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|Intimacy Level||Former Rivals, Acquaintances|
|Friendship Started||How Bizarre (1333)|
|Friendship Status||Good terms|
Season 13In Dig Me Out, Miles is at his house, throwing a pool party. Miles is seen flirting with Maya before noticing Drew and Zoë arriving. Miles retorts how he didn't expect Zoë 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 Zoë to stay. This threat silences Miles, who stares at Drew. Maya comments on Drew's method of blackmail and remarks that he and Zoë are made for each other. Miles' walks off as Maya follows behind him. Later, Miles challenges Drew and Zoë to a game of chicken pool fighting, but is declined.
In Basket Case, Miles talks on the phone with Maya, his girlfriend, until his father then walks in alongside Drew. He asks 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. Miles says they are going to be throwing the party. 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 and is away until he finds out that Miles tricked him and storms back to the house.When Drew arrives, he sees Miles on his way out. He 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.
After the party and the following morning, Mr. Hollingsworth comes home and sees the mess. Becoming furious, he asks where Drew is since he had been assured 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.
In How Bizarre, Miles 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 they don't need him to do that. Miles gives a sarcastic "Ha ha" and picks up some posters and leaves.
- Both have dated a Matlin sister.
- Both have dated Zoë Rivas.
- Drew had a conflict with Miles' friend Winston Chu.
- Drew used to work for Miles's father, during his campaign for mayor.
- Drew was suppose to keep an eye on Miles and the house, the night of the big party, where Zoë Rivas was raped.
- They were both members of the Degrassi Basketball Team.