Esme and Winston first met in Season 1, when Esme told Winston and Miles to be quiet during class. Their conflict began after Esme started feeding Miles drugs, telling him that they would help him cope with his problems at home. Winston saw how quickly his best friend was sinking into addiction, and dangerous behavior and immediately began feuding with Esme over his well-being.
In #YesMeansYes, Esme tells both Winston and Miles to be quiet because they are talking in class. Later, Winston asks Miles the details of him and Esme's kiss and when Esme goes to talk to Miles, she gestures to Winston to go away.
In #ButThatsNoneOfMyBusiness, Winston becomes concerned with Miles' pill use and warns him that he could "be as messed up as Esme is" if he continues to take the pills. Esme then explains to him that the pills are harmless. Later, Miles tells Winston that Esme is the only person that cares about him and Esme sarcastically smiles at Winston in response.
In #BuyMePizza, Winston promises Esme a spot in the school gala until Zoë kisses him, and he gives it to her.
In #ToMyFutureSelf, Zoë dresses as a geisha and Winston dresses as a Japanese soldier, and they receive backlash from Esme for being racially insensitive. After apologizing to the class, Winston confronts Esme as no one was really angry at him, a Korean, for dressing up as a Japanese soldier. Winston emphasizes that she should know that there is not only one kind of Asian. Esme replies with "my bad" and walks away.
In #IWokeUpLikeThis, Esme pulls grabs Winston and suggests that they have sex in the hallway.
- They have both kissed Zoë Rivas, only Winston was in a relationship with her.
- They both have been in a relationship with Frankie Hollingsworth.
- They are both friends with Miles Hollingsworth.
- Winston has implied disapproval of Esme's friendship with Miles.