First date headcanons (Losers Club) Pt.1

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Bill Denbrough

- He's super stressed out about everything, and Richie's only making it worse.

- Yeah Bill!! My buddy's finally getting laid!!

- Sh-sh-shut up Richie!!

- Doesn't know what to wear, how to act, or where to go (This poor bean needs some help)

-Thank god for Miss Beverly Marsh who saves the day.

-Relax, its going to fine. Just be you. (MOLLY RINGWALD JR.)

- A little insecure about his stutter, but you love it.

-Would probably do something like a picnic on top of the big cliff at the quarry, and then swimming.

- LOTS of blushing when you're just in your underwear ;)

- All in all it was a pretty great date, and you'd be seeing him again very soon❤️

Stanley Uris

- Seems chill about it but is internally dying

-He hasn't really been on a serious date and is highkey worried he'd screw something up with you

- Would be insecure about his religion, but knows you're not one to judge so he's cool on that

- The trashmouth would give some pretty trash dating advice

- You gotta compliement the pretty lady!

- Wow Richie that's actually -

- Tell her she has a nice rack! Or ass!

- Seriously? (-_-)

- He'd probably wanna do something simple, like hiking through the barrens to go bird watching

- Stan would fidget alot since you make him nervous (aww)

- After gaining some courage he'd reach out to hold your hand as you walk

- You guys didn't let go until he spotted a rare bird and raced off to follow it. You nearly fell into the pond.

- " (Y/N) !!! LOOK AT THAT BEAUTIFUL BIRD!!!

- It was an adorable date and you went on many more after that.

- And when the nature unit came in science class, guess which kids aced all the quizzes and knew every damn bird species??💗

Eddie Kaspbrak

- One word..... RAMBLING.

- Oh my god guys I'm sooo nervous like you don't even know! What if she hates me or the date? Or even worse she doesn't like the fact that I carry around TWO fanny packs! Oh good lord  I hope (y/n) isn't irritated when I take too many whiffs from my inhaler! This is crazy why did I agree to this I should have just told her I can't date because I could possibly get sick from all the physical contact that comes with a relationship!

- SHUT UP EDDIE! - The rest of the Losers Club

- Richie would DEFINITELY try to put him in one of his stupid Hawaiian print shirts

-  Eww no I can't wear that! It probably hasn't been washed in weeks! And I don't wanna smell like you!

- Bill would probably be telling Eddie to take deep breaths and calm down

- Stan the man would be rolling his eyes at all the arguing between Richie and Eddie

- Would take you for ice cream then bring you along to the drugstore to refill his meadication

- He was SUPER nervous so you held his hand to calm him down

- You ended up buying a fanny pack to wear too with an inhaler and extra meds for him (GOALS)

- When you tripped on the sidewalk and scraped your knee, he busted out his second fanny pack and immediately went Dr. K on you. (Richie's british accent not included)

- Two fanny packs Eds??

- Shut up (y/n)

- Don't worry, I think its pretty cute :)

- It was one of the best times of your life, and you couldn't wait to do it again💞

Richie Tozier

- He thinks he knows everything so he wasn't the least bit freaked out

- Beverly and Bill tried to talk to him about manners but he wasn't having it

- I don't need any advice from you guys! I'm Richie Tozier and I'm fucking awesome!

- LANGUAGE!! - The Losers Club

- Would wear the stupidest outfit because he thinks its "cool"

- But you loved it anyway :)

- The date would probably consist of a casual walk around town, and then him wanting to cause some sort of trouble

- Richie I don't think - 

- Hush (y/n), just follow my lead

- Let's just say he got you guys kicked out of the diner, the drive in theater, the drugstore, and pretty much every other place in town.

- So......... You wanna go spray paint on the alley wall?

- Considering we can't legally be anywhere else because of you, what the hell. Hand me a can.

- RICHIE TOZIER ♡ (Y/N) (L/N) 

- Aww you love me Rich! And now its forever engraved in the wall!

- You know it babe ;)

- LOTS of flirting and laughing

- Coming up with dumb nicknames for him that night like " Hozier" 

- When you got home, you were already ready to cause more mischief with that loser on another date💓

Ben Hascom

- A small and adorable bundle of nerves

- Insisted on meeting at your house just so you wouldn't see his NKOTB poster

- Kind of wanted to prepare on his own for the date, so the Losers were off somewhere else

- This small innocent child was so ashamed of his weight, but you asured him not to worry 

- He wrote you some of the cutest poetry and bought a boquet of flowers

- Would probably give himself a pep talk in the mirror

- Okay Ben, it's going to be fine. You're ready so just go out there and impress her. 

- You'd both spend the night at a diner talking and reading. He'd tell you about his old town and share some Derry history with you.

- History wasn't really your thing, but you loved the way his eyes lit up when he spoke. So you let him ramble on and on for a full 20 minutes.

- Sorry if I'm getting boring to you, (y/n).

- No no, go on! I love hearing you speak :)

- He'd be blushing hardcore everytime you flirted or complimented him

- It was honestly just a really cute and innocent date

- After he walked you home, Ben went to his room and jammed out to NKOTB music because he was just so happy.

- PLEASE DON'T GO GIRL!

- You really appreciated how sweet Ben was. You were so pumped for another diner date with him💟

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