Ask game fic premise: fake dating to qualify some sort of benefit (reduced gym Costco membership, etc.)
Oh yeah, I would totally write that. Bitty can't afford his own Costco membership, and they've started cracking down on people using other people's cards (they really have), so what is he supposed to do but find a way to get on his rich best friend's?
And that gets him on a few mailing lists as "Mr. Eric Zimmermann," which he feels some kind of way about but isn't going to say anything. And Jack has the high-end membership, too, so now Bitty is getting ads for housewares he will never afford. They go to Jack, because it's his address on the account, but he saves them in case Bitty is interested and Bitty thinks it's very sweet.
"Jack, I can't afford a single thing in here anyhow."
"I could buy it for you if you want."
Bitty: *dies*
Then Jack gets an invitation to, idk, something more exclusive than Costco. *waves hands vaguely* Some rich-people thing that includes exclusive events at all of Providence's best restaurants, members-only workshops with those restaurants' chefs and pastry chefs, that kind of thing.
"Bittle, I'll buy you a membership if you want. It's fine, you know it's not a big deal."
"Jack, the invitation is for you, not your random college buddy you're vouching for. See, it says right here, only the invitee can apply for membership, and once they're accepted they can add one significant other to their membership."
"Oh, so it's like the Costco thing. That's fine."
"It is not! Like! The Costco thing!"
And, y'know, things snowball from there.