stiles has several bad (read: terrible) breakups back to back within the span of six months and declares loudly to the pack: "i'm giving up sex! and liquor! no good things come from being drunk or thinking with my dick - no more!"
the whole pack (everyone's alive because i said so) takes bets on how long it's going to last. most of them are sure stiles can't go more than 10 days without a drink; nor would he actually resist the temptations on Grindr and Tinder for more than 25 days. they know him and his (lovable) self-destructive tendencies far too well. derek is the only person who bets that stiles lasts longer than a month.
10 days pass. scott and kira live with stiles, so they would know - they say he's really kept it up. no booze. no random hookups. stiles goes to the gym, takes his meds, has even stopped watching as much reality TV. (although he still religiously watches that show about the island where the guys hunt for treasure, because he has to have some vices.)
lydia and isaac both bet that stiles would make it 20 days - so they're subtly inquiring about his social life, casually discussing new cocktail recipes, anything to chum the waters. but stiles doesn't take the bait, just happily reports back on how much easier things have gotten at his job, where colleagues seem more collaborative and his daily slog is less slog-like.
boyd and derek are the only ones left who can still win 25 days later. if stiles breaks before a month, boyd wins the pot. so our pal vernon boyd iii "accidentally" lets stiles catch him and erica fooling around in derek's living room on pack night. (they can tell he's aroused, but he just bitches about boundaries and locked doors and never pulls out his phone. shit, boyd thinks, did he delete those dating apps? that would be a problem.) and that same night erica makes blended strawberry margaritas, stiles' not-so-guilty pleasure. but he cheerily makes himself a "virgin" drink while cracking a joke about being as celibate as the mocktail - and boyd curses the fact that he put a fucking hundred dollars down. stupid derek's already a goddamn millionaire - the bastard.
and derek may be a smug bastard but he's gracious enough not to brag. a month passes. stiles remains unlaid and sober. so scott, the holder of the cash, passes the bounty off to derek, who grins silently at the cash as he counts it. scott wants to ask him how he knew stiles would actually keep his word for a whole month, when he's tried and failed to clean up his act in the past. but scott feels a little bad that he didn't believe in stiles (at least, that's what it looks like, he knows) so he doesn't push derek on anything, just pats his shoulder and asks him how he's going to spend the money.
"not sure yet," derek tells him with a shrug. "i have a couple ideas."
just because scott's a coward doesn't mean the rest of the pack are. so they're all together at the next pack night when jackson spills the beans about the bet and demands that derek tell everyone how he knew stiles would actually be able to stay away from casual sex and liquor for four whole weeks.
(stiles doesn't look surprised by the question, only amused, which should be everyone's first hint that something is off - stiles clearly knows about the bet, and he isn't yelling at them for doubting him.)
derek brushes off the question at first, but more of the pack members join in, demanding to know his thought process. so derek takes a sip of his drink and smirks in stiles' direction as he admits:
"i told him if he made it all month, i'd spend the money on a date with him."
"oh, shit," lydia laughs.
"goddamn," boyd mutters. "i lost that bet too."
"oh yeah," stiles says, grinning easily at derek, "they have a bet going on when we're gonna finally have sex. and i know who's gonna win."
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