Q. I was in a serious relationship while pursuing my master’s. As my program was coming to an end, I planned to move to where my girlfriend was at the time, as she was pursuing her own degree. But we had some big life talks and I ended up initiating a breakup because I felt like our end goals weren’t aligned, mainly with our interests and where we were going to live.
The breakup was terrible. I really cared about her, but I thought I belonged with someone much more “my type” on the surface. I ended up getting a good job in the place I said I didn’t want to be originally, and I’ve been able to make it work. I feel like my ideas of what I want have changed, too. I’ve tried dating; the success has been limited.
Fast-forward to a recent weekend, about a year and a half post-breakup. Old friends were in town and we all got together. It took a little bit to actually start talking with my ex at this event, but once we did, we talked the rest of the night. It was so nice having great conversations, the kind I’ve missed with any other potential partner. I also really admire what she’s become and I feel like she’s made very positive changes that I like more. I feel like I really miss her in my life and want to reconnect, but I’m not sure if it’s best or if she would like that.
I don’t know exactly what I would want from meeting back up, but I know I was so happy being together briefly the other night, and I want more of that. I have already messaged her and said it was really nice to see her, and that I would love to see her again. I think I did a good job of being very “no pressure” but who knows! And she said she would be up for getting a drink sometime. I could use some expert, unbiased guidance about proceeding.
P.S. — Love the podcast. I was late to the game but am working my way through them.
A. Thank you. Everyone, work your way through the Love Letters podcast, please.
My thoughts: You asked her out and she said yes. That’s great. Now, stay clear about your intentions, and ask her if she’s comfortable seeing where this goes.
Remember that you’re not auditioning her to be your partner again. If you want to compliment her life choices―how she’s changed — make sure it sounds like an observation, as opposed to patronizing approval.
Assume you’re starting a new chapter because the relationship — even as a friendship — can’t be like it was. Someone got hurt (I assume). There was grief and confusion — and probably, hopefully, some healing and forgiveness. Make no assumptions about what she wants now.
Also know that she’s not the answer to all dating problems. There are other people out there with whom you can connect. If you want to pursue her, it shouldn’t be because you believe she’s the only one.
Start from scratch, be grateful for her time, and stay honest.
“I love you, now change for me so that you deserve to be with me.” FRIARTUCK01
You’re comparing her with other women you meet, but the playing field isn’t level because you have a history with your ex. SUNALSORISES
Nobody’s asked her; she would be a fool to even consider it. CCBEACHCOMBER
I know few married couples, my wife and I most definitely included, that didn’t have a major breakup somewhere along the way. Worst case, she tells you she’s not interested, and you’re no worse off than you are right now. CHARCUTERIEBOARD
Find the new season of the Love Letters podcast at loveletters.show. Send your relationship quandaries and questions to email@example.com. Columns and responses are edited and reprinted from boston.com/loveletters.