⋇⋆✦⋆⋇ losers club preferences⋇⋆✦⋆⋇

•Your First Date•

Bill Denbrough

When? Two months after you started tutoring Georgie. You became friends quickly, and both developed crushes on each other, but his low self esteem stopped him from asking. You eventually asked, and he was thrilled.
What happened? You two went to the quarry to stargaze together, and he brought you chocolate and blankets. You ended up cuddling and chatting for hours. It was one of the best dates of your life, which wasn't surprising because even as a young teenager, Bill was romantic.

Richie Tozier

When? At first, he asked you two weeks after you met. You didn't feel the same way. But, he was persistent, and another month later, you agreed (rather reluctantly).
What happened? You had grown to like him a little bit, though he wasn't romantic in the slightest. He took you to the quarry with the intention of skinny dipping, but you refused. You dipped your feet in, he went in anyway (in his underwear, don't worry). He forgot a towel, so he insisted you cuddle him until he was dry. You agreed. He liked the fact you were touching his almost-naked body. You stopped hugging him when he tried to motorboat you. But, you still had a good time and came out actually liking Richie more than you thought you ever could.

Stanley Uris

When? About a month after you met. You had started birdwatching with him, and he started watching the sunset with you. You spent this time with each other almost every day, and you two got really close. He was the one who asked. It was unexpected, and you didn't know he felt that way. You didn't really like him back (yet), but decided to give him a chance.
What happened? He took you to the cinema, and you watched a horror movie together. He chose a scary movie with the intention of you getting scared and coming to him for safety, but it happened the other way around. You let him eat all of the popcorn. By the end of the movie, you could see yourself dating Stan.

Eddie Kaspbrak

When? Only a week after you met (Richie was very surprised that Eddie had a date but he didn't) you asked Eddie out. You knew he never would because his mom didn't let him date, and he was too scared anyway. He shook his head violently when you first asked, and you had to calm him down and tell him his mom didn't have to know. After a lot of convincing, he agreed to go. He really liked you, after all.
What happened? You went out for ice cream, and bought a huge one to share. Eddie refused to eat any at first, because of all the 'germs' but once you tempted him with New York cheesecake ice cream he gave in. You two went to the park to try and finish the ice cream, but only ended up finishing 2/3 of it. He walked you home, and you tried to kiss him. It did not go over well with him. Still, it was a good date.

Beverly Marsh

When? You two had to hide in the bathroom from Greta for a long time, and ended up connecting really well. She asked you out that day. You said yes, of course.
What happened? You two knew that this conservative town would probably not approve of two girls together (except maybe Richie, who would ask to join in with your sex), so you guys decided on a secluded spot in the woods to have a picnic. She snuck some of her dad's wine, but it turns out neither of you liked it very much. You spent the rest of the date chatting about anything you could think of, until you couldn't help but kiss her. And, it did go over well (spoiler alert).

Ben Hanscom

When? You two often saw each other at the library, and noticed you had a similar taste in literature. He asked you out 4 months after knowing you, as he was really nervous.
What happened? He took you to a carnival that was nearby, and bought you lots of cotton candy and popcorn. You two went on all of the rides together, and finished with the Ferris wheel. And, as cliché as it is, you guys kissed on top of the Ferris wheel. Still, it was a magical experience.

Mike Hanlon

When? It took you guys a long time to acknowledge your feelings, and even build a relationship at all. You eventually burst and asked him 7 months after meeting him. He was in shock, and rejected you because he knew what everyone would say. But, when he saw it made you sad, he agreed. After all, he did feel the same way about you.
What happened? He took you to a deserted spot on his farm, and you two toasted marshmallows on the camp fire. He ended up giving you his jacket when you got cold, and you two huddled together next to the fire until the early morning.