bill:
who you're dating: patrick hockstetter
you were walking out of school on your last day when you saw your boyfriend and his friends bullying four boys known as "The Losers Club". you hated when they bullied them because the boys were actually really sweet. you walked over there. "patrick." you said. he looked up from kneeling over stanley. "hey babe." he smirked as he walked over and planted a wet kiss on your lips. "you know i hate when you do this..." you whispered, grabbing his hand. "come on, we're just having a little fun. speaking of fun, i'm still coming over tonight, yeah?" he smirked. you nodded. "yeah, sure." you said. he kissed your forehead. henry licked his hand and touched bill's face before walking away and laughing with his friends. "ugh, gross henry!" you yelled as the boys walked away. you grabbed your jacket and wiped bill's face. "i'm sorry about them." you said. "w-why is someone like you with someone like p-p-patrick hockstetter?" bill asked. "what do you mean?" you asked, putting your jacket away again. "you're so b-beautiful, kind, s-s-sm-smart, and he's, well, the o-opposite." he said. you giggled. "there are some things you just don't understand, bill." you said. "m-maybe, but i understand i could treat you s-so much better." he said. you blushed and kissed his cheek. "you're a sweet boy, bill denbrough. i'll see you around." you said as you walked away.
richie:
who you're dating: henry bowers
you were walking to your boyfriends house when you heard richie tozier riding his back behind you. "hey, y/n! wait up!" he called. you rolled your eyes and turned around. "what do you want, trashmouth?" you asked. "ouch,
now you're calling me that too?" he said. "what do you want?" you repeated. "i'm busy." "i want you to break up with bowers and go out with a real man." you laughed. "yeah? like who? you?" you asked. "well if you insist." he smirks. you rolled your eyes again and turned to keep walking. "no wait y/n, seriously." he said. you turned around. "what!?" you said. he sat and looked at you for a minute. "has bowers ever told you how beautiful you are?" he asked. "...no." you said. "no? how about how amazing you are? smart? funny? anything?" he asked. you bit your lip and shook your head. he was off his bike at this point, and was slowly lessening the distance between the two of you. "if you were mine, i would tell you that every single day." he whispered. your breathing was increasing now. "richie i have to go okay?" you said. "okay. just remember what i said. think about it." he said before getting on his bike again and riding away.
eddie:
who you're dating: richie tozier
(eddies POV oooh plot twist)
eddie sat alone and watched as you sat with his best friend and laughed and talked. he felt his heart break as you looked into richie's eyes instead of his own. you held richie's hand, talked to richie on the phone before you went to bed, thought about richie when you woke up, got ready every day to impress richie. he wondered what would happen if you knew that you were on his mind 24/7.
he kind of knew it wouldn't change anything, but he was still hopeful. (lol me)
his heart began to race as you turned to look at him. you waved and he felt his face hit up as he raised his hand. you were quickly distracted though, giggling uncontrollably while richie kissed your neck and jaw. he rolled his eyes and sighed as he looked away, knowing he could treat you so much better than richie could. and everyone knew it but you.
stanley:
who you're dating: bill denbrough
you were with stanley trying to plan something to do for bill's birthday. "i don't know what to do, im an awful girlfriend." you said. "no you're not y/n. bill's lucky to have you. and he knows it. everyone does." stanley said. you smiled. "thanks stan." you said. he smiled too. "hey uh, let's talk about something else for a second, like what you're gonna do for my birthday?" he said. you laughed. "okay stanley, what would you like from me for your birthday?" you asked, adjusting yourself to face him. "i want you to leave bill and be with me." he said. your smile dropped. "you...what?" you asked. "i want you to be with me, y/n." he repeated. "bill is your best friend." you whispered. "and he doesn't love you like i do." he whispered back. he reached up to touch your face but you backed away. "stanley...no. i love bill." you said. "and i love you. he doesn't. he can't. after what happened with georgie you really think being with him is a good idea?" he asked. "after what happened with georgie you really think leaving him for his best friend is a better one?" you asked, backing away. "y/n..." he mumbled. he grabbed your hands. "please." he whispered.
"wh-wh-what the f-fuck is going o-on?" you heard. you quickly moved away. "billy..." you said. "are you g-guys serious?" he asked. "bill it's not what it looks like okay? stop. let me explain." you said quickly. "n-no. don't." he looked at stanley. "you w-were s-s-supposed to be my b-best friend." he said. he turned and walked out. "i d-don't want to talk to either of y-you." you watched as bill walked away before turning to stanley. "nice going uris. thanks." you spat as you turned to leave.
