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➙When they first ask you out

(This plays like when they're all living in Hawkins and you're already friends with them!)

Mike
Really nervous about making this kind of approach
"Hey, um, I was wondering if you'd like to... You know... Go out with me?"
You nod, making him smile widely
"That's amazing! Thank you so much!"

Will
Shy shy shy!!
Would need convincing from his friends
He can't even look at you because he's scared that you'll say no <//3
Fiddling around with his sleeves
"Hi, so..."
You look at him expectantly
"D-Do you want to go out with me?"
OFC YOU ACCEPT
"Sure!"
And you SMILEE
And he's just in awe

Dustin
"Hey!"
He does that little smile and it warms your heart SO MUCHHH
"Do you want to go out with me? It's okay if you don't want to, I just thought you were really cool"
"Of course! When's the date?"
HE GOES RED

Lucas
Lucas is confident
"Hey, would you want to go out with me? I know this super cool place we could visit, it's on me"
YOU AGREE OF COURSE!!
And it just relieves him too because he wasn't sure what you were going to say
It worked out great!!

Eleven
Would be way to shy to approach you on her own
Has to be pulled along by Max
"Hey, so El wanted to ask you out on a date! What do you say?"
You see her looking at the ground kicking random stones which you thought was adorable
"Sure! I look forward to seeing you, El!"
She blushes, smiles and nods :))

Max
She was unsure at first but she wanted to try!
"Hey, I was wondering if you'd like to go out with me? You're like, really cool."
She's a bit awkward
"Of course, when do you want to meet up?"
She's surprised that you agreed to be honest
"Anytime you want!"

Steve
Con
Fi
Dent
(We remember scoops ahoy when he introduced himself to the girls, only that you knew him already)
"Hey pretty, do you want to go out with me?"
YOU'RE BLUSHING
"Y-Yeah, sure! Is there a specific time?"
"Whenever you'd like ;)"
He may act like he knew you were going to say yes, but he's still really relieved that you did :))

Eddie
Also confident!!
"Sooo there you are, beautiful."
"I was asking myself if you would agree if I invited you out on a date?"
Really flirty and he does it so well!!
"I-"
"If you don't want to that's okay too, I just thought you were really pretty and I always wanted to ask you that question."
"You didn't let me finish!"
You both giggle around for a bit
"I wanna go out with you!"
He puts his fist up in success
"Yesss!!"

Gareth
Also a bit unsure
But he didn't want to waste his chance
Shyer than he expected, since his attitude is normally um, yk.
"H-Hey."
He's like standing there playing with his hands trying to figure out what to say
"Yes?", you say with a gentle smile on your face
"U-Um"
He sighs
"I'm sorry. I wanted to know if you would like to go out on a date with me? I completely understand if you don't want to, I just didn't want to waste my chance."
"Gareth, finally you asked! Of course I'd like to!"
He's surprised
"O-Oh?"
"Yeah, I have been waiting for this!"
"Well, when do you want to meet?"
"How about right now?"