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Is he behaving this way because of his recent divorce?

He reconnected ... and then didn’t

Love Letters

Love Letters

Q. Over two decades ago, a man I loved very much ended our relationship. I was pretty devastated at the time, but life carried on. I’ve always remembered him fondly.

Almost a year ago, this same man found me on a dating website and reached out to reconnect. When I responded, he immediately withdrew and confessed that he was recently divorced and wasn’t ready to date. He left the door open by saying, “Maybe someday down the road, when the timing is right.” Then he blocked me. I was kind of taken aback at how abruptly his tune changed, but I chalked it up to him likely being on an emotional roller coaster of his own, post-divorce. Been there, have a lot of empathy for the guy.


Fast-forward another six months. He reconnected again and asked me on a date. It felt like maybe I had been on his mind and he wanted to start fresh, so I said yes. We began to trade memories via e-mail, building a new rapport. It felt really nice to get to know him again. He did admit at one point that he was almost ready to “throw in the towel” because he didn’t want to start something he couldn’t finish, but also that new feelings had developed that he wanted to explore.

Then, the day before the date, he politely canceled with a vague excuse and has not been in touch since. This time he left it with “I hope we still are able to get together soon,” but it’s been a few weeks of silence. Clearly he had a change of heart about reconnecting and I’m fine with that; I mean, I don’t even really know him today. If this were any other first online date I’d recognize the hot-and-cold behavior for what it is and move along, but this man ... was once very significant to me, and the way he keeps reaching out only to disappear again is confusing. Any insight into this behavior, or advice on how to handle the situation if he reconnects for the third time?



A. If he reconnects for a third time, let him know you’re not interested and move on. If you’d prefer to block him now, go ahead.

I can’t tell you why he’s behaving this way with someone like you — after so much history — but you made the great point that you don’t know him anymore. Maybe this is what he’s like now. How nice to have that information up front!

I’ll tell you where he lost my support in this story: “Maybe someday down the road, when the timing is right.” And then here: “... he was almost ready to ‘throw in the towel’ because he didn’t want to start something he couldn’t finish.”

Those aren’t evil statements or anything, but he didn’t say, with empathy, “Hey, I’m not ready to start something new and important, and I don’t want to waste your time or stand in your way.” It also kind of sounds like he assumes you’d be into him, no matter what. Who’s to say you wouldn’t be the one throwing in the towel because of lack of interest? There’s a vibe here of him believing that he’d be the one letting you down in any scenario. Meanwhile, you might have had one in-person date and been all set to walk away forever.


Divorces can be complicated and confusing, and sometimes they require people to be self-centered about their lives, without bad intentions, as they make big changes. But he’s a grown-up and should respect your time. He was significant back then, but not now.



Who cares what his reasons are? He’s flaked out on you multiple times. Nobody needs that in their life. Take charge of the situation and block him.


Why not point blank ask this guy what is going on? Why is he going back and forth? Obviously it bothers you enough to write in here asking questions. If you’re afraid to rock the boat, take a look around. That boat hasn’t even sailed into port yet.


I think he is still married.


Send your own relationship and dating questions to loveletters@globe.com or fill out this form. Catch new episodes of Meredith Goldstein’s “Love Letters” podcast at loveletters.show or wherever you listen to podcasts. Column and comments are edited and reprinted from boston.com/loveletters.

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