This is something I think about a lot.
Part of me would love to go back and redo high school.or college and just be a better student, learn more, and flirt with girls more (although now that you mention it the age thing would make it weird, you're right). But I end up at the same conclusion - it wouldn't be worth not meeting and marrying my wife.
It'd be so difficult to meet her again (we met on Tinder) and to make it so she's interested in dating me. And then the relationship would be so one sided because I'd know every intimate detail of her past and she'd know nothing of mine.
So, I eventually come to the conclusion that nothing I could do in the past is worth risking her.
FYI for anyone not in the know, this is the Good Good Good Newspaper advertised by Hank Green
It only consists of "good" news and is very uplifting - generally every print edition features some kind of theme like "animals" or "medicine" or "art"
If you can afford to support, I think it's a great way to encourage more uplifting news in our world
https://www.goodgoodgood.co/goodnewspaper/subscribe