|Nickname||Esmiles, Hollingsong, Mesme|
|Intimacy Level||Enemies, Ex-Friends with Benefits, Former Mutual Attraction, Mutual Dislike|
|Friendship Started||#YesMeanYes (1503)|
Tired of listening to Miles complain about his family issues in class, Esme cuts her own hair and blames Miles, earning him a detention. Esme not only did to keep Miles from having to see his father, but also so she could spend time with him. She later talks him into breaking breaking into his fathers apartment, where they hook-up. Esme starts feeding Miles drugs, claiming that they will make him feel better, to which he soon develops an addiction. When Miles tells her to stay away from him as she is making his life worse, she responds by faking a suicide attempt to get his attention. Their friendship ends, and the two are not on civil terms.
Season 15In #NoFilter, Esme and Miles are in the same English class. She doesn't speak, but pays close attention to Miles.
In #YesMeansYes, in English class, she frames Miles for cutting off her hair, and he gets detention. She later reveals she did this because he was talking about he didn't want to go home to have dinner with his father. Esme tells him to get proof since he believes his dad can't still be trusted. Esme goes with Miles to break into Mr. Hollingsworth's apartment, and they find an email Miles's father sent to Andrea, whom he was having an affair with, asking her to stay away from him. Their investigation is cut short when his father's cleaning lady shows up, and they have to hide in a closet. Esme initiates a kiss with Miles, and they make out.The next day, out the front of the school, Esme gets Winston to leave and realises Miles told Winston that they made-out, Esme holds his hand and asks how she can put a smile on his face, he says convince my mum to dump my dad. Esme tells Miles there will always be peple in your life that upset you, they sit down on a bench. Esme tells Miles to find a way to control his feelings, and she gives him anxiety pills, Hunter briefly interrupts to tell Miles to come meet them in the car, Esme tells Miles to take 2 pills and call her in the morning before kissing him on the check and bailing.
In #NotOkay, they are seeing flirting with each other in the hallway. Later, they run into Tristan when he is about to go on his date with Vijay and tease him about it. Tristan questions their relationship and they say they identify as siblings, but then kiss each other. While Tristan and Vijay are on their date, Esme and Miles are both seen laughing at them in the background.In #ButThatsNoneOfMyBusiness, Esme gives Miles more pills in class. He sits next to her and Winston starts to question how he's getting through things before finding the drugs. He asks what they are and Esme says they are lorazepam. Winston tells Miles they can be super addictive, Esme asks if they help?, Miles says he doesn't want to take them forever, Esme says why not and Miles asks what will happen if he stops taking them. Esme jokingly tells Miles that if he tries to get off the anxiety pills for good, he will spontaneously combust and have withdrawals. In a more serious tone, she then tells him that he'll go back to being a mess every single time someone mentions "daddy". Winston tells Miles he's as messed up as Esme is if he keeps taking the drugs.
After Miles decides to go off the pills, he collapses and calls Esme. She tells him that he's having a panic attack and how to relieve himself from it. They later sneak into the girls's locker room to steal anxiety pills since Esme believes that girls in grade 10 will most likely have them. After they find someone's prescription, Esme tells him how to take them and he does. Later, they smile at each other in class when Mr. Mitchell tells the class their assignment is reading Miles' story. After Winston tells Miles that him taking the pills is dangerous, Miles says that Esme is currently the only person that cares about him and she smirks and they walk out of class while Miles holding her shoulders.
In #SinceWeBeinHonest, In a classroom, Esme walks in and spots Miles and quickly covers up her sleeve, Miles watches her from afar looking concerned.After Class, Miles cashes after Esme and confronts her in the corridor, Esme says to leave her alone, Miles asks what she did, Esme says he wanted her out of his life, Miles says you hurt yourself because of me, Esme says she gets a bit crazy when she's alone with my thoughts, Miles says he shouldn't of ditched her, Esme says you wanted to get better, Esme starts crying and Miles hugs her, Esme says she misses him and that everything was easier when they were together, they pull apart from the hug, Miles says they should get lunch, Esme says didn't you have somewhere to be (meaning Tristan), Miles looks over at Tristan and then says no and they hold hands as they walk outside.
Later, Miles is walking the hallways with Esme and has his arm around her, he tells her to go to the cafeteria and save them a seat. Esme finds a seat and waves at Miles who's talking to Tristan. Miles watches Esme from afar.Outside, Esme and Miles are sitting down, Miles asks how she is feeling, Esme says she's stressed about the exam, Miles brings up his therapist and thinks he could help Emse too, Esme says she already talked to a shrink, Miles is confused why he let her come to school since self-harm patients are kept for 72 hours under observation and Miles realizes Esme lied to him about harming herself, Esme takes off but Miles catches her saying she faked a suicide attempt, Esme says she had to as he was ignoring her, Miles says he can't believe he let Tristan down for this, Esme asks why is he trying to live up to impossible expectations, Miles tells her to stay away from him, Esme says she doesn't have anyone else, you're the only one who ever let me feel normal, there wasn't something that needed to be therapist-ed out of me, Miles says don;t make this harder I'm trying to change, Esme says he doesn't need to change for her, doesn't it feel like everyone wants us to be someone they're not, Miles says sometimes, Esme says there's nothing wrong with us, Miles says what are you saying, Esme asks Miles to run away with her.
In #BreakTheInternet, Esme is present in Mr. Mitchell's class that Miles also takes. After Miles complains to the class about being blocked from the Degrassi page, Esme smugly states she is glad his posts are not on her feed anymore. When Miles announces to the class that Tristan had grasped his hand while in a coma after the bus crash, Esme was quick to correct him that it was probably a simple involuntary gesture from leftover responses in the nervous system. She is quick to squander his hope over Tristan's recovery, probably because she is still hurt over her previous encounter with Miles in #SinceWeBeinHonest. Later, when Miles gives his disturbing presentation over his summer spent in the hospital watching Tristan's procedures, Esme tells him he "is a sadist." In retaliation Miles says that "just because everyone leaves you doesn't mean that Tristan will leave me." Triggered by the loss Esme has had with her Mother and with Miles' friendship, she lashes out and shoves him. Zig holds her back to stop the altercation.
In #WorstGiftEver, Miles, who is working as a waiter at Lola's Cantina, brings Esme and Zig's food to them at their table. Esme, taking the opportunity to insult him, comments on how fast Miles has lost interest in Tristan and taken an interest in Lola. Miles, upset, fights back by saying that not every occurrence between two people ends with "homebase."
In #ImSleep, Esme complains to Zig her reluctance to go to Miles' play.
- Esme gave Miles anxiety pills.
- Esme dislikes Miles' best friend Winston Chu.
- Esme pretended to hurt herself to get Miles back.
- They have both kissed Zoë Rivas.
- Miles was in a conflict with Esme's boyfriend Zig Novak.
- Esme was in conflicts with Miles' boyfriend Tristan Milligan and ex -girlfriends Maya Matlin and Zoë Rivas.