Work Text:
It takes Oliver almost a year to discover the existence of Stiles. Rationally he knows that he’s been preoccupied with trying to rebuild QC’s reputation from the ashes of the Undertaking and that transitioning from The Hood to The Arrow while dealing with Laurel and Sarah and not dealing with Tommy, but it still alarms him that a boy has been in Thea’s life for years and he hasn’t known about it.
As far as hormonal teenage boys go, Stiles isn’t too bad. He babbles almost as much as Felicity does and it doesn’t take Felicity long to assure him that besides from showing up to crime scenes and being in his arm’s length of police reports, the kid isn’t too bad. His father is a Sheriff which explains most of the stuff to do with the police reports and the crime scenes. The only thing Oliver really worries about is that the kid locked his class mate in a stolen police van for a few days. Thea hadn’t said much other than it was funny and that Jackson was an asshole and had totally deserved it. Oliver doesn’t know who Jackson is but his parents are rich lawyers, hence the restraining order that has apparently been retracted, and that he and Stiles “totally get along now”.
Stiles and Thea watch Mean Girls together and eat ice cream while wearing face masks every Sunday morning. It’s weird but Oliver knows how persuasive (terrifying) Thea can be and settles with being relieved that he doesn’t have to do any of that with her. There’s only so many times he can watch Mean Girls without wanting to cry. Stiles doesn’t seem to share his plight though and only seems to draw the line at waxing hair off his body.
Another thing that Oliver doesn’t totally understand is the fact that Stiles and Roy get along, really well. He doesn’t understand it because Roy and Thea are Roy and Thea but at the same time there is also Stiles and Thea; Stiles and Roy; and Stiles, Thea and Roy. Oliver has no idea how it works but Diggle’s pretty confident his sister isn’t in a threesome or polyamorous relationship and Oliver doesn’t like to think about his sister like that because Thea is always going to be twelve and think boys are icky in his mind. So he’s not sure how any of it works but Stiles and Roy get along really well and neither of them seem to be overly territorial of Thea around each other. That’s always nice because saving the city is hard enough without having to deal with Thea’s boys between board meetings and torture sessions unscheduled, unwelcome visits from Isabel Rochev.
In a strange way, Thea’s whole thing about Roy actually makes kind of sense when Oliver thinks about Stiles’ background. His mother died when he was nine of some kind of dementia type sickness. Felicity had teared up when she had read it after hacking into the Beacon Hills Hospital records. Oliver couldn’t imagine watching his mother waste away and die with hardly any memory of him and he was almost thirty. Stiles had gone through that when he was nine. The whole revelation had earned him the silent treatment from Felicity for a week and her automatic approval of Stiles. It had also explained why Thea couldn’t leave Roy alone either when they’d first met- he wasn’t the first broken boy she’d come across.
So as far as hormonal train wrecks disguised as teenage boys go, Stiles isn’t terrible. He’s a little too smart and it puts Oliver on edge but he grudgingly trusts the boy with his sister’s life. Thea hasn’t made the best decisions but then again neither has Oliver. Stiles is one of her better choices, just like Felicity is one of his. The best part is that neither Stiles or Roy have a passport, so he doesn’t have to worry about his sister jetting off to some foreign country and drunkenly marrying them both in a legal polyamorous wedding. Because there is only so much he can deal with, even if he is Oliver Queen.