27.[Headcanon 02]

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How they ask you out

Jaeden 

- Jaeden was one of the uhhh smoother boys when it came to asking you out 

-He even clued in your parents on the plan so it would go on without a hitch 

-He came to your front door + your parents made you go open it when he rang the doorbell 

-and this cutie was outside with your favorite flowers in hand

-"Hey (y/n), listen, I think you're a really beautiful person inside and out, and I wondering if you would go on a date with me?"

-You literally wanna squeal because AW 

-obviously you say yes to him 

-You give him a hug and he gives you the flowers and that's that 

-After he left, you spent the rest of the night texting him until you fell asleep 

Finn

-So we all know Finn is a huge dork 

-And he's also musical 

-so naturally, he used these two things to his advantage when asking you out

- He asked you over to his house, and told you to meet him in his backyard

-where he was set up with his guitar

-and proceeded to serenade you with a song he wrote for you 

-he asked you out after it was over 

-ngl you cried a little bit 

-of course you said yes 

Wyatt 

-Wyatt is the cutest part 9567362

-He wanted the way he asked you out to be special 

-he was thinking about it for weeks 

-he got his friends to help him out

-he made a little basket full of your favorite snacks and candies

-and he made a little card with quotes from your favorite books

-and he gave it to you after school one day 

-you had the biggest smile on your face and it didn't go away for days after 

Jack 

-Jack... he is not as thoughtful as the other guys when it comes to this 

-In fact, asking you out was kind a spur of the moment thing 

-the two of you were hanging out alone one day, binging the Sharknado movies and making fun of them 

-and you had him nearly crying with laughter as you roasted the movie nonstop 

-when he finally calmed down enough, he just sat there looking at you 

- "Will you go on a date with me?"

-that was it. simple as that

-you stared at him for a moment before obviously saying yes 

-both of you sitting a little closer for the rest of the movies

Chosen

-Chosen wanted to do it the classic way 

-he liked you for a while and had been trying to gain the courage to ask you 

-so when he finally did he was nervous as hell 

-he brought you roses like the adorable little gentleman he is 

-and the poor guy was stuttering the whole time 

-you giggled at his nervousness because how could he think you wouldn't say yes??

Bill 

-You had been Bill's support system for years 

-throughout grade school you defended him for his stuttering and were there for him through Georgie's death 

-Once things started getting better after summer

-Bill realized he loved you, and not in the friendly way 

-So one day, he asked you to hang out with him down at the quarry 

-and he just asked you, minimal stuttering and everything 

-You smiled at him, saying yes + kissing him on the cheek 

-He was blushing like a bright little tomato 

Richie

-Richie was struggling with how he wanted to ask you out for a while 

-You were the only one he toned down his vulgarity in front of

-and he wanted to get the point across that he could be a gentlemen if he wanted to 

-he kinda failed

-he asked you to get lunch with him at the diner one day 

-and as you're both sitting there, eating and talking 

-he just goes, "so, think I can consider this our first date?"

-You're silent for a minute because you didn't realize that he liked you like that 

-but you just went, "yeah I'd say so."

Stan 

-Stan does not have much experience with the ladies 

-The only thing he really knows is to treat them the exact opposite way Richie usually does 

-So he keeps that in mind when trying to ask you out

-One day, he invites you to do homework with him 

-Obviously, you happily oblige 

-While flipping through your textbook a little note falls out 

-you open it, and in Stan's distinct handwriting it says 'you're the peanut butter to my jelly. Go out with me? -Stan"

-You giggle, before telling him 'yes'

Eddie

-Eddie is so so so scared to ask you out 

-even thinking about it makes him have to use his aspirator

-he's been friends with you for a long time and is terrified of ruining it 

-Nonetheless, he knows he has to do it, just to see what you'll say 

-So one day as you're bike riding, he's trying to get up the courage to ask you 

-and he gets so nervous he starts having trouble breathing 

-You end up getting his aspirator for him and helping him calm down

-as soon as he catches his breath, he rushes out "(y/n), I really like you, will you please go out with me?"

-You say yes of course

Mike

-Mike actually didn't know you beforehand

-he was on one of his trips into town when he saw you for the first time 

-you know, you were casually looking drop dead gorgeous 

-and he walked his bike right over to you

-smooth as hell 

- "Hey, I couldn't help but realize how beautiful you are. Would you maybe want to go on a date with me?"

-you're blushing because it's so unexpected

-but you manage to squeak out a yes 

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