Human AU where English teacher Derek’s overbearing sisters make him a Tinder profile and he matches with Deputy Stiles Stilinski.
The first date is definitely as awkward as expected.
The second goes a lot better because Stiles tells Derek about his partner (he’s in the K9 unit) and Derek talks to Stiles about his favorite book (To Kill a Mockingbird which was also Stiles’ mom’s favorite)
On the third date they have to leave dinner early to go to Derek’s apartment, they don’t even make it to the bed for round one.
The 7th date is a double date with Stiles’ best friend. When he asks how they met they tell him it was at Starbucks because neither wants to admit they found each other on Tinder. (Years later they admit it because it’s a funny story and Scott get’s mad because he talked about their coffee shop meet-cute in his best man’s speech at the wedding).
Date 22 wasn’t really a date so much as Stiles meeting the Hale family for the first time. After dinner they decided that Cora and Stiles’ friend Lydia can never meet or else they might take over the world.
The 29th date starts with Derek scared for his life because Stiles’ dad had his gun on the table the entire meal and ends with John and Derek making plans to go fishing.
Number 86-101 happen on an epic road trip from Beacon Hills to New York City while Derek is on summer break. He made Stiles take a vacation because by then he’d been on the force for 5 years and only used 3 total vacation days and by then they’d been dating for 2 years, it was about time they took a trip.
On the 102 date Stiles propose in Central Park. Derek pretended he hated how cliche it is was but Stiles knows he not so secretly loves big romantic gestures.
After that Stiles mostly stops counting the dates, except for the big ones, like their wedding, their fifth anniversary, the day their daughter was born, the day their son was born, their tenth anniversary, and well, you get the picture