I can see some potential in it (both are very smart, she could help him realise what an a-hole he was etc.) but overall, it's not for me. They'd have a very... loud relationship with both being extremely stubborn and prone to fight anyone with a different opinion, his parents would stress a lot and even though I'm all for redemption and forgiving bullies when they really changed, he was super duper shitty and this would always be somewhere in her head, and in his as well. I also don't think he'd be mature enough to actually letting his upbringing aside, so....
