looking out for him and that there's an "up side" to everything that he's now realized... he made starter position on his own.In Who Do You Think You Are, Miles can be seen watching Maya as she performs her song project in front of the class, happily smiling, and joining in when the class applauds for her. Afterwards, Maya asks him for his opinion of her song. He responds that he was thought it was "okay", causing Maya to smile in amusement before she begins to walk away. However, Miles stops her, implying that he has something to ask her. He then asks Maya out, pulling out two tickets, inviting her to attend a concert with him the following day. Maya is clearly hesitant, and asks if she could get back to him. Miles is visibly disappointed, but says sure before leaving Maya with her thoughts. He is next seen watching Maya's new music video alongside Maya, Tristan and Zoë. He can be seen getting worked up and jealous as he watches Maya's romantic and intimate scenes with her male music video co-star. As Maya is ecstatic over the video, believing it will get her noticed as a musician, she notices Miles's tense and silent expression and asks him for his opinion about it. He responds, "It's fine... if you're into porn". He then gets up and abruptly leave in a huff.
Later on, Maya meets up with him in the hallway and asks if he's mad at her. Miles asks why he'd be mad at her. Maya brings up the guy in her video and he says it's not like she's his girlfriend. Maya then mentions the concert and begins to apologize for declining when he says that he figured she just wasn't ready for a relationship yet when she just wasn't ready for him. Maya insists that isn't the reason at all and he says it's fine since he'll just find someone else to go with him and admits that he's really just surprised; she isn't the person he thought she was. Maya becomes confused and asks if it's about what she did in the video. She insists that was only acting, not the real her, and that she was doing if for the sake of her music career, causing Miles to retort, "So you were a slut to get attention". This comment makes Maya freeze in shock and Miles tells her to check out her Facerange fan page as it's what everyone is saying about her. He walks away from a stunned and confused Maya.
In class later, Miles sits as far away from Maya as possible. He watches at Maya is bullied by fellow classmates for her video and is openly slut shamed in front of the class when she tries to give a report on Jane Eyre. When Maya finally breaks down and flees from the classroom in clear distress, Miles looks downward in obvious remorse, clearly feeling regret.
In Barely Breathing, Miles walks into the music room as a male student begins forcing himself onto Maya, who tries pushing him away. Miles yanks him off of her and punches him before literally throwing him out of the room. Maya, in shock, asks him if his hand is okay. Miles says that it isn't, but that it was worth it. When Maya says how everyone believe that she is a slut, Miles tells her that they're wrong and admits that he was wrong to have said what he did about her. He asks how many guys she's kissed. She answers three. Miles reveals how he's kissed fifty different girls and that someone should make a page about him. Maya remarks how since he's a guy people would "probably build him a statue". When Maya says how all she wants if for it to just go away, Miles says that he might have a solution and offers her his hand. Maya looks at him for a moment before accepting it.
Miles and Maya meet up with an older punk girl who recognizes Maya from her music video. It turns out that Miles has payed her to find out who created the page that resulted in Maya's bullying. The girl explains how she knows the creator of the page used a fake account, but that she managed to crack them into unknowingly giving their identity up before showing her who started her page. Maya is shocked to see that it is Zoë, leading her to get into a cat fight with her and landing the two with a meeting with their mothers' and the principal.
After Zoë gets off scott free for the page, Maya storms into the music room as Miles sits on the table, playing the electric guitar. He guesses that the meeting didn't go well. Maya rants to him about how Zoë isn't being punished for what she did and that her mom doesn't want to press charges because she was "sorry". To cheer her up, Miles begins playing the guitar and singing a playful song, bringing Maya to laugh and join in with him, singing a duet together. Miles jokes that she should "enlighten" everyone about the true person Zoë is. In class, Maya volunteers to sing a song in class. Miles attempts to stop her, saying how he was only joking, but Maya says that she is very serious about it. When Maya leaves the classroom when being sent to the office for her song, Miles looks down once again guilty. As a result of "threatening" Zoë's life, Maya is faced with suspension.
That night, feeling guilty, Miles sneaks over to Maya's house window as she plays her cello and taps on the window to get her attention. Maya stops and opens it to ask what he was doing there. He admits how he feels like he pushed her into doing the song, but Maya says that Zoë had it coming. He says that Zoë is jealous of her because of she's "talented, funny and awesome" in ways that Zoë will never be. Maya says that he doesn't have to say things just to make her feel better. Miles, however, tells her, "I'm not... trust me". They share a clear moment before he leans in and kisses her. As he leans back, he says how school is going to suck without her. Maya smiles before hearing her mother about to come into the room. Maya quickly urges Miles out the window before saying a quick, "Wait! No." She gives him one last quick kiss before he descends out the window.In Black Or White, he is seen with Maya and Tristan in Maya's living room on the couch beside her with his arm around her. He laughs with her as Tristan's performs his play script and makes suggestions for him as how to land a more serious role in his drama and acting class.
In Spiderwebs, it is mentioned by Maya that Miles is away for Thanksgiving.In The World I Know, Miles is with Tristan and they sit next on either side of Maya during lunch. They ask her if she wants to go out for lunch to a popular restaurant that Miles named to be good. However, Maya says she can't go since she has work to do for Remedial class. Miles asks if they give a serious amount of work as he takes a peek at her assignment. Maya says it wouldn't be that bad if she wasn't partnered with Zig Novak. Recognizing his name, Tristan is shocked and he and Maya get into a discussion about him as Miles looks at them in confusion. He asks them who Zig is. Maya insists, "Nobody" as Tristan claims, "Her ex". Miles retorts how those are different things.
Maya explains that Zig isn't her ex since they never dated, but Miles stares at her for a moment. Maya then goes on to say that her relationship with Zig is complicated since they had kissed, earning a surprised chuckle from Miles, but that they haven't talked since last year. Miles insists to her that he isn't going to get jealous "over some Rubber Room skid". Maya looks down awkwardly before Miles then abruptly asks, "Wait, I'm prettier, right?" His comment makes Maya laugh before she says "Of course" and gives him a kiss.
However, Tristan says that Zig, despite his new behavior, is still clearly in love with her. Maya blows off his comment, insisting that he's been watching "too many teen soaps" lately. She urges them to leave while she finishes her work. Miles and Maya share another quick kiss before he leaves with Tristan.In Better Man, Miles walks in on Tristan giving Maya a dark make-over and asks if he missed "make over Monday". Tristan says no, just Maya paying Grace for a list of "Rubber Room Do's and Don'ts". Miles then takes Maya's phone and reads the list of things to do and not to do when you're in the Rubber Room, to which he laughs at. He asks Maya if she really thinks she can do all of this, to which she says she has to if she is going to survive the Rubber Room. Miles asks why she should even care if it's twice a day. Maya says that it doesn't matter since being in a room full of people who hate you is the worst. Tristan the asks her to not "turn into that weirdo in the back of the class". Maya then looks at her reflection in her phone and Miles remarks while rubbing her head that she'd "make a cute weirdo".
Later on, he runs into Maya (who is wearing more darker and edgy clothes to fit in with the Rubber Room kids) as she's making her way out of the school and reminds her how she's supposed to go into the school in the mornings, not out. Maya then gestures and points to a group of the Rubber Room kids behind him. Miles looks back and turns to her, stating that she is planning to skip school to hang out with them, clearly disapproving. Maya begins apologizing, insisting that now she is starting to finally fit in with them.
Despite still not approving, Miles relents saying that she does make a cute weirdo, making her smile. He gives her a kiss and walks into the school.In Dig Me Out, Miles is at his house, throwing a pool party. He is seen flirting with Maya before noticing Drew and Zoe arriving. As he approaches them, he retorts how he didn't expect Zoe to arrive there and with "a narc", referencing to Drew. After Miles tries to get them to leave, Drew threatens to reveal the party and how he is distributing alcohol to minors to his father if he doesn't allow him and Zoe to stay. This threat silences Miles, who stares at Drew. Maya comments on Drew's method of blackmail and remarks that he and Zoe are made for each other. Miles walks off as Maya follows behind him. Later, he challenges Drew and Zoe to a game of chicken pool fighting, but is declined.
In No Surprises, Miles is with Maya at his house and in his pool. He tells her to get in or prepare to get splashed. When she tells him she doesn't have a suit, he takes off his swim shorts and tosses them at her and tempts her into skinny dipping. Maya hesitantly decides to go through with it, telling him to turn around. He does so as Maya begins taking off her clothes and jumps into the pool.
After jumping in the pool, they stare at each other for a moment, smiling, before overhearing his father and his campaign staff about to come in. Maya freaks and rushes out as he tries telling her it won't be a big deal since he is in a good place with his father. His dad and campaign staff then come in and stare at a towel covered Maya who awkwardly greets them. Maya tells Mr. Hollingsworth they were doing homework as Miles asks if she can stay for dinner. His father says it would be best if she left and she agrees, leaving in a towel and taking her stuff. Miles is scolded by his father for being embarrassing him in front of his staff. He yells at him to not humiliate him again and to get out of the pool. Miles asks if he could toss him his shorts. His father throws his shorts at him, smacking him in the face, as Miles is left staring downward.
During breakfast with his family, Mr. Hollingsworth gives Miles the silent treatment over the incident. Mr. Hollingsworth praises Miles' siblings Frankie and Hunter for their work on his campaign and suggests Miles follow their example. He tries insisting he was doing good since he hasn't gotten into any trouble since the school year began, but it still isn't good enough. After his father has left, Miles complains to his mother about the way his father has been treating him and she suggests he try harder.
Later on, in class, Maya asks him if she left a bad impression on his father. He tells how how he already told her not to worry about it, but she insists that she is. He tells her that he got blamed for the entire situation and that everything is usually his fault. She says that she has suffered her fair share of parental drama and that sometimes you need to go the extra mile in order to make your parents happy. He mentions his father's campaign she she urges him to help out with that. She then teases him, making him believe she is going to kiss him, only to turn away at the last second, smirking. He smiles to himself in amusement.
At the Hollingsworth house, Miles, Maya and Winston begin helping Mr. Hollingsworth with his Mayoral campaign. Miles is excited to show his dad all the work he has put into helping out and goes outside to show him. However, he instead sees his father flirting with his campaign manager. He stares at them for a moment before looking away in plain disgust. At school, the next day Miles show Maya a necklace that he intends to give to Andrea, his fathers campaign manager, by slipping into her bag and see how she reacts to it and find out what is really going on between the two. Maya is reluctant for him to go through with the plan, warning him how it could just be one big misunderstanding. He still decides to go through with it to see what is truly going on.
At his house during the mock press meeting, Miles sees Andrea happily smile as she opens the fake gift and reads the card he wrote. With his suspicions confirmed, Miles is left furious. During the media training meeting, Miles fails to impress his father with his new attitude, mocking him with saying sarcastically how he hopes to be just like him and leaves abruptly, kicking his chair over before storming out. Miles' mother follows him out, demanding to know what is going on with him. Miles tells her that his father is having an affair.
She says that she knows about it. Stunned, Miles asks her why she won't leave him or even try to deal with the matter. She refuses to discuss her marriage with him and that they will deal with it after the election. Now clearly disgusted, Miles remarks how the election always comes first before anything else and leaves.
That night, Miles is with Maya laying on the couch together. Miles talks to her about how he felt so angered at his father and how feels about the whole situation. Maya asks him if he is okay and he declares that he is done with his parents and their political plans. Miles then says how he has her now. After a moment, he tells her that he loves her. Maya looks up at him in clear surprise and says that she loves him too. He kisses her on her forehead and she lays back down on his chest, smiling to herself. The episode ends as Miles looks upward in deep thought.
In Basket Case, Miles is first seen on the phone with Maya, talking about his parent's going away for a little while. Maya asks if that means he has the place all to himself. After confirming it and asking if she wants to come over, Maya teases him about getting the chance to maybe see "how that skinny dip ends". This leaves Miles slightly nervous. His father then walks in alongside Drew, bringing Miles to end the call, and ask why he was there. Drew reveals how he has been assigned as his personal baby-sitter, infuriating Miles, as his father tells him how there are going to be no girls allowed and no wild parties.Miles, while at school, complains to Winston about how Drew has followed him everywhere he's gone to, including waiting by his locker, outside when he used the bathroom, etc. He says how he is just trying to score points with his father is all the more furious about his father actually assigning him a baby-sitter, not trusting him to spend the night alone in his own house, and is sick of him trying to control his life. He then declares that if he is believed to still be required a baby-sitter, then he will act like he still does then. Winston then asks if that means they are going to be throwing a party. Miles says they are going to be throwing the party. Winston warns him how his father will be furious upon finding out and Miles says his dad is cheating on his mother, so he doesn't care what he thinks. Winston then begins to send messages out, but Miles says they need to take care of Drew first. After a moment, he smiles.
In the hallway, he comes up to Drew who says he needs to take him home AY-SAP. Miles head gestures to Winston nearby in the computer room, who sends Drew a text message disguised as a message from Mr. Hollingsworth. Drew reads the message, believing that Mr. Hollingsworth needs him to do a bunch of campaign work that will last hours. Miles said he'd help out, but he needs to go straight home to finish an English essay. Drew almost begs him to not get into any trouble and Miles assures him he will behave. Drew then leaves as Winston comes up to him, realizing he bought it. Miles asks who is on the guest list and Winston confirms he invited everyone. Miles, looking at him, says he just ditched Drew. Winston says he had faith in him. Zoe then passes and thanks him for the invite and she'll see him later. Miles asks why he'd invite Zoe when he knew she was trouble. Winston responds, "Isn't that the point?" Miles then goes with the choice then declares how this party is going to be epic.
Once the party's gotten started, Miles is thrilled with the large amount of people that showed up. Miles watches with Winston Zoe drunkenly yelling for who's ready to have some fun tonight as the crowd cheers. Later, Maya shows up, who isn't at all happy with the party. Miles drunkenly kisses her, and Maya pulls back asking what's happened to their original plans. Miles, clearly drunk, says how his dad told him he couldn't have anyone over. Maya, looking around stunned, says "So you decided to invite the entire school over?" Miles tells her that they'll have some alone time together. Maya says she isn't worried about that, she wants to know what he plans on doing; throw a huge party and get caught by his father to make him angry. Miles tells her, "Pretty much". Maya sarcastically remarks, "Awesome".
Miles tries encouraging her to let loose and have some fun, saying how he thought she'd enjoy it, but Maya refuses to. She tries urging him to sober up, but Miles accuses her of becoming judgmental. Maya says how she understands that he's going through something rough, but asks him to call the party off before his whole gets trashed. Miles then yells at her, saying how she doesn't get anything. Maya, staring at him, calmly tells him "Goodnight, Miles" before walking off as Miles asks if she's really just leaving.
That night, Miles is approached by a drunken Zoe who asks him where his "apple cheeked girlfriend" is at. Miles tells her how she didn't enjoy the party. Zoe asks if they had a fight and Miles says that she just doesn't get him. Zoe remarks how "judgy people like her" with their "perfect little lives" have no idea what it's like to be someone with real problems. She says that once people like that make up their minds about them, they don't change. She then strips down to her bra and panties, and collapses on top of him, wrapping her arms around them. She says that whatever people like them do together, it doesn't matter. Miles says to "Let them think what they wanna think". Zoe then leans in, inches from kissing Miles.However, Winston then pops up, snapping a picture of the two together. Miles, leaning up, asks what he's doing. Winston says he's preventing him from making a huge mistake. Miles says it's none of his business. Winston reminds him about his girlfriend who is "awesome in every way possible" and asks why he would want to screw that up. Miles says she was the one who took off and if he's supposed to run after her or something. Winston answers with a solid, "Yes!" because "that's what you do when you screw up". Miles then appears to come to his senses and climbs away from a passed out Zoe. After dusting himself off, he yanks out some flowers from a nearby pot. He sees Zoe and, after some contemplation, tells Winston he can't leave her out there and to put her in the pool house or something. Winston says he can't lift Zoe by himself and they lift her up together. Winston then snaps a picture of them together to use as leverage in the future on her. The two then carry her off.
Miles then tries to make his way out of the house and runs into Drew, who found out about the party and demands to know what is going on. Miles, still a bit drunk, says how it's a party and to have fun. However, Drew firmly says he is not going to leave him with this mess to clean up himself and threatens to call his father. Miles, though, says that means they're both getting into trouble since it was his job to make sure this never happened in the first place. He tells him to move, but Drew then reveals how his father came up with the "Miles Management Plan" and says how his father came up with several options on what to do in case he screwed up his campaign election again. Miles, despite being stunned, shoves him and storms out.
Later on, Miles arrives at Maya's house and knocks on her window, getting her attention. Maya, annoyed, gets up and opens it. She asks him why he is there and he says he came to apologize. He admits he was wrong and should have never thrown the party in the first place and stopped it when she asked. She asks him if he even cares about her. Miles tells her that he wouldn't be there if he didn't. He tries to insist that she's the only thing he cares about. Maya says he clearly cares about his father otherwise he wouldn't be putting so much energy into making him mad. Miles admist to her how he just wishes his father would stop treating him like crap. Maya simply tells him to not give his father a reason to then. She then shuts the window, closes the curtain and walks away. Miles tries to call out to her, but she ignores him.
Miles explains how he threw the party because he was mad. His father asks if it was because he hired Drew as a sitter and Miles tells him that he knows about the affair. Stunned, his father is silenced. Miles goes on to explain how while mom may be okay with it - he isn't. His father, now calm, tries explaining it was complicated. But Miles says how he doesn't want an explanation, he just can't go along with his image of being a perfect son and smiling as though he's "man of the year". Relenting, his father says okay, but not to pull any more stunts like last night again. Miles promises him he won't. His dad says he will call a service to clean up, but Miles says it isn't need; it's his mess, he'll clean it up. His dad looks at him, clearly for once, approving of him. He walks off as Miles looks on.
The following morning, Miles is cleaning up the house from the party. Frankie asks if Maya accepted his apology, and he says that she didn't. They hear a car door close and Miles realizes their parents are home. His dad then walks in and sees the mess, and asks where Drew is since he had been assures nothing would happen. Miles tells him how Drew had nothing to do with the party and was the one who ended it. He asks Frankie if he is telling the truth and she confirms that Drew stayed on top of things. He tells her to go get ready for school and she leaves.
In Unbelievable, Miles tries to win Maya over again when he runs into her at school. He tells her how he made up with his dad, but Maya retorts if he wants a medal. He says how she can't still be mad at him for the party, but Winston remarks how she clearly still is. Miles reminds her of how he already apologized to her, but Maya tells him that it was not accepted. He then puts a expensive gift on her desk and asks, "How about now?" Maya is stunned and says that he can not expect to buy her forgiveness. Miles says that he won't be able to focus on his basketball game with her mad at him. Maya, shocked, remarks, "Are you serious?" before taking her things and getting up. She picks up his gift, puts it back on his desk, and walks away from him. Miles mutters a "Come on", looking exasperated.
During his basketball practice, Miles is distracted by Maya not willing to forgive him so easily. Dallas bounces the basketball on his back and notes how he's clearly distracted. The other boys ask him what's up and he explains how Maya is still mad at him for throwing the party. They ask if he apologized to her and whether he got her a gift. He says that he did all of that, but she won't budge. Tristan explains how he needs to make a grand gesture and something public that will send his message of a sincere apology to her. Miles says how that seems like it will be a lot of work. Tristan says there are five of them and that they can all pitch in to brain storm ideas together. Dallas accepts the idea for a few minutes and Miles is willing to do it as long as it means winning Maya back over.
Later on during class, he is rummaging through a chest of school costumes when Zoe closes it and demands to know they had sex at his party. He shushes her and pulls her downward. He says that Maya cannot hear about this. Zoe says how the last thing she remembers is them talking and then waking up naked in his pool house. He tells her how she tried kissing him, passed out and he and Winston put her in the pool house to sober up; nothing else. Zoe is relieved, commenting how gross it would have been if they did and walks off. Miles then resumes going through the chest.
During the Sing Off, Miles has Winston trick Maya into arriving by telling her that Tristan is performing. With the help of the basketball team, Miles performs a song of a sincere apology to Maya. Maya tries keeping a straight face, but soon begins smiling and grinning to herself. Miles, seeing that it worked, smiles as well as he finishes the song. He receives a score of 9.8 when the audience and judges sees that he trying to win a girl over.
Following this, Miles and Maya are seen walking into class, holding hands and happy. Winston asks if the singing apology actually worked. Miles says that he is on "probation" and as long as he doesn't screw up again, it should be good. He and Maya begin kissing until Mr. Simpson arrives to take Winston and him down for questioning with the police, stunning them, regarding his party and what happened to Zoe.
In the principal's office, Miles is questioned on what happened between him and Zoe. Zoe is confirmed to have been sexually assaulted at the party and there are photos of him and Winston seen carrying her away - making them the prime suspects. Miles is anxious and simply says he didn't do anything wrong. He asks if he can just go and practice for his upcoming basketball game. They are soon released when Winston confirms how they are seen on several other photos at a different place and time when Zoe's attack took place with time codes on the photos to back it up.
In class afterwards, following Miles and Winston being removed as suspects, Miles is happy at no longer being suspected of Zoe's assault and tells Maya how she can now come to his game and cheer him on. However, Maya is unexcited, lost in thought over Zoe's sexual assault now gone public. She tells him how the pep rally got cancelled due to the suspects of Zoe's assault being on the basketball team. She confronts him over what happened between him and Zoe at his party, asking him about the photos of him and Zoe together and the ones of him and Winston carrying her away. Miles tries explaining things, but Maya asks him bluntly what he did with Zoe. Miles won't give an answer, causing Maya to leave. As she walks off, he insists that he did nothing wrong.Later on, Miles approaches Zoe, having paid her partner to switch. She tells him how she just wants to work on her assignment. Miles tells her how he knows "life sucks for her" right now, but that he wants her to explain how nothing went on between them to Maya, who believes the two might have done something together. Zoe soon asks him if he knows what it's like not knowing what happened to you; not knowing if someone touched you or not. Miles says he can't, but that it's not his fault what happened to her. Zoe says that it sort of is. Miles insists that he didn't do anything. Zoe tells him that's the point; he saw how drunk she was and he just left her somewhere all alone. He asks what else he was supposed to do. Zoe says he could have made sure she was safe and that because he didn't, he let those guys hurt her. In tears, she runs out of class as Miles stares forward in thought.
Before the game, Miles is in deep thought as the team gets pumped up for the game. Tristan complains how the pep rally got cancelled and Miles remarks who even cares about it. Tristan says how he just wanted to have some fun. Miles answers, "Even when someone on this time assaulted Zoe?" One of the teammates brings up how there isn't any proof. Miles says that the people in the video were wearing their team jackets, but Dallas says someone could have easily stolen one of them. Miles tells him how that is nothing but crap and loudly demands for the attackers to come forward. Dallas tells him that they are a team and that they stick together. However, Miles refuses to. Packing up this things, he leaves.
On his way out, he sees Maya nervously walking towards him in the crowd, coming to apologize to him. She said that she overreacted to things, but he insists that she didn't. He says that he knows he screwed up and is sorry. Maya asks if he's playing in the game, but he says that he isn't since the team doesn't care about what happened to Zoe. He suggests that they leave, but she asks if he wants to attend the game to see his teammates' asses get kicked without him. They then see Zoe and go up to her to comfort her over the ordeal. They then watch as Zoe confronts Luke and reveals him as her attacker to the school and Becky walking Zoe off, who is in tears. After Zoe's attackers are arrested, they join in to help Zoe out following the days afterward if anyone gives her any problems. Maya jokingly remarks how she will let Zoe "borrow" Miles for the day to make sure no one bothers her about what happened.
In What It's Like, Miles is carrying a laughing Maya over his shoulder. After she tells him to put her down, Miles asks if he wants to carry her around all day long. He eventually sets her down on a stand advertising for the semi formal. She says how she needs to get her essay done otherwise she's going to be stuck in the Rubber Room forever. Miles complains about how bad it is that she needs to spend first and last period in there. Maya says the sooner she gets her essay done, the sooner she can leave and spend more time with him. He says how he'd like that and the two begin kissing only to be interrupted by Tristan. He remarks if he really needs to see them "suck face". Maya then says she has to finish her essay and opens her bag to get her laptop only to see it gone and begins panicking. Miles suggests she forgot it, but Maya says she would never do that. She then brings up how she left her bag unattended when she went to use the washroom while in the Rubber Room. They immediately suspect her laptop was stolen by one of them.
Miles is later seen sneaking up behind Maya and tapping her on her shoulder, startling her. He laughs and says how he's been looking everywhere for her. He then asks what she's doing sneaking around. She tells him she thinks Zig stole her laptop. Looking over her shoulder, he asks her if she wants him to punch him for her. Amused, she says she needs to make sure she is right first and tries to walk up to Zig. But Miles holds her back, saying how he's likely going somewhere sketchy. She grabs his hand and says that, in the case, he's going with her. The two sneak off and watch Zig break into an abandoned house. Miles suggests he may be squating. After a moment, Maya says that she's going to head home since she has a ton of homework. Miles says he'll walk her home, but Maya she that it'll be out of his way and that she'll be fine. Hesitantly, he agrees and tells her to call him when she gets back.
At school the following day, he overhears Maya telling Tristan and Zoe about how Zig was upset when she approached him in the house. Upset that she lied to him, he says how she told him that she was heading home. Maya says she needed to know what was going on, but he says that something could have happened to her and that Zig could have hurt her. Maya says that Zig of all people wouldn't hurt her. However, Miles insists that he's bad news. It becomes clear that he wants her to stay away from him. Maya says that's her fault since she blew him off all summer long and now he's homeless and that she should have been there for him. Miles, growing frustrated, says that this isn't her problem to deal with. When Tristan sarcastically remarks if she's going to adopt Zig to help him out, Miles tensely suggests, "Or date him?" Maya is a little hurt and he tells her how she seems to care about Zig a lot. She says that's because she has a heart, something the rest of them are clearly lacking. As the bell rings and Maya walks off, saying she's going to talk to Ms. Grell about it, Miles looks upward still frustrated.After school, Miles approaches Maya with a red rose. They both turn around and they both apologize at the same time, with Maya also holding a rose with the same idea. They laugh and Miles apologizes for what he said. Maya explains how Zig was a close friend and that seeing his new dangerous life is scary. Miles asks if she talked to Ms. Grell about Zig. Maya says she was told something would get figured out. Miles says she definitely earned herself a fun night they'll have at the formal together. Maya reminds him how he never officially asked her to the formal. Miles teasingly says he was thinking about his other girlfriend. Maya remarks for him to have a good time with her, smiling at him. The two share a kiss and Miles says how he can't believe he's saying this, but he promised to be home for dinner. After switching roses, he leaves.
In Close To Me Miles shows up at Maya's house with a large bouquet of roses. Maya says to him that she needs to talk to him, but before they do, Miles he gets down on one knee while holding the flowers out. He asks her officially to be his date to the semi formal. After they share a quick kiss, Miles notices Zig in her kitchen. With a troubled look on his face, he says, "What is he doing here?" Maya says, "That is what I wanted to talk to you about" as Miles and Zig stare at each other.
Maya asks Miles, while to school, how many time she needs to say she is sorry. Miles tells how how another guy sleeping in her house, still fuming. Maya ask if he trusts her and he responds yes, but that Zig is the one that cannot be trusted. He brings up how Zig is a drug dealer, but Maya says it is only a rumor. Maya tries insisting Zig is a good guy and brings up the idea that they should all hang out together at the dance. Miles pauses before he says, "You're joking..." Maya says please. He then agrees, saying she is lucky to be cute. He later on shows up at Maya's house again to pick her up for the dance. He compliments her on her dress and she gives him a kiss. As she goes to get her coat and purse, Miles and Zig have a short stare down. He asks her if she's okay and she says yes. The two then leave.
At the dance, Miles says that he's sorry how her plan to have everyone spend time together didn't work out as he dances with her. She says she's over it and that she just wants to have a fun night to spend with her boyfriend. Miles laughs as he tells her to stop stepping on his feet. Maya remarks that he's the clumsy one, not her. He tells her how it's only because he's distracted by his need to kiss her. Maya says there is an easy fix to that and kisses him. The moment is interrupted when Zig approaches and the other Rubber Room kids showing up as well. Maya and Miles are surprised that they came after all. After Zig explains how they snuck in through a side door. After Grace goes off to dance with Tristan, Miles offers to get Zig a drink.
At the punch bowl, the two watch as Maya dances by herself. Miles asks if he saw the game they played. Zig says that he's not into "watching a bunch of meatheads chase a ball around" as they continue watching her dance. Miles says he's just trying to be nice and Zig says not to do him any favors. Miles tells him he's doing it for Maya because he cares. He then says that if he cared himself, he would try as well. Zig, continuing to stare at Maya, says he does care about her... a lot. Miles looks at him and asks him, "As a friend?" Zig says that it's "hard to stay friendly when you sleep down the hall from them". Miles stares at him for a moment before warning him to keep her out of his drug involved lifestyle. Zig says he'll deal whatever he wants, whenever he wants, with whomever he wants. Zig tells him to "play nice" before walking off from a now angered Miles.
Later on, during the dance, Zig is called by school security to open his locker as they have received reports that he is carrying drugs. Miles shows up, asking what is going on. Grace immediately accuses him of being the rat, but Maya insists Miles wouldn't do a thing like that. Miles insists that she is telling the truth, but Grace notices that Miles looked away from Maya as he did so. After Grace tells her that Miles is lying, Maya looks at him in the eye and asks him to tell her the truth. Miles looks away and says that Zig is a huge jerk, revealing himself as the culprit.
As a disgusted Grace storms off, Maya is stunned. She asks "Seriously?" Miles comes up to her and asks for them not to fight now. Maya again asks for him to answer the question. Miles says that he was just worried about her and tries to take her hand, but Maya slaps him away and says how he has no idea what it's like for Zig in his life. Miles asks if she is seriously defending him and tries bringing up what Zig said to him, but Maya ignores this. She rants about how she can't believe he would do something so spiteful just because he got jealous. He then yells at her that Zig is fooling her and she's falling for it. Maya says the only thing she fell for what believing that he could be someone that she could be with. Miles stares at her, now the one stunned, and asks what she's saying. She says she needs time to think, but he concludes she is choosing Zig over him. Maya firmly says it's not like that. However, Miles holds his hands up and says, "Whatever you say" before walking away from a tearful Maya.In Sparks Will Fly (1), Miles sends Maya a gift - not the first - since their break up with a note asking for forgiveness. During music class, he performs a song and is clearly distracted. After the class ends, he is approached by Maya who wants to return it. He says how he knows she told him no more gifts, but he saw the harmonica and instantly thought of her nad that it would be perfect for her. She admits to it being a thoughtful gift, but Miles is upset that she still giving it back. She tells him that he scares her with the way he lashed out at his father and "framing" Zig for drugs. He insists that he can be a better guy and asks for a chance just to prove it. Maya says the only way they can work is if they could keep a relationship between them a secret. Miles is surprised, but accepts it as long as it means getting her back. He tries to kiss her, but Maya ducks, reminding him that it is supposed to be a secret. Miles appears slightly disdained, but smiles at her.
In the hallway in a room, Miles is seen making out with Maya as Winston acts as a look out for Zig. Winston asks if they were done yet, but Miles asks for five more minutes and to just keep an eye out for Zig. As he continues making out with Maya, she says how much she has missed him and he answers that he's missed her too. Winston then sees Zig coming by and warns them in a silly coded warning. Maya gives an distracted, "Hmm?" as the two continue kissing. Winston tries again to warn them, "Black dog is coming!" When Miles asks what he means, Winston yells, "Zig is coming!" The three then act as though they were studying when Zig passes the room, stopping to look at them. He asks if he has interrupting something, which they deny. Zig then requests to talk to Maya privately, causing Miles to look at them. Miles gives Miles a look before she follows him as Miles watches.
Unable to help himself, Miles walks out to watch the two and witnesses from afar as Zig tries to strike up a relationship between him and Maya and even tries to kiss her. As Maya ducks from his advances, she notices Miles who steps closer to the scene. As Zig takes off his bracelet and puts on her wrist as a symbol that she will wait for him, Miles glares at the scene. Maya gives a quick shrug of her shoulders to him, but Miles is clearly angered and storms away.
During music class later on, Maya is singing a song in front of the class that hints close to the love triangle with Miles and Zig. Miles watches as Zig tries convincing Maya to have lunch with him, only to be turned down, and hugs her. As he leaves, he gives Miles a satisfied and cold wink, angering him greatly.
As Maya comes up to him, he instantly declares that he just can't do this and walks away from her. Following him, Maya asks what he means. He explains how he can't stand to see her with Zig, who is openly gloating as if he's won. Maya reminds him that she is with him, not Zig, but Miles reminds her that Zig doesn't know that. Maya tells him she needs him to be the bigger person, but Miles tells her that he can't when Zig has "basically marked her", gesturing to her bracelet. He says that she has been stringing Zig along for a year and asks why. Maya stares at him before she says how she just doesn't want anyone to get hurt. Miles retorts, "Too late for that," and walks out.In Sparks Will Fly (2), Miles is seen at the school dance where Maya asks him if he has seen Zig. He says that he hasn't and is concerned when she shows great worry for him. When Maya tells him how the last person she cared about went missing and never came back, he assures her that things will be fine and he will look for Zig. He gives her a kiss and walks off. Later, he finds Zig in the Degrassi Greenhouse. He tells him how Maya is worried about him and tries convincing him to come inside, only to be ignored. He tells him how he knows that he cares about Maya, only for Zig to claim that he actually doesn't. Miles says that while he doesn't, he cares for her and refuses to let him ruin the dance for her. Zig pushes his hand away when he tries to grab him and Miles walks away. However, Zig then calls Maya his "sloppy seconds". Pausing in his step, Miles then takes a swing at him. A fight breaks out between the two, which ends with Miles beaten and bruised on the ground. As Zig remarks they have broken the "rich kid", Miles yells this isn't over. Zig says it is and walks away.
Later on, Miles is recovering from the fight when Winston shows up with a fake gun that is an exact replica to a real one. As he says the school won't let him bring it in, Miles gets an idea. He takes the gun and decides to approach Zig with it. Winston tries talking him out of it, but Miles refuses to listen. He approaches Zig with the gun, who becomes scared.
As Miles begin threatening Zig, Maya and Tristan arrive, having been looking for them. Maya immediately screams out Miles' name in a panic as they rush up to him. Despite Miles' trying to explain the gun is a fake and that Zig beat him up, Maya reprimands him for doing something so reckless despite knowing how she is already scared of his emotional impulses. As she begins having a breakdown, he tries approaching her only to be pushed away by Tristan. He tells Miles to leave and he does, taking one last look at Tristan comforting Maya, and leaves with Winston.In You Are Not Alone, he is seen teasing Winston about his comic book club he recently started. He asks him why he is running a comic club and Winston claims it is to meet likeminded individuals. Miles flatly tells him that he means girls, to which Winston answers, "Not just girls..." Miles tells him that since it's spring why not just borrow one of his dad's convertibles and go joy riding around to run into some girls. But Winston says he's not interested in "bimbos who are attracted to shiny objects".
Just then they see a girl sign up for Winston's club. He tells Miles, "Hottie alert!" He then rants about how that's a girl who has taste and not afraid in taking risks just as Miles cuts him off with, "That's my sister...", much to his clear disappointment. He asks Miles why his "annoying little sister" is signing up for his comic club. Miles retorts how "a joy ride with bimbo's must not sound so bad now". Winston firmly insists he will meet his "soul mate" in the comic society. He then adds on how she won't be "a comic book character".
Later on, he is seen heavily amused when Winston charges into the Hollingsworth mansion, demanding to know where Frankie is. Miles asks him if he is seriously going to challenge his sister to a fight, saying how she might be able to seriously take him. Winston blows off his comment, claiming he is going to give her a "piece of his mind". Miles says how he is going to go make some popcorn for the show and leaves in a chuckle.
In Enjoy The Silence, Miles walks in on Winston and Frankie secretly discussing their kiss, but doesn't overhear it. He is furious over the fact that his little sister has made out with an older guy, having overheard her talking about it with Keisha. Winston nearly lets it slip that it was him as Miles says she didn't reveal the guy's name. Frankie insists the guy she kissed is nice and Miles doesn't have to worry. However, Miles firmly insists that he knows how high school guys are since he is one and they aren't nice. He declares that this guy needs a good warning. He asks for Winston's back up on his opinion. Winston points out how Miles usually doesn't care about his little sister. Miles says that doesn't mean that he wants some "grade 10 creep trying to feel her up" since she's only a freshmen. He asks if Winston is on the guy's side, to which Winston insists he isn't. Miles then declares that he needs his help in tracking the guy down.
At Degrassi, Miles heads into the computer room fully determined to find the guy who kissed Frankie. After Winston tells Tristan that it was him who kissed Frankie and that he may actually want to date her, Tristan blows off his concerns about Miles being furious with the idea and directly tells Miles that Winston knows who kissed Frankie. Miles immediately demands to know who it is. On a whim, Winston randomly says it was Damon, who is at a computer nearby. He thanks Winston for "finding the perp" and calls him a good friend. However, as he goes to approach him, it turns out he has already left the lab.
Miles is angry that he lost him, but Winston tries insisting it is good thing. Miles retorts if he doesn't believe that he can take him, but Winston calls Damon a "mountain of a man" and doesn't want to see him get hurt. At that comment, Miles suggests they both take him on. Winston tries talking his way out of it, but Miles says they can leave as long as Damon gets the message loud and clear - stay away from Frankie.
Later, Miles looks for Damon and finally finds him in the hallway. He immediately confronts him about supposedly kissing Frankie, remarking how he has to know her age, as Winston tries stopping him. As Miles begins pushing Damon who begins getting ready to strike back, Winston collapses from his sickness. The two both stop and stare down at him. They then carry him off to a hallway bench.After Winston comes to, Miles asks if he is okay. Winston remarks if he is and if Damon hurt him. Miles says he didn't and calls him a surprisingly decent guy. He adds on how he isn't the one who kissed his sister though - Winston is. Winston is stunned and immediately begs for him not to kill him. Miles is amused and asks why he didn't just tell him. He tells him how he was so upset about his break up with Maya that he didn't want to make it seem like he betrayed him as well. Miles asks if he thought that because Frankie kissed him. He then comments how funny he actually thinks it is. Winston asks why he would think that. Miles reveals how Frankie has had a crush on him since she was eight years old and now she's kissed him all these years later. He then blows it off, saying how it's not like he's gonna actually date her since she's in grade nine. He goes on, saying what people would even call them as a couple name and begins making jokes about it, unaware of Winston's hurt feelings since he actually likes Frankie.
Later on, he runs into Maya, who is trying to run out of the hallway, and stops her. He asks her if she's "sneaking off to be with the new boyfriend". Maya tries walking around him, telling him it's not the time. However, he stands in her way as he tells her how people saw her and Zig kissing. He demands to know if it's really that easy for her to get over him. Maya then tells him how he was right about Zig all along, revealing how he is really into drug dealing and is involved in a gang. He asks her if she's told anyone. She says that she can't and tries to leave again, only to be stopped by Miles once again. He tells her how she needs to tell an adult. Maya refuses to since it may land Zig back on the streets and with the gang, possibly dead or in a jail cell. She admits how she feels trapped and can only imagine how Zig himself must feel. Empathetic, Miles assures her that he may have a way out for Zig.
At the bus station, Miles shows up with his father as Maya tries convincing Zig not to leave. As his father tells Zig about being able to get him help from former gang members who specialize in helping other people get out themselves, Miles looks upset as he looks at the two together, unable to look at them and glancing away.
In How Bizarre, he talks with Drew during the campaign work at his mansion home. He tells Drew to slow down in his work, remarking if he keeps working that fast then he will make the rest of the family look bad. Drew retorts that they don't need him to do that. Miles gives a sarcastic "Ha ha" and picks up some posters and leaves.
In My Hero, he is mentioned when Becky talks about Sir Exellence (really Hunter under an online guise) mentioning to her about his "mean older brother". Later, Miles is seen at his house when Drew comes by hoping to talk to his dad. Miles points to him where his dad is coming down the stairs. When Drew accidentially pushes his father into the pool, he laughs while clapping, "Bravo!" and smiling in amusement. When a fellow reporter gives Drew her card for information regarding the incident, Miles looks on in clear concern.
Later on in school, during lunch, Miles teases Drew about "Mr. Popular eating alone". Drew, upset, asks what he wants. As he sits down next to him, Miles asks for him not to talk to the paper about his father. Drew, now smiling, asks what he can possibly tell them about his dad. Miles answers about the affair with Andrea, stunning Drew that he knows about it. Miles tells him how it is best the affair stay under wraps, but Drew says how he was wrongfully terminated and that he can't know what it's like.
Miles reminds him about his father still being a powerful man and therefore can give him something he may want or need instead. Drew asks like what. Miles answers that he must have a lot of powerful connections and can surely come up with something for him. He urges him to at least think about it before getting up and leaving.
In Out of My Head, he is at his locker when Frankie comes up to him and says they need to talk. She tells him how Becky gave her a spot on the modeling team. Miles retorts how that's a good thing, but Frankie says how she doesn't know why she did and suspects their mother paid her into doing it. Miles says how that sounds just like her, making her surprised. Miles tells her how she did the same thing when his little league coach wouldn't make him starter and Frankie recalls how she did tell her how upset she was over not getting a spot. She asks him what she should do. Miles answers to have fun modeling before closing his locker and walking away.
Frankie, following him, says how everyone is making fun of her for being rich. Miles tells her how she shouldn't care what people think and if they want to make fun her then they are going to find a reason. Frankie answers how depressing that sounds and he tells her to "just live her life". Frankie then suggests that she go to Becky and demand an answer and he says, "Sure, or that" before leaving.In Believe (1), he, Winston and Maya are working together on a class assignment. Winston tells him during a debate that just because he wants to have sex with Maya one day doesn't mean he can take her side in the debate. Miles claims that isn't true, unless Maya herself wants to. She retorts, "Seriously?" as she looks at her cell phone at a text she got. Miles assures her that he got the message "loud and clear" before she leaves.
Later on in class, he asks Maya why she seems to be upset. She tells him she can't imagine the pain Zoe must be going through with having reporters stalk her and all the lies about her online during her trial for being sexually assaulted. When she suggests they do something to show support, Miles comes up with the idea for creating placards and shirts and can use leftover campaign stuff from his dad's staff and workers. Maya agrees to it and they agree to meet up later on to get working. Later on, the two are having a good time working and designing shirts and boards. When Maya tells him how much it means to her that he's helping, he says how Zoe didn't deserve to be raped and that people need to hear that.
Maya the tells him how after everything is over, perhaps they can spend some more time together, making him smile. After she leaves to talk to Ms. Grell, Winston tells him that he is only wasting his time. Miles says how he totally has a shot at winning Maya again, but Winston reminds him that he needs to testify in court and how Maya will feel when finding out about his near hook up with Zoe. After class, Miles walks out with Maya after distributing the posters and boards to fellow classmates. When Maya says she'll catch up with him after talking to Zig, he appears slightly disdained, but leaves.
In court later on, he is with the group when Zoe's article badly misquotes her words about the event regarding the aftermath of her rape. When Frankie insists parts of the article are true, mainly about her being obsessed with male attention, she brings up the time she took Miles' rejection of her badly. This brings Miles to ask to be kept out of the conversation.In Believe (2), Miles is seen in the hallways by his locker and he tells Maya that she's the only person he cares about on her opinion if he is a good guy and tells her he loves her and never stopped and they look into each others eyes and when they were about to kiss Winston walks over. At the trial he asked Winston to lie about him hooking up with Zoe at the party so Maya doesn't find out then Maya finds out when Winston is up on trial and she storms out upset and mad and he tells her don't leave me not again and she says this is the last time I'm done we're done.
In Thunderstruck, Miles is asked by Tristan in the hallway about the dance. Miles tells him that the reason Miles isn't going is because of Maya. He invites Tristan to his house for a movie night. Miles and Tristan interrupt Frankie and Winston's date and Miles changes the channel and takes the remote from Frankie. Frankie and Miles argue and start fighting.
They start playing charades and Miles and Tristan keep winning. He makes a joke about Tristan and Tristan runs out into the superstorm. Miles apologizes to Tristan and he protects him from a flying piece of metal. As they're about to kiss, Miles stops Tristan from it by telling him that they should go back inside when the powers goes out
He introduces a new game called Murder. Tristan starts flirting with Miles and Miles starts laughing with him. When he tells them to scatter, Winston tells Miles that Tristan likes him. Miles tells him that they are just friends and he blows out a candle. Later, he finds Tristan back where they started. He scares him and Tristan suspects that he has the lighter and looks for it in his pants. He finds it and tells Miles to stand back or he'll kiss him. Miles is totally fine by the idea and tells him to go ahead and kiss him. Tristan kisses Miles and let's go after that. Miles then leans in to kiss him again, but this time, he makes out with him. They are interuppted by the sound of Winston's flashlight dropping. Tristan leaves the room and Winston confronts Miles about his sexuality and Miles's kiss. Right before Winston leaves, Miles holds up the lighter, revealing that he had it the entire time.
When the storm ends, Miles talks to Tristan about the kiss and how he hurts everyone he cares for. Tristan thinks that the kiss was a stunt to get back at Maya. Tristan tries to leave, but Miles holds his hand telling him not to. He tells Tristan how he feels about him and that he liked the kiss.
In Smells Like Teen Spirit, Miles is at first seen running through the smoking halls of Degrassi with Maya, yelling for Frankie. He stops Shay and Lola, asking them if they've seen Frankie. They shake their heads no, and he continues moving forward, yelling for his sister. Ten weeks earlier, Miles texts Tristan saying to meet him in the greenhouse. They are later seen making out in said greenhouse before Tristan pulls away, asking if they can talk. Miles allows the discussion, to which Tristan says that he doesn't mind having a secret relationship, but he wants to make sure that it isn't all about Maya. Miles insists that he doesn't care about her opinion, and Tristan continues by asking Miles about his dad. Miles jokingly replies with "mood killer" but proceeds to explain that things are good between him and his dad and that he even agreed to do a family photoshoot with his father in order to promote the man's campaign. Tristan asks Miles when it is, and Miles checks the time, realizing that it's in fifteen minutes and that he's going to be late. He runs out of the greenhouse, leaving behind a shocked Tristan.
Miles is next shown arriving at his house, walking into the living room in order to face his family as he raises his hands, insisting, "I know, I know! I'm late!" Mrs. Hollingsworth says that she was worried, and Miles apologizes. His father pulls him aside, and Miles insists that he just wanted to make them happy, and his father tells him not to do anything that needs to be apologized for. He continues by asking Miles where he was, bombarding him with accusations such as "smoking dope or hitting on some girl." Miles, growing fed up with how the conversation is going blurts out, "Making out with my boyfriend!" His family and the campaign workers turn and stare, and an uncomfortable silence follows.
The next morning, he walks into the dining room, saying good morning to his family and making a remark about the "Degrassi renewal project." His father tells him to stop and Miles asks why. His mother is the next to speak though, insisting that they talk about Miles's boyfriend, to which Mr. Hollingsworth makes a remark about how it would be "ridiculous" for his son to be gay. Miles makes a remark about how if kissing people were ridiculous, then they all must be, except Hunter. His brother replies with a "suck it," followed by his mother insisting that he isn't gay and Frankie's questions about his sexuality. Miles shrugs it off, saying that he likes Tristan, until his father interrupts, saying that Miles is just a spoiled brat trying to ruin the campaign. Miles is visibly angry, and he insists that not everything is about the campaign. Mr. Hollingsworth seems annoyed and asks, "Is that what you told your boyfriend?" In a scornful tone. Miles stands up and says, "screw you" before walking away.
The next day, Miles rushes over to Tristan, insisting that the two of them ditch the check ceremony. Tristan seems shocked and asks him about it. Miles says that his father and his "campaign stooges" would be there at any minute, and that he didn't want to be. Miles grabs Tristan's wrist and begins pulling him out of the room in a rush. The two of them are stopped by a reporter asking Miles to say a few words about his father. At first he's reluctant, but he eventually asks Tristan if he could wait for a moment before walking off with the reporter. The reporter asks for the last advice his father gave him, and Miles insists that it's an easy question, because his father's last "advice" had been that being gay is ridiculous.
In Wise Up, Miles' family attacks him over the article in which Miles outed his father as a homophobe, and Frankie says he made dad look like a batman villain who hate his gay son which Miles replies as saying it's all true. Miles's dad walks into the room and asks if he can talk to his son. Mrs. Hollingsworth takes Hunter and a reluctant Frankie to school. Once they leave, Mr. Hollingsworth asks Miles to try out some golf clubs to see if they're the right height for him. Miles is shocked about this and asks his father if they're going to talk about the article. Mr. Hollingsworth tells Miles he's not proud of how he reacted to him and Tristan and says "gay, straight, whatever you are I just want you to know that I accept you."
Later, Miles and his father are seen at the course, in which they're talking about his first pair of clubs, Spiderman, to be specific. Mr. Hollingsworth laughs, insisting that he remembers those same clubs going through the pool house window. Miles replies with a laugh, saying that he was playing Spiderman and that he was seven years old at the time. Miles continues by asking his father what all of this is about, saying that he humiliated his father in the newspaper. Mr. Hollingsworth insists that sometimes he feels like he knows nothing about Miles, being that he is his eldest son. Miles says it's because they're always fighting, and his father replies, saying that they need to work on that. The two share a hug, but then the press shows up, snapping a picture. They ask Mr. Hollingsworth for a comment, to which he responds that it's difficult when a child comes out of the closet, but he's working on it. He says that he hopes the LGBT community understands and asks, "Right, Miles?" To which his son shoves his hand away, storming out of the room.
Mr. Hollingsworth heads back home to see Miles sitting on the couch, a game controller in his hands. He asks Miles what's wrong with him and says that he made a mockery of him. Miles seems upset by this, and he starts yelling about how his father acted like he wanted to spend time with him, but it was all for the press. He insists that all his father ever does his manipulate everything and that he can't believe he fell for it. Miles begins to storm away, and Mr. Hollingsworth asks where he thinks he's going. Miles replies with, "to school, where at least one person gives a crap about me!" Mr. Hollingsworth begins to yell and grabs his son, shoving him against the wall. Miles's back is clearly injured, and Mr. Hollingsworth pulls away, apologizing and insisting that it was an accident. Miles asks if he can go to school now, and his father lets him.
Miles walks into a classroom and finds Zoe and Winston, asking them if they've seen Tristan. Zoe points out how Miles suddenly likes guys, and Miles replies with "just one" and asks if they know where he is. They tell Miles that Tristan doesn't want to see him after he outed their relationship in the newspaper and that everyone is teasing him to which Miles asks why. Tristan appears and says because they think he is just using Tristan to piss of his dad, Tristan tells Miles that he promised to keep their relationship a secret until they figured things out, and Miles tries to explain but Tristan tells him he doesn't want to talk to him right now. He says that he thought Miles actually liked him but he only manipulated Tristan. Miles is upset to hear this, insisting that he doesn't manipulate people and that he needs to speak to Tristan. The bell rings and Tristan goes to his seat. Zoe and Winston stand in front of Tristan's desk so Miles can't get to him, and Miles sees that he's beaten so he bails out of the classroom.
Maya confronts Miles as he storms down the hallway, wanting to talk about the fact that her "ex starts making out with my ex best-friend" and that she deserves a conversation. Miles tells Maya to leave him alone, and he storms into the boy's locker room, slamming his books down onto a table. Maya walks in on Miles about to cry, and he points out to her that this is the boy's locker room. She says that she doesn't care and asks if he's doing this to hurt her. He says that she thinks a lot of herself, and she insists that she just wants to know what's going on because she's confused. Miles replies with an angry, "You're confused?!" and turns away. Maya asks him what's happening, and Miles says that he is and "the great tornado that is Miles Hollingsworth III is screwing up his life again." Maya asks him if he had another fight with his dad, to which he responds that he should find Tristan and begins to walk away. Maya stops him and says that if something's going on then he should talk about it, even if it isn't with her. She insists that if you keep everything inside your head, then it only gets worse.
Miles is later shown walking into a room of his house, asking Frankie and Hunter where their mother is because he needs to talk to her. Hunter says that he doesn't know, but their father locked himself in his study. Frankie asks what happened this time, and Miles says that that's what he has to talk to their mother about. Frankie asks if they got into another fight, and Miles confirms it, followed by Hunter's remark of, "didn't like the course he took you to?" Miles tells his siblings about how it was all just a photo op, not some "bonding expedition." Frankie insists that he only looks on the worst side of things and that he and his father love each other. Miles asks if they're living in some alternate universe, to which his siblings point out to Miles that he's just like his father, though Miles insists that he's nothing like him.
Miles walks over to his mother, pointing out that his road test is in twenty minutes. She asks Miles what happened at the golf course, to which he replies, "What always happens. We fought." She points out that she was told he made a scene in front of the press and that he should apologize to his father. Mr. Hollingsworth appears, insisting that wouldn't be necessary. Mrs. Hollingsworth says that they have to deal with the situation, but her husband just walks over to Miles, insisting that the stress of the campaign has taken a toll on him and asks if they can start fresh. Miles says he doesn't know, and Mr. Hollingsworth accepts this, saying that they should start with a simpler question then: "black or silver?" Miles seems confused and follows his father out into the driveway where two expensive cars sit. Mr. Hollingsworth says that he doesn't think Mrs. Hollingsworth will let him keep both, so he'll have to choose.
Miles arrives at school in his new black car, and he approaches Zoe, Maya and Tristan. Zoe asks him about the car, and he tells them that his dad got it for him and how they're in a "better place" now. He points out how his father would also like his "boyfriend" to come over for dinner and asks Tristan if he still has one. Tristan says that depends on if will a ride be provided in the car, and Miles replies with "if that's what it takes." Miles then smiles and walks up to Tristan, kissing him. Miles ask if he's forgiven, and Tristan points out how he's happy that Miles worked things out with his dad. Miles proceeds his arm around Tristan, and the two begin to walk towards the school together. Before they can get inside though, Maya stops Miles and asks what he's doing. He pulls off his sunglasses and gives a dead looking smile, saying that "he's making things better."
In (You Drive Me) Crazy Miles learns that Maya hacked into his facerange account and broke into his house to make sure he was alive. He then blocks her from his facerange.
In I'll Be Missing You Miles and Tristan are paired together on an assignment but he bails to do pot.
- He came up with Winston's nickname "Chewy". It is a name Winston has said he hates, but Miles continues to call him it. It is also said that he and Winston have been best friends since they were five years old.
- Miles is the first character in Degrassi History to be named directly after his father and grandfather.
- He was kicked out of boarding school for starting a fire.
- Miles's father is running for mayor in Season 13.
- He smokes marijuana and occasionally drinks. It is implied that his father is aware of his habits and lifestyle, but does not care to intervene. While he has gotten drunk during his time on the show, it is unclear if he still smokes marijuana.
- In Summertime we learn Miles has a credit card, his pin is 1562.
- His Twitter.
- He shares many similarities with past Degrassi students, like Declan, Fiona, Peter, Sean, Darcy, Ellie and Craig. As well as Maya's now deceased ex-boyfriend Cam, and current Degrassi character Eli.
- He is the fifth character to have an abusive father, the other four being Rick, Liz, Craig, and Jane.
- He is the first character to have an abusive father whose abuse is verbal; not physical or sexual.
- He has one sister, as confirmed in My Own Worst Enemy, who is seen in You Got Me. It is later revealed he also has a younger brother, who is his sister's twin, who is seen in No Surprises.
- He took a hip hop class when he was younger until his dad took him out of it upon learning about it.
- Miles is one of the six non-homosexuals to be crushed on by a homosexual. The other five were Griffin (by Marco), Peter (by Riley), Holly J. (by Fiona), and Cam (also by Tristan).
- Miles is the second of Maya Matlin's boyfriends to be crushed on by Tristan. The first was Cam.
- He is the first boyfriend of Maya's to actually date Tristan, however.
- In Barely Breathing, Miles claims that he has kissed more than 50 different girls, (including Zoe).
- He is the fourth character to catch their parent having an affair. The other three are Caitlin, Emma, and Jimmy.
- He is, so far, the only character in his class to have a drivers license and a car (as seen in the Dress You Up mini).
- According to Frankie, he had a girlfriend who sneezed weird, which caused them to break up.
- So, far on the show he has shared kisses with Zoe, Maya and Tristan, all whom at one point or another have been friends.
- He had a conflict with Zig Novak.
- Miles is the first male bisexual Degrassi student and the second bisexual male in the franchise after J.J., a NYU student Eli knows.
- His first on-screen kiss was with another guy, Tristan Milligan. This could have been foreshadowing about Miles' future plot of him questioning his sexuality.
- When he was seven, Spiderman was Miles' favorite as revealed in Wise Up.
- (To Maya): "Nice try. But, it's not gonna work." (First line)
- (To Maya): "Looks like we will spend the summer together after all."
Maya: "I'm here to spend it with my best friend. Not you."
Miles: "Your loss."
- (To Maya and Winston): "Now what should we do for an encore? Swim?"
- Tristan: "I was just thinking about-"
Miles: "My abs?"
- (To Tristan): "Boo hoo rich kid, right?"
- Maya: "Now look at what you did." Begins walking away.
Miles: Wait, wait... are you sure you don't want to kiss me?"
- (To Maya): "I knew you'd come crawling back."
- Zoë: "You look hot like that."
Miles: "Like what?"
Zoë: "Like that... I don't know."
- (To Maya): "Don't say I never did anything for you."
- Tristan (after locking Miles in a mock-pillory): "While locked in the pillory, crowds would gather to laugh, point and throw rotten fruit at the criminal. Anyone have any grapes?"
- (To Zoë): "I'm a man of my word."
- (To Winston): "Jeez, Chewy, you've been here for an entire year and it's not like any of these girls even know you."
Winston: "Trust me, none of these girls are worth knowing."
Miles (sees Maya sitting in a nearby row): "I don't know, there might be one or two worth checking out."
- (To Tristan): "Do I scream 'homophobe' or something?"
- (To Zoë): "Let me put this in TV terms so you'll understand. I don't do re-runs, especially with mean girls like you."
- (To Zoë): "Your uh, boyfriend doesn't even know your name."
- Maya: "Hey, are you mad at me?"
Miles: "Why would I be mad at you?"
Maya: "Because that boy in the video...?"
Miles (after a moment): "It's not like you're my girlfriend."
- (To Tristan): "I better make starter."
Tristan: "Starter? Isn't that a little ambitious for a sophomore?"
Miles: "Yeah, try telling my dad that."
- Miles taps on Maya's window.
Maya (opening the window): "What are you doing here?"
Miles: "I just wanted to apologize. I feel like I pushed you to do that song."
Maya: "Zoë ruined my life. She deserves it."
Miles: "She's just jealous because you are talented and funny and awesome in ways that she'll never be."
Maya: "You don't have to say things to make me feel better."
Miles: "I'm not. Trust me." Miles kisses Maya "School is going to suck without you."
- Tristan: "I love your house, Miles. It's very Real Housewives."
Miles: "My mom keeps re-decorating it over and over. I think she's just bored."
Winston: "Bored and hot."
Miles: "Dude, gross."
- (Miles to Zoë): "I can't believe you showed up here, and you brought a narc."
Drew: "I'm not a narc!"
Miles: "Dude, you're like 30. Why else would you be here?"
- Andrea: "Why don't you tell me how your dad has influenced you."
Miles: "Honestly, I think the most crucial thing he's taught me is how to juggle. Tasks, priorities, affairs..."
Miles Hollingsworth II: "I think he means business affairs, for the record."
Miles: "That's what they call it? Well, then, business must be pretty good then, Dad!"
- Winston: "Be the hero of your own story! Join comic book society today!"
Miles: "And never get any action!"
Winston: "Dude! I am trying to attract com members!"
- (To Drew, about pushing his dad into the pool): "Bravo! Ten out of ten!"
- Tristan: "Come any closer, and I'll kiss you."
Miles: "Go ahead.
- Miles: "I'm confused Tris. It was weird."
Miles: "But good weird. I just know that I feel good when I'm around you."
Miles: "So, what now?" Thunderstruck
- (To Mr. Hollingsworth II): "Making out with my boyfriend!" Smells Like Teen Spirit
- Main article: Miles-Zoë Relationship
- Zoë Rivas
- Main article: Miles-Maya Relationship
- Maya Matlin
- First Relationship:
- Second Relationship:
- Third Relationship:
- Main article: Miles-Tristan Relationship
- Main article: Miles-Maya-Zoë Love Triangle
- Maya Matlin and Zoë Rivas
- Main article: Tristan-Miles-Zoë Love Triangle
- Tristan Milligan and Zoë Rivas
- Main article: Zig-Maya-Miles Love Triangle
- Maya Matlin and Zig Novak
Adam • Alli • Anya • Arlene • Becky • Bianca • Campbell • Chantay • Clare • Connor • Dallas • Dave • Declan • Drew • Eli • Fiona • Frankie • Grace • Holly J. • Hunter • Imogen • Jack • Jake • Jenna • Jonah • K.C. • Katie • Leia • Lola • Luke • Marisol • Maya • Miles • Mo • Owen • Peter • Riley • Sav • Shay • Snake • Tiny • Tori • Tristan • Wesley • Winnie • Winston • Zane • Zig • Zoë