First with the dealbreakers in spirit of saving you time. I mostly do my roleplays on discord. It would be rather hard to convince me to do it on here but not impossible. And as a side note, i do not intend for this to turn mature.

I cannot get this thought out of my head, it's been several years since i first started to look for these kind of roleplays but here is the gist of it.

Artsy shy kid X Jock/Popular person.

Sure open to more depth and detail than that but that is the bases of it. The character i had in mind for this, and the setting in general. Would be of the shy kid. It would most likely happen in a slightly more upscale highschool or college (Highschool has uniforms so that's a point up for me, open for debate though). I really like the theme of societal expectation VS personal wants and needs, someone being made to fill a box they don't fit.

Personally i'd love to play the Artsy kid, the shy one in the back that doesn't make an effort to hang out with other people and isn't exactly the best in social situations. Send me a PM if this sort of thing interests you.