Dear Meredith,

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 rollercoaster of his own, post-divorce. Been there, have a lot of empathy for the guy.

Fast-forward another six months to today. 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 email, 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 cancelled with a vague excuse and has not been in touch since. This time he left it with a “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 … he 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?

– Fooled Me Twice