I know I jest about Ilya making Questionable Decisions(TM) by wearing a Boston Raiders shirt to meet Yuna "Biggest Metros Fan In the World" Hollander, but the more I think about it, the more it strikes me that it might be one of the smartest, subtlest character choices in the show for Ilya.
"That's not going to help," Shane tells him.
"Oh," says Ilya, deadpan. "They don't know I play for Boston?"
On the surface, it's funny. Haha, Ilya choosing the worst possible shirt to wear to meet his future in-laws. But underneath, it seems possible - even probable - that this was a calculated choice. Ilya, as we know, is a master of self-sabotage. He is also a big fan of cutting things off before they have a way of being taken away from him. At this point, his and Shane's relationship has just been outed to Shane's parents in one of the worst ways possible. There are obviously worse ways for it to have happened, but Shane is panicking, and Ilya knows he's panicking, and while Ilya may not show it externally, I would wager that he is almost certainly also panicking inside. Because he and Shane had just - literally just - agreed to try and make things work. While they've been hooking up for the better part of a decade, this new phase of their relationship is terrifyingly new and fragile.
It seems likely that while Shane had thrown on some random outfit and paced a hole in the floor before deciding to take himself outside to pace some more, Ilya, who had stayed behind to figure out his own outfit, had told himself that this was very likely the end of their nascent relationship. Or, at the very least, a big hurdle to overcome not even one day in. After all, as Ilya well knows, Shane's mother is Not going to be a fan of Ilya, not least because he is captain of a rival team, but also because he has garnered the reputation of being the "biggest asshole in the league". Nobody really likes him. Ilya is inured to this simple fact. Shane's parents - especially his hockey-loving mother - are not going to be any different.
And, so, Ilya, left alone to his devices and the demons in his mind, decides that he might as well lay it all out now and remind Shane's parents of exactly who he is. Yes, he's Ilya Rozanov, their son's apparent arch-rival since they were rookies, captain of the Boston Raiders, notorious playboy who has slept with who-knows-how-many women. Remind them of the worst parts of him, is Ilya's logic. Let this blow up now, while Ilya has only just gotten a taste of what he could have with Shane. Yes, it will probably destroy Ilya to lose this now, but he could maybe still put himself back together if it happens now, than if it were to happen further down the track, when he's let himself become too comfortable and secure in this thing with Shane. Because if he lost Shane then, Ilya would probably never recover.
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