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She could have been ... my girlfriend in Canada

But she didn’t want to meet in person

Love Letters

Love Letters

Q. I’m a man in my 20s and recently had a crush on a woman in her 20s. I met her online — she lives in Canada, about five hours away by car. We went on four virtual dates, with her asking me out on the second one. We had similar interests, political views, religious stances, and deep conversations over text. We had no problem roasting and joking with each other, whether it be over text or on a date. She even sent me a good morning text on the second day of talking.

On the third date, we both agreed that we were looking for something serious, not casual. That date lasted for over four hours! Additionally, she constantly talked about how toxic and immature her exes were, and while I’ve never been in a relationship, I opened up about some of my past dating experiences too. Toward the end of our fourth date, which was after three-plus weeks of chatting, I listened to the advice of my friends and asked her thoughts on meeting in person, which she said she would consider.

Some of those friends thought I could’ve asked her after the third date, but my gut told me that was too soon. Anyway, two days after date No. 4 she told me she’d rather continue being single, and made no mention of my idea to meet in person.


As a result, not only do I feel bummed, but I feel like the trust has been damaged. I’ve already made up my mind that I don’t want to continue talking to her for that reason. My question is: How do I trust women going forward? I’ve never been in a relationship before, and this is the second time in three months where a woman ended things with me without a clear reason. In both cases, it would have been long-distance, I asked them their thoughts on meeting in person, and things ended shortly after. I’ve tried dating short-distance and there are people I’ve met in person, but I’ve never gone on a second date in those cases.



A. “How do I trust women going forward?”

I want to start here because this isn’t about “women” or lies. Some people begin a courtship with good intentions, but change their minds about what they want after some time. That’s OK — and you might do it too, in a future relationship.

In this case, it’s very possible the distance became an issue when she thought about how the two of you would get together in person. In dating, sometimes ideas are nice, but when it comes to making it happen, the real hurdles look bigger.

This was a good lesson about your gut. After three dates — and many hours of bonding — you weren’t sure it was appropriate to ask to get together. Even though you clicked with her in important ways, you suspected she was not ready to make the next move.

You want to be with someone who will make it work in real life. You don’t want a girlfriend in Canada, and your gut told you this might not be a match.

Please go back to local dating. I know you haven’t made it to Date 2 at home, but you’re not alone there. People here will tell you they’ve been on a zillion first dates, and that in a dating-on-demand world, there’s a lot of quick talk, meeting up once, and moving on. It helps to treat first outings like a conversation at a party. Maybe something comes of it, maybe it’s practice for the next one.


One last thought: We’ve had a lot of letters from people who get invested in a new relationship, only to find out it’s not going to happen. I wish I could tell everyone when it’s worth getting excited about potential. Really, there’s no way to date without risking rejection and disappointment, but it does help to manage expectations until someone follows through on plans a few times. That’s a good place to start.



The problem with incessant messaging and texting and phone calling and Facetiming is: You build up expectations in your head, and eventually they come crashing down — as they did with this woman.


It’s silly to conclude that there are no good women close by. You need to get some perspective and keep trying with the most pleasant and positive manner you can muster.


Back in the day, when the only technology was telephone (without texting), it was harder because instead of this endless technological foreplay before meeting up, you actually had to pick up the phone, dial it, and ask your prospect out on a date. Like lunch, coffee, a drink, a movie. And be able to stand being rejected. Maybe, though, that was better. Then, you’d either get shut down or go on the date. Voila. Real time, real interaction where you can assess chemistry and proceed from there — or not. Try it, letter writer.



I once had an amazing, extremely long conversation with the nephew of my mother’s friend (blind date!). Met him in person. Absolutely no chemistry. Not interested at all. Gotta meet in person, letter writer!


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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