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Love Letters

I just flew to another city to have dinner with my work crush

I told her I had to be in her city for a convention, but really I just went to see her. Do I say something?

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Q. I’m a fan of the Love Letters podcast. Here’s my problem: I met this woman last year at work. We were at a convention and one night hung out with mutual friends. We started talking and it was great.

Fast forward, and everyone at the company went to Disney World. We met up there and hung out for most of the four days of the trip. We went to an arcade the last night, just us two. Nothing happened, no kiss, nothing. I think I had some chances but I never took them.


Then, six months later, I told her I had to go to her city for a convention, when in reality it was to see her. I flew in and we had dinner, great conversation, and a great time together. My friends had told me to make a grand gesture and I wanted to, but I decided not to in the moment. I thought that even if I tell her how I feel, nothing can happen because I’m in my city and she’s in hers (halfway across the country). We text once a month and it’s not dry at all.

Did I waste an opportunity? I still care about her, and if we lived a lot closer I would’ve already made a move, but the distance and the reality that neither of us really wants to leave our cities keeps me from letting my feelings out.

— Thinking About Her

A. I don’t think you missed an opportunity. Also, I’m not big on grand gestures, at least not at the start of a relationship. You followed your instincts and enjoyed her company. There’s nothing wrong with that.


Also, you learned that spending more time with her only made you want to see her again. That reminds me of the people in Season 2 of the podcast who had a revelatory moment about a maybe-significant other when they realized they missed them. It was a recurring narrative, that a person had a few great dates with someone, went on vacation, and then realized, “Oh, all I want to do is return to them.”

In your case, you might be realizing you’re more open to long-distance than you were six months ago. I mean, you flew across the country to see this woman. And if your instinct is to think about her all the time, analyzing texts and wondering what happens next, you might as well spend that energy making something happen, if she’s interested.

If you know that distance/moving is off the table forever, try to focus on others. But if the trip to her city felt necessary, you should think about what that means.

— Meredith


You answered your own question. Date local women! There are plenty of them available! REDSOXPATRIOTSFANNY

Just tell her. If she doesn’t feel the same way, you can move on and stop obsessing. WIZEN

Is this woman single? Do you know that for sure? I’d find out if she’s dating anyone before spending any more time analyzing this. DORA79

“Then, six months later, I told her I had to go to her city for a convention, when in reality it was to see her.”  Does anyone else think this is really weird? SOB77


Get Season 2 of Meredith Goldstein’s Love Letters podcast now at loveletters.show and Apple Podcasts, or wherever you listen. Column and comments are edited and reprinted from boston.com/loveletters. Send letters to meredith.goldstein@globe.com.