It oneshots

How he would ask you out (preference)

Bill-
-stutter x100
-would have to practice it before
-have Richie help him
"Just use one of my pick up lines girls love them!!!!"
"H-hey are you a b-b-banana because I wanna peel y-your clothes of and E-eat... RICHIE NO"
-Richie would dress up like you
"I was w-wondering if you m-mabye wanna g-go out"
"With Richie of course"
"R-RICHIE THAT NO H-HELP"
-would just give up and strait up ask
"I w-wanna go o-on a date with y-you"
-but then he would regret that
"W-wait n-n-no I'm s-s-s-sorry y-y-you don't h-h-have t-t-t-to I w-was j-j-j-joking h-haha o-o-oh m-my g-g-g-g-g-god I-I-I"
"Yes bill I'll go out with you"

Stanley-
-walks over confident as fuck
"Hello"
-you start to laugh because it's awkward
-now he's scared asf
"U-uh"
"Wouldyoumabyewanttogooutonadate"
"Stan-"
-walks away
-you have to fkn drag his ass back
"Yes I will"
-kissessssssssss

-Eddie
-no way
-eddies not asking you out
-he'll try but he can't
-will try Richie's pick up lines
-will get them messed up
"Did it hurt when you fell from Tennessee cause your the only Angel I see"
-Richie would be watching and start laughing his ass off
"What?"
-Richie will fall out of the tree he was watching y'all in and ask for him
"He wants to go out with you"
-Eddie will start yelling at Richie
-you have to shut him up by saying yes
"Yes Ed's I will go out with you"

Ben-
-will write a poem
-he would give it to you personally and run, as fast as he can
-you would read it and blush asf cause he's a sweetie
-takes hours to find him
-end up finding him in the library basement
"So you still wanna go out"
-He would be stuttering alottttttt but blush and nod his head slowly

Mike-
-confidant mfr
"Wanna go out?"
-randomly when y'all are hanging out
-you obviously say yes
-instantly puts his arm around you
-y'all have the date then and there

Beverly-
-scared bc she doesn't know if you like girls
-also confident in a way?
"Hey y/n do you think she's pretty"
-points to random girls
"Uh yeah I guess but your prettier"
-she blushes mad
"Wanna go out then?"
-starts to walk away but you grab her arm
-YOU KISS HERRRR
"Does that answer your question?"
-she smirks
-kisses you again
"Does that answer yours?"

Richie-
-this mfr
-will call you to hang out, as if it's not a date
"Wanna go to the arcade?"
-y'all meet there and play games n shit
"Hey this was a really nice date"
-you blush like crazy
"Richie-"
-kisses ur cheek
-pack ur bags ur moving to blush town
"I-I uhh"
"Bill? Did I just ask bill on a date?"
- more blushing
"N-no"
"Girlfriend?"
-girl ur cheeks are as red as bevs sink
-you catch on
"Boyfriend?"
-now he's the one blushing
-y'all just end up dating after that