Breaking up sucks, but it hurts even more when you are breaking up for the right reason. Sometimes, no matter how hard you try and how much you truly do care, it doesn’t work. It doesn’t mean he didn’t care, and it doesn’t mean you didn’t make him happy- people have different fundamental views on how relationships work that are hard to change. It’s not “old school” or “high standards” that break a relationship- it’s treating your other how you want to be treated. The stress of law school doesn’t help in any relationship either. It’s okay to be sad- it was a fun run and you did truly care about him. But nothing is worth the stress, frustration, aggravation, and disappointment for those few minutes of happy that you get from your relationship. You can try only so many times until you just can’t anymore- it’s exhausting trying to fit a square peg in a round hole- it’s never going to fit.
You learn some, you love some, you lose some- but you will always be happier in the end.