OP here, Thanks for all of the feedback. Right now we are long distance so that is part of why we haven't just gone for it -- and life in general has gotten in the way. I am considering some major life changes so I want to explore all of my options -- including the possibility of trying to make a go with him.

Anonymous wrote:Completely fair game.

I won't pursue someone's ex if it is recent, if that person really hurt my friend, if my friend has never moved on from that person, or if the person has minor children with my friend. (actual friend, not acquaintance.) But someone's long-ago ex, who didn't screw friend over, who doesn't have kids with friend, and who seems to have little current ties with friend? Absolutely.

Agree with this.

For what it's worth, Im with a friend's ex of decades past. It was very random that we connected, we didn't seek one another out. They had a very casual relationship with no hurt feelings. It was awkward to tell her when we ran into her, but now I think she digs it. We've all remained friends. If there had been hurt feelings, pining by either, or he'd caused her emotional pain long ago I'd have not given him the time of day.

Completely fair game.

I won't pursue someone's ex if it is recent, if that person really hurt my friend, if my friend has never moved on from that person, or if the person has minor children with my friend. (actual friend, not acquaintance.) But someone's long-ago ex, who didn't screw friend over, who doesn't have kids with friend, and who seems to have little current ties with friend? Absolutely.

Anonymous wrote:Go for it, OP! And report back to us!

Yes! Let us know!

Go for it, OP! And report back to us!

Fair game, play ball.

Anonymous wrote:what are you waiting for

What is HE waiting for? He's had this supposed attraction for decades but hasn't acted on it? That's lame.

what are you waiting for

Twenty years ago? No longer friends with the friend? They have no lasting ties to each other? Go for it!

My first thought when I saw the title was "if you have to ask". I expected some really shady scenario. When I read they dated 2 decades ago, you guys were on the up and up, and person is no longer your friend I would say he is fair game. Awkward is if they were married, engaged, lived together, have a child together or if you regularly are in the same circle (socially or professionally) and they dated a long time/she is still single. Since none of those things are true, he is fair game.

Plus, who the f* cares if it is "tacky" ... you'd rather worry about if it is tacky or not and possibly waste the opportunity to be with this very awesome person??

THAT, dear, is just stupid.

And you aren't even friends with this other person? Please. Jump him. Just tell him.

Absolutely not. I'm 31 and there are guys I dated casually in my early to mid-twenties that I'd be happy to see my friends date (nice guys, just not for me). As long as they weren't engaged or living together I can't imagine your friend would care at all! Especially as you're not even friends anymore.

You're fine. I'd question the sanity of anyone who cared what happened 20 years ago. Plus, assuming you are 40 and under, this happened when they were quite young

I met a guy who dated a friend of mine (no longer friends with that person) over 20 years ago. Over the years we have stayed in touch. There has always been a mutual attraction between us, but since he was dating my friend at the time we kept things on the up and up. Every few years or so he will hint around that he is interested, but he won't just outright say it. I think we both feel awkward about the fact that he used to date my former friend. I guess the adult thing to do would be to have an open conversation about it, but would it be frowned up if I were to pursue a relationship with this man? More than two decades have passed and the other woman is married to someone else, but would it still be tacky?