[Coldsaturn]

The angst <3 I love it so much.
And yes to everything. The only emergency exit is if the reincarnated MC is very different from both her Academy version and her High School version. Very similar (if not the same) face, but personality wise she's so off that it feels like another person (which would open another can of worms). But if she's anywhere close to "familiar" then he's screwed. And it's also so bad because he wouldn't even be trying to recreate memories that already exist with her: back in high school he only had the time to fall in love before it was all over, so what was left behind was all the expectations, fantasies about the future, etc. Those are so idealistic that you'll never properly match them. Not with your actual first love. So it's a lose-lose situation where it will never be just right.