So I had an idea with two pairings because it's always fun to play a more submissive role as well as a more dominant one.

Pairing(s): Gangster x Former Victim, Book Worm x Party Animal

Idea: So fluffiness abounds in the beginning, because I just like stuff like that. If you prefer darker themes, I'm all about them too so throw as many suggestions/plot twists to me as you like! I gobble up drama and angst. I'll refer to Gangster as G, and so on and so forth.

So G has had a massive crush on RJ for a while now, and after being teased by his friend P to nut up and ask him out, he does... And RJ says yes! Though with one condition... Considering G's violent reputation, RJ will only go out with him if he finds a date for BW (whom RJ has been trying to get to be social for months) for a group date, so G pesters P until he finally agrees to go along with it... Surprise, surprise! P and BW really hit it off, which shocked even them!

Had a few headcanons for these characters, and images pre-picked since they're what inspired me.

G I picture has having a very violent temper and alpha male personality, bad reputation around their school as a troublemaker. Classic 'bad boy', smokes, does drugs, skips school, has sex, just the guy that no parent wants their son or daughter to date. Has trouble getting a date because of his rep, and whoever he gets interested in usually gets harassed by his rivals on the streets. He's had a crush on RJ since he turned his life around and stood up for himself, and G admires that.
RJ I picture as being a former bullying victim and crybaby, though as he grew older his military father got him into martial arts and weapons so he ended up breaking out of his shell and being pretty badass himself, though he tends to hang out with nerds/bully victims since he can't stand bullies or the 'popular' clique at all.
P I picture as being a sort of gentle giant in a sense, though people tend to stay out of his way when he does get angry. Isn't as violent as G but they've been best friends for a long time because they both party and skip class all the time. Tends to have problems getting a date because he hangs out with gangsters and his hair covering his face makes him look like a thug. Has a part-time job as a fancy pants legal intern.
BW I picture as being anti-social to an insane degree. He doesn't like to talk to anyone at school besides RJ, and that's only because RJ has stood up for him from bullies. Tends to be rude and obnoxious to others, but only because he doesn't like to let people get close to him. He suffers from a disorder that prevents him from seeing/recognizing faces, so he has trouble dating because he can never recognize his crush from afar and always ends up offending them. Unknown to everyone but RJ, he has a bit of an alter ego... At school he's a nerdy guy with shaggy hair and glasses, but outside of school he sports several piercings, tattoos, and wears contacts... He's like a completely different person! Has never once attended gym class, coming up with god awful excuses to weasel out of it.

Pics

G (Secret softie for animals >.>)

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RJ (One being when RJ was bullied)

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P (Some with BW)

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BW (Gifs for his split-ego-ness, and one of his horrible excuses to skip gym lol)

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If interested, send me PM because I'm way more likely to check that than the forums!