Oh wow. There's so many cliches in here it's a wonder the story doesn't just explode.
- Loser/loner protag batting way out of his league? check
- Turns out the girl might secretly actually like him more than she lets on? check
- loner protag might actually not be a loser, he just doesn't talk about his past for vague, mostly-not-discussed reasons? check
- overly pushy, sexually harassing friend of the girl? check
- She's also a gal even though the lead girl is all prim and proper? check
- secondary male character who's handsome and extroverted and on reasonably friendly terms with the protag even though everything else about the series is so incredibly class-conscious that you'd think the two should never interact? check
- Protag is insecure to the point that it's a wonder he can ever interact with anyone? check
Seriously at this point all that's missing is the jerk jock who shows up to steal the lead girl while bullying the protagonist around and the stuffy glasses & braids "plain girl" student council rep who reams them out for acting like a couple in public even when they're really not doing that much (and who potentially has a crush on the protag because he was nice to her once and they live in a world where an attractive girl in braids and glasses is suddenly rendered horrifically unattractive even if you discount fetishists)