hale-of-stiles-heart:

This was such a fun prompt to work with, Hannah! Also on ao3!

Stiles had a less than amazing dating history. To be completely honest, it was actually rather horrible.

Since he had started college, no longer stuck in classes with the same people who had condemned him to being the weird nerdy kid who couldn’t shut up to save his life, Stiles had blossomed. He was more confident, more outgoing, more self-assured. He was less self-conscious, comfortable enough to voice his opinions and flaunt his interests without fear of being ridiculed.

His newfound confidence even translated to his more romantic endeavors. He was no longer petrified of rejection, learning to hope for the best instead of anticipating for the the absolute worst.

When he met someone he found attractive or interesting, instead of convincing himself that they were way out of his league, he would focus on all of the potential possibilities. He would contemplate how nice a potential relationship, all the fun new things he could experience.

But while he was living college life to the fullest, partying with his classmates every weekend and going out on dates with anyone who asked or whoever Erica set him up with, he learned a very harsh truth. He had a habit of going out with complete assholes.

First, there had been Rob, a guy from his AP History class who had dreams of becoming a pro baseball player. He had been a charmer, constantly flirting with Stiles in the days leading up to their first date, always greeting him in class with a smirk and a wink.

He was a nice enough guy, that Stiles could concede, but he was also kind of a dick. With a wandering eye to boot. Every time they went out, without fail, he would end up paying more attention to their waiter’s ass than Stiles’ stories.

Stiles had finally broken things off when he caught Rob red-handed, shamelessly ogling Boyd while he and Stiles were on a double date with Erica and Boyd. He had nearly emptied his illegally gotten beer over Rob’s head in the middle of the restaurant. It was only because he didn’t want to make a scene that he managed to refrain, though later Erica advised him that he really should have just done it anyway.

After Rob, Stiles started dating a girl that Erica set him up with, a pretty brunette from another college name Ashlee whose biggest pet peeve was when spelled her name wrong. As someone who could relate, his nickname Stiles only a necessity because his first name was a nightmare to spell or even simply pronounce for most English speakers, Stiles hit it off with her from the get-go.

She was a philosophy major, a big fan of the Hobbesian theory of government, and absolutely adored playing the new Fallout game. They went on several dates, mostly to parties where they both danced terribly and got shitfaced on cheap whiskey that someone had bought with their obviously fake ID.

She gave him his first handjob, in the Jeep in front of her dorm building while Stiles dropped her off from one of their dates. She had slipped her hand down his pants after dinner at a local diner as they clumsily kissed. He came in his pants after just a few light strokes, face flushing as he apologized for coming so fast, a jolt of embarrassment shooting through him.

She had shut him up with a kiss and promised that next time he could get her off, winking seductively as she climbed out of the Jeep to jog up the walk to her building. But Stiles never got the chance. He found out a few days later that she was seeing two other guys in addition to himself. He had ended things on the spot.

After taking a few weeks to get over Ashlee, he had gone out with a guy from his English 101 class, the one he had fantasized about sleeping with a few times. His name was Andrew, spelled the usual way, and he was very easily one of the most seductive people Stiles had ever met in his nineteen years of life, with his easy grins and gorgeous blue eyes.

They dated for a couple weeks, Stiles performing his first blow job on him in his dorm, relying on years of watching porn to influence his technique, moaning obnoxiously a few times the way he had seen in pornos too many times. Andrew seemed to appreciate it, fisting a hand in Stiles’ hair to buck up into his mouth as he grunted, loud and crude, before finally coming.

He got dumped the following day. Andrew had claimed he just wanted a quick fuck, not some clingy boyfriend. Stiles had been pissed, drowning his woes in a bottle of booze and flooding the pack group chat with rants about how much of a jackass Andrew was.

It all dissolved into a series of half-assed dates after that, Stiles no longer caring enough to remember all of their names. Almost all of them turned out to be jerks in the end, anyway.

But there was a silver lining in the midst of all his dating sorrows. Derek.

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