Try Again…

I don’t think you keeping him at a distance was the only reason things didn’t work out before. If you’d since changed (assuming you’d become emotionally available, which you weren’t after the divorce), you were both single, and you’d previously been the *only* problem in the relationship, he’d have made a move already. The fact that he hasn’t and keeps at a distance from you in his own way shows there are issues on his end as well. Telling you he wants to try again and not taking any action to do so is absolutely meaningless and shows inconsistency on his part, which is a big red flag in a potential partner when you’re looking for a relationship and not a casual fling. This is probably a break up that should remain broken, but you’re still going to do what you’re going to do no matter what advice you get from strangers.

So if you want to try again with him, you’ll have to make the move because he’s already shown you he’s not going to do it. You’re worried and afraid about messing things up. That shouldn’t matter, though, because what is there to mess up? The friendship is already messed up right now because you want more and have an agenda to be romantic. The only way to fix that is to either get together and see how it goes, OR you tell him what you want, he says he just wants to stay friends, and then… nothing bad happens because you’re okay no matter what! You get over wanting more and after a bit of time go back to just seeing him as a friend again, and the once a year hangout friendship continues without the “what if?” tension.

Whatever you decide, don’t string yourself along (or let him string you along). Deciding to tell him what you want or deciding he’s too tepid and instead moving on to meet new men who actually know what they want will feel better for you than staying in this limbo.