YOU asking THEM out.

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Billy Loomis- "Oh." Billy replies, but more of a relieved tone than a shocked one. It means for once, he isn't the one that had to ask you out first.  

"Of course, where and when?" He asks with a smirk, preferring to do whatever you like first before he feeds you all of his own desires in turn. It's a somewhat positive leftover from his manipulation trait.


Stu Macher- Obviously, his first reaction is to do that goofy grin of his before saying yes. If he really likes you, then his mind is no doubt planning of all the ways he's gonna use his parents' wealth to spoil you and show off. 

"Babe, name the time and place, I'm buying everything!" He tells you, boasting his money muscles hard. 


Mickey Altieri-  Will smile at you with a hint of respect that you asked him out first, since he was hoping you would because of all the flirting he did in hopes you would get the hint that he was serious. 

"Took you long enough to say that." He says before taking a big step of his own and planting his lips right on yours. "What are you thinking?" 


Nancy Loomis, because adult couples exist- This is me guessing that her and Hank's divorce was somewhere around the same timeframe as Maureen's murder. So, in my opinion, it'll take the full three years, two if you're lucky, for her to consider dating again. Most likely, it would be best to drop it on her calmly with the safest words possible. 

Once she gets the hint of what your proposing, she sits there surprised, before thinking hard. "I... I want to... but I still see my ex-husband in my head sometimes." She tells you honestly. "Give me some time, okay?"


Roman Bridger- Although a serial killer, Roman borrows some personality traits from his sister. By that, I mean if you ask him first, then he'll actually stutter for a bit in surprise before giving a genuine a smile that looks kinda like Sidney's. (Small difference is Roman will look even more shy because he tries too hard to hide it.)

"Of course, I'm actually free this Friday." He tells you in a excited voice. "No work, nothing, we'll have the entire day to ourselves. That sound good?"


Charlie Walker- He's a teenager who's practically convinced himself he won't score any action, despite having the courage to actually hint his feelings toward Kirby. He'll say yes in a heartbeat, willing to give the relationship a try. If he does like you, he won't know it yet because of the mentioned Kirby.

"Sure, I'll take whatever my lonely ass can get." Charlie replies with a shrug, chuckling. "Um.... what are you thinking?"


Jill Roberts- She smiles like a devil, one of the first moments you see her true colors. However, it's because she genuinely likes you back. Being a Psychopath doesn't mean love is out of her vocabulary, even though I'd still say be careful. After Trevor's betrayal, you always made sure she was okay and never tried pushing your relationship despite your feelings. It was something she started to suspect, and she admired it, which is funny coming from her.

"Of course, Y/N." Jill replies with a devilish, but genuine smile. "My mom will be out of the house for the night, if you want to stay there?" 


Piper Shaw- Honestly, Piper Shaw in her genuine form is most likely a Gale Weather variant. So the most likely scenario is that you drop this question outta nowhere while she's doing whatever she's 'busy' with. Thankfully, it'll work whenever and whatever. She freezes, takes three seconds to process what you just said, then gets herself together and gives her answer

"You know what? That sounds great." Piper tells you with a surprisingly genuine smile, much different than her business looking ones. "I'll text you the details later tonight." 


Jamal Elliot- Gonna give it to you straight, you better make sure your ready for other things other than a simple date. Because Jamal has the same kind of mindset as Billy, Stu, and Mickey, only that he'll make it much more obvious. 

"Sure thing, I know a couple places we can hang out at if you want." Jamal offers you with a small grin. "Or we can hang out at my place?" 


Beth- You'll actually see a surprised look from the goth as she realizes you're asking her out. She never thought anyone would... be the first to notice her. Like many of others, she gives you a genuine smile before answering.

"I'd like that." She replies, looking at you with a hint of lust in her eyes already. "I'd like that very much...."


Amber Freeman- Upon realizing you're asking her out, she loses her 'cool' persona and starts jumping around like a kid who's just won a bucket load of cotton candy. Part of her wanted to be the one to ask you out, but hearing this lets her know you already feel the same way, and it makes her giddy. 

"Yes! Yes! Yes! YES!" Amber exclaims, giving you a hug that's way too tight for your lungs to handle. It's almost like she just heard you propose instead of simply ask her on a date. "Just.... yes!"


Richie Kirsch- Will blink for a second in slight surprise, before giving you his cheeky smirk and giving you a quick yes. He's very glad that you asked him out first, because he it means he doesn't have to waste time scanning for clues that you feel the same.

"I would love to, Y/N." He tells you with a grin. "Choose whatever you want and we'll be there.... sorry, that sounded really lovey-dovey, didn't it?" 



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