The conflict between Miles Hollingsworth III and Miles Hollingsworth II has been going for years. They don't have a father and son relationship. The dislike on Miles lll's side started mainly when he discovered Miles II was having an affair with Andrea.
In Summertime, Miles II's first appearance was scolding his son, Miles Hollingsworth III at a concert that he, Tristan, Maya, and Zoë had attended. Later Miles II has a brief interaction with Maya about his son who he then sees taking liquor from the table. He jokingly talks to him about it which shows that he may be fine with the idea that he is drinking. But when Maya accidentally drops the liquor bottle from the above grounds, Miles II angrily takes his son in a room where he yells at him.
In Everything You've Done Wrong, when Tristan reveals he gave Miles fake steroid pills, Miles gets angry at him because now the team would think he stupid, which he mentions is how his father thinks of him.
In No Surprises, Miles II catches Miles III skinny-dipping in the pool and yells at him to get out. Later in the episode, Miles III catches his father having an affair with his campaign manager and tells his mother about it, only to discover that she already knows about it.
In Basket Case, Miles III throws a party to get back at his dad after he leaves for a weekend. He blackmails his father into letting him out of the campaign.
In Wise Up, Miles II asks his son out to go to a golf club. As Miles III realizes that his father called the press he gets angry and leaves. Because of Miles III's behaviour they get into a fight at home where Miles III gets pushed against the wall by his dad. After that, Miles III asks quietly if he can go to school now.
After asking if they both can start fresh again, Miles II says to his son that he can choose either a black or a silver car to take on his road-test.
In Firestarter (2), Miles is first seen at his house playing video games as his dad comes in and asks about Frankie. Mr. Hollingsworth II says then that he will not going to let his kids ruin his campaign for which he had worked for years. After that Miles asks if he would rather be a mayor than a good father. Miles II responses he gives them kids everything but Miles III corrects him that he gives them everything except love, respect or common decency. Because of that Mr. Hollingsworth smashes a cup against the wall which nearly hits Hunter. Miles III says than that his dad doesn't care who he hurts. After that Miles gets hit by his father. After his father leaves because of an incoming call, Miles goes to Hunter and asks him if he's okay. Miles then says that something like that can never happen again. As Miles tells his mother about what had happened and that his father hit him intentionally, she doesn't believe that Miles II could hit his son out of the blue. Hunter confirms then that Miles did push his father first.
As Mr. Hollingsworth works on his campaign Miles shows up and tells his dad that he thinks he wouldn't care about them. His dad denies it and tells him he'll try harder to make things work between them. But Miles doesn't accept his apology and tells his dad that he wants him to move out. After responding that Miles III is talking nonsense and that maybe he is the problem, Miles III raises his fist about to hit his father. Mr. Hollingsworth request him to hit him whereupon Miles III stops because he couldn't do it like his dad does. After that his dad leaves saying "Yeah, just as I thought."
Degrassi: Next Class
In #YesMeansYes, Diana invites her husband to a family dinner with her kids. Miles ditches the dinner, but runs into Miles II as he is leaving. Miles II tells him he wants to earn back his trust. Miles tells his mother never to let him back into their lives, but she tells him they are planning another family dinner. Later, Miles breaks into his father's apartment to try and find evidence that he hasn't changed.In #ButThatsNoneOfMyBusiness, Miles agrees to go watch Hunter's video game team, even agreeing to go knowing Hunter wanted their father there. Miles admits to Mr. Mitchell that his short story is about his dad. Miles could not handle talking about his father without the anxiety pills Esme Song had given him. He and Esme steal some from the girls locker room, though the pills were a higher dosage than Miles was used to. He takes them anyway and becomes very high, causing him to act strangely at Hunter's video game competition, even acting friendly toward his father. Miles II does not notice that Miles is on drugs.
In #ILookLikeA, Miles II and Miles III are attempting to rebuild their relationship. Miles II is overjoyed to hear that his son got accepted Queen's Commerce, his alma mater, and gifts his old jacket to Miles III. Miles III brings up that he also has an interview for a writing program in London, to which his father states that it is a hard career to achieve success and wealth in.
In #Obsessed, Miles III cannot afford to go to the London Writer's Academy because he believes that Miles II thinks that writing is just a phase, but he still has not asked his father. Later at home, Miles III asks his father to support him in his academics in London. Miles III explains his plan to cash in the tickets for the Europe trip, work as a lifeguard, and borrow some money from his father just to attend the program. Miles II is willing to open Miles III's trust fund for him to use, after seeing how much the program means to him. Miles II tells his son that he is proud of him, something that he has never told him before.
- Miles II is abusive towards Miles III both verbally and physically.
- They were both named after their father.
- Miles III knows Miles II was cheating on his mom with another woman.