My mom is currently dating a high school boyfriend she ran into at her 50th reunion a couple of years ago. They're not madly in love and she'll never remarry, but they're having fun together. Like the others mentioned, what have you got to lose?

Please go for it. I think there are many of us who wonder "what if" when it comes to first/lost loves -- but we are now in decent marriages, have children, and cannot simply ruin our spouse/kids lives by taking a chance on rekindling an old flame. It would hurt too many people.

On the other hand, you have nothing to lose whatsoever. I highly recommend you are totally honest with him. Ask him out to lunch or dinner. Tell him how much you regret breaking up, tell him that seeing him brought back so many memories, and tell him all the good stuff you told us. See what happens. If he is in another relationship or is not interested now, then at least you tried. You should never live with regret.

Tell us what happens!

OP, the ball is in your court. Since you dumped him, he will protect himself the way he's always done, by trying not to think about you. If you've changed your mind, it's up to you to take the initiative.

I say go for it. MIL went out with her ex of a similar era for nearly 10 years (she was widowed, he was divorced) and while it eventually ended because he didn't want a commitment (then, now, to his ex-wife) it was a positive thing for her. As others have said, the people who know you when you're young are close to you in a way that others just aren't later in life, in my experience. So there's an easy intimacy that is very comfortable, nothing wrong with that.

Life is short and you will never know what may have been if you don't try. Go for it. The worst that will happen is he will say, "No thanks."