richie

-he does the typical "who ever loses the game has to do what the winner says" thing
-you win, and he has to go on a date with you
-he's not complaining
-asks you out while on the date

bill

-he asks you out after school
-he gets really nervous cause he can see the others watching
-you hug him and peck his cheek
-this boi is blushing like crazy

eddie

-you walked home together
-on his front porch, you asked him
-real awkward
-but he's super happy and excited

stan

-you give him a note that tells him to go to the quarry
-you're waiting for him awkwardly
-when you ask him he dies on the spot
-many hugs much adorable

beverly

-in your bedroom
-she had come over to escape her dad
-"hey, (y/n). wanna go out?"
-"yeah, that'd be nice."