|Intimacy Level||Best Friends|
|Friendship Started||10 Years Before Summertime (1301-02)|
|Friendship Status||Best Friends|
In Summertime, Winston is at Miles' house for a party for Miles' father Miles Hollingsworth II. Miles introduces Maya Matlin to Winston, and calls Winston by his nickname, Chewy, when introducing him. On the balcony, Miles offers Winston and Maya some alcohol. Maya accepts but Winston refuses. When Maya accidentally drops the bottle, Winston tells Miles that maybe his dad won't be so mad. Miles tells Winston that he knows more than anyone that his dad will be mad. When Miles' dad is yelling at him inside the house, Winston tries to make conversation with Maya and tells Maya that Miles' dad will stop yelling at his son, soon. Winston and Maya try to stop Miles when Miles flips out and jumps into the pool with his clothes on. Winston jokes and tells Maya that she should probably "go fish him out" but Maya tells him that she doesn't want to be around guys like him and leaves the party, leaving Winston standing there on his own. Miles and Winston then appear on the bus for Paris, where they once again, run into Maya.
In All I Wanna Do, when Tristan pretends to be straight, they both laugh at him, making Tristan assume they're making fun of his sexuality. Miles later clarifies that they were both laughing because they knew he was gay and found it funny that he was pretending to be straight.
In About a Girl, Maya asks Winston to tell Miles to stop making out with Zoë all the time. He tells Maya that if you tell Miles to stop doing something, he'll just do it twice as much.In Cannonball, Miles and Winston are both seen trying to get dressed and hitting each other with their clothes until Maya walks in to ask them where Tristan is, and they both don't know. Miles seem to be upset when Maya chooses Winston over him to help find Tristan. Later, Maya finally goes with Winston to ask Miles for help. Winston seems to be annoyed that Miles is going along with Zoë to make Maya beg on her knees to ask for help. In class, Winston laughs as Maya and Tristan use Miles to show how in France, they used to behead people as a form of punishment for petty crimes.
In This Is How We Do It, he is walking in the auditorium and trying to greet a couple of passing girls, who ignore him. Miles remarks how he's been there for a whole year and yet not one single girl knew who he was. Winston says that none of the girls there were worth knowing. Miles, seeing Maya in the crowd, however tells him that there might one or two worth checking out.
In You Got Me, he is seen entering the school Beach Bash alongside Miles. He complains about the lack of music and asks how he's supposed to do his "sweet moves" is there is no music. He tries doing some dance moves silently, but Miles stops and remarks how "that" is the reason he doesn't have a girlfriend.
In Sparks Will Fly (1), Miles and Winston are seen with Maya and Miles, and he is warning them that Zig is coming.
In Sparks Will Fly (2), Miles and Winston are seen together when Miles takes his fake gun. He says, "Man, what are you doing?" Miles responds, "Relax, Chewy. I'm just going to scare him, ", which Winston thinks isn't a good idea.
In You Are Not Alone, Winston is seen talking to Miles about wanting a girl that's into comics and is not afraid to take risks, and Miles says he can borrow his dad's car to get girls. Winston responds he doesn't need a car to be impressed with a car and get bimbos. He sees a girl signing up for his club and is attracted to her, but Miles tells him that it is his sister, Frankie, signing up for his club. Later, when Winston comes to the Hollingsworth house to confront Frankie, Miles is amused and comments that he was going to make popcorn to watch this. However, while he was gone, Frankie and Winston end up kissing, which they agreed that Miles could not know about.
In Enjoy the Silence, Miles and Winston are seen talking and Miles wants to know who kissed Frankie and is determined to find out who did. Then Miles found out it was Winston who kissed Frankie and Miles tells him about how Frankie has had a crush on him since she was 8 years old.
In Believe (1), Winston is talking to Miles about Maya and says what is he going to do when Maya finds out he cheated on Maya with Zoë at the party.
In Believe (2) Miles tells Winston to lie about him hooking up with Zoë at the party that night so Maya doesn't find out and break up with him again. But then he decided to tell the truth when he was on trial.
In #RiseAndGrind, the two discuss their sexual history after playing truth or dare with Zoë and Tristan. Winston thinks Miles makes people feel bad for being virgins and doesn't want him to pressure Tristan into sex.
After Tristan and Miles have sex Winston and Zoë ask Miles about it. Winston reads between the lies and teases him.
- Miles: "Look Frankie, I know high school guys. Okay, I am high school guys. We aren't nice. He needs a warning. Right, Chewy?"
Winston: "Um, you usually hate your sister."
Miles: "That doesn't mean I want some Grade 10 or 11 creep trying to feel her up! She's in Grade 9!" - Enjoy the Silence
- Winston: "So, maybe there's a silver lining to walking in on your mom getting--"
Miles: "No! I think I have PTSD. I want to murder that rando my mom was with."
Miles: "I think that cutting the brakes on his car might really help me heal from this trauma."
Winston: "That's what I'm talking about."
Miles: "Or maybe decapitation? I have some antique swords kicking around the house."
Winston: [laughs] "Well, there you go."
Miles: "I've also heard that bathing in the blood of your enemies is very therapeutic."
Winston: "Hmm." - #NoFilter
- Winston: "So, are you gonna tell your brother and sister?"
Miles: "Nah, if my mom is having a fling, Frankie and Hunter don't need to know. I'm just gonna forget what I saw. Or, you know... murder." - #NoFilter
- Miles: "My mom thinks I'm a bad guy."
Winston: "Yeah, my mom thinks I'm a bad cook. Sorry your problem's bigger." - #YesMeansYes
- Miles and Winston have been best friends since they were five years old.
- Winston knows that Miles' father abuses him.
- Miles typically calls Winston by his nickname "Chewy."
- They are both friends with Tristan Milligan, Zoë Rivas, and Maya Matlin.
- They both disliked Drew Torres though both are on good terms with him.
- Winston was secretly dating Miles' younger sister, Frankie. However, he knows now.
- Miles feels that Winston betrayed him in court.
- Winston has told Miles that he's a mess, and that he hurts people he cares for.
- They were both members of the French Club.
- Winston does not like Miles and Esme friendship.
- They both dated Zoë Rivas.
- When Tristan and Miles first started dating Winston was upset that they were hanging out so much.