It was a bet
Jackson was being an ass, again. He was being mean to Stiles and picking on him for not being good enough for lacrosse and never having a girlfriend. He kept telling Stiles that he’d never have a girlfriend, he’s not good enough and frankly, Stiles had had enough and said he could easily get a girlfriend if he tried which resulted in Jackson betting he couldn’t. Stiles realised he made a big mistake when Jackson chose the girl; you. You being the other Lydia. Before Allison, it was just you and Lydia as the popular girls, the two of you practically ran the school, and still do. With Allison dating Scott and Lydia claimed by Jackson himself, that left you. Jackson thought that it was an easy win but you thought Stiles’ awkward and shy behaviour when he tried to ask you out was just adorable and agreed to one date.
As you walked through the halls the day after your date, which wasn’t as bad as you expected- you actually liked his sarcasm, sass and joking around and thought he was adorable- you happened to overhear his conversation with Jackson. Neither of them knew you were there as you stayed hidden while listening in. ‘Guess you won the bet. She’s softer than Lydia, too nice.’ Jackson sounded a tad annoyed. ‘Here, $40.’ ‘Keep it. You made me ask a very nice person on a date who actually said yes, actually showed up and was good company and didn’t get annoyed at my sarcasm and laughed at my jokes. I should thank you, buddy.’ Stiles rambled on and you smiled to yourself that Stiles just turned down the bet and actually liked you. You were always in Lydia’s shadow. The other one. No one really knew you and you never really had a proper boyfriend that Lydia hadn’t forced at you. ‘Your loss. She probably won’t go out with you again though, she just said yes out of pity.’ Jackson was clearly trying to make himself feel better, personally, you didn’t like him. You just accepted him for Lydia’s sake. ‘Even if she doesn’t, I went on a date with a beautiful girl and had fun. Thanks.’ You heard Stiles starting to walk away from both you and Jackson.
When you saw Stiles alone at his locker later that day, you went for it. Mostly because you like him, but partly because you wanted it to be a big “fuck you” to Jackson. ‘Stiles. Hey. I had fun last night and wondered if you wanted to do it again.’ You were probably just as awkward as him, who stood in shock for at least 2 minutes. ‘What? Y-yeah. Sure. Of course. Really?’ You laughed, ‘really.’
Stiles had bet that Scott wouldn’t ask you out. You were new and had caught Scott’s eye, but he had just broken up with Allison Stiles felt he needed a distraction from Allison and bet him to ask you out. You had said yes and went to a party with him, yes, same as Allison. It was all fine, until Allison saw the two of you dancing and he freaked out. He had told you to stay there and went after her but after a while, he still hadn’t come back, so you went to find him and over heard him say, ‘Stiles bet me to go out with her because he said I needed to stop thinking about you but I can’t.’ You didn’t even bother to interrupt, or stay. You just left. Stiles had noticed you. You weren’t angry or anything like that, you were more fed up and a little amused. Scott had messaged you, once; “Stiles said you left. Sorry we bet on you, you’re actually really cool and both of would like to apologise and get to know you better. Talk tomorrow at school?’ You simply replied with “sure” before going to bed. The three of you talked the next day and all became really good friends, especially when you found out Scott was a were-wolf, which didn’t phase you as you already knew all of that stuff from family friends, you were just never involved before.
You were an omega. You had been walking through the woods of Beacon Hills. You had just arrived and were only passing through but you were attacked by another wolf. An alpha. An omega vs an alpha was basically suicide for an omega but you had no other choice. You were actually doing pretty well, all things considering, but you were getting increasingly weak and needed a long time to heal. Derek and Peter had also been in the woods when they heard the commotion and went to check it out to find you, covered in your own blood, fending off an alpha. Derek was pretty impressed by your skills and determination, but you weren’t going to last so he stepped in, Peter just watching because he ‘isn’t strong enough’. You blacked out from blood loss so didn’t get to see how it all turned out. You woke up in a loft. Derek’s loft, to be exact. He had helped you and cleaned you up while you were out. Peter had noticed Derek and teased him because he knew Derek liked you. Peter had bet that Derek wouldn’t tell you, in fact, he bet that Derek would have you out of there the second you woke up. It wasn’t a proper bet with money or anything, more of just teasing. But that teasing led to you staying, becoming part of the pack, helping get rid of the alphas and part of Derek’s life.
It was Erica. Isaac had liked you since before he became a were-wolf but was always too shy and scared of his father to talk to you. Erica found out almost immediately after they became wolves and bet him $20 to finally ask you out. You had also liked Isaac but the two of you never talked properly. You had overheard the whole ‘bet’ conversation consisting of Erica making it and Isaac at first not wanting to but agreed once she pushed. ‘Hey, y/n. I was wondering if you’d like to go on a date with me.’ He acted all “cool” wearing his leather jacket and everything. You liked the new confidence and the jacket but not so much the bit of jackass he had picked up. ‘When at least some of the old Isaac makes an appearance and this jackass phase leaves, ask me again.’ You got up from your seat in the library and left. He never won the bet, but after you were in the wrong place at the wrong time and found out about the supernatural and Isaac, he told you everything and some of the old Isaac came back and that date finally happened.
You actually knew before you started dating. You were popular in the school, Lydia level popular. You had heard the whole conversation between him and his friends and decided to have a little fun of your own. You would flirt with Jackson any chance you had and when he asked you out, you always said no. It got to a point where Jackson no longer cared about the bet and was just getting frustrated to why you were flirting and being nice to him but wouldn’t go out with him. This went on for a few months and you started toning down the flirting and being genuinely nice to him. Over the few months, Jackson had also learnt some things about you and got to know you. The two of you started to actually like each other and both forgot about the bet when you finally told each other and finally went on that date.
Aiden (not really a bet)
You were the chosen member of the Scooby gang. Ethan went for Danny and Aiden to you, Scott’s twin sister, by orders of Deucalion. At first, he was just someone to have fun with. You had broken up with your boyfriend due to the pack secrets that you couldn’t tell him, so you didn’t want a relationship. You then found out he was part of the alpha pack. Did that matter? Not to you. The two of you rarely actually talked and truthfully, the two of you felt free from the were-wolf shit when you had your fun together. However, your stupid heart got in the way and started to feel something towards him. The same for him to you. You knew that Aiden only spent his time with you because of Decalion’s orders, get close to the true alpha’s sister. This meant that you thought Aiden didn’t have any real feelings towards you. After the alpha pack was done with, he started to show he cared but you wanted him to show he cared for the pack as well as just you, but gave him a chance on that basis. He was proving himself and still had a way to go, but you knew he was trying. The two of you got closer and you were devastated when he died.