I can’t get this dating thing right


After my separation, I decided I would do some introspection. I wanted to look at why my marriage didn’t work and what exactly I was looking for in a relationship — and I did just that. I stayed single for a few years. Then finally I decided I was ready. I dated another person for four years.

During COVID, I started analyzing the relationship. I realized that we didn’t seem to be growing. It felt like I was with a good friend instead of a lover. After thinking about it, I decided we should end things. He was bitter at first but then he came around and now we’re good friends.

After the breakup, I didn’t jump into another relationship. I stayed away from romance for a year — then I tried dating apps. I thought the first guy I met was the one. He knew exactly what to say. Before I knew it, I was on a flight to New York to be with him. Things turned sour fast. He wasn’t what he said he was. After a few months of going back and forth with the relationship, I realized it was all a sham. I ended things. I was so hurt and still am.

Right after that breakup, I went out with some friends and met another seemingly nice guy. However, things moved very quickly with this one. Literally right after our first date we were in bed. I felt guilty and wanted to treat him like a one-night stand. He messaged me from time to time, but he never called. He reached out to me a couple of times to meet up. I attempted at first, but then I began to assume he just wanted to meet up to have sex.

Over the weekend, he messaged me, saying we should meet up again. I said no and sent a smiley face. He went off, saying that speaking to me is a turnoff. I sent another smiley face and left it at that. We’ve not spoken since. I feel like I don’t know what I’m doing. I feel like something’s wrong with me. I feel like I’m not going to find a partner and I’ll just grow old by myself. What am I doing wrong? Is there something wrong with me?


A. I don’t know what was up with the last guy. The smiley face thing is confusing, and I’m not even sure you liked him.

My only thought about that specific experience is: Don’t play games. If you’re wondering if an evening was a one-night stand or the start of some good dates, just ask. No emojis to keep people guessing.

I know it seems like you’re lost in this process, but from the outside it doesn’t look that way. Since the divorce, you’ve had a bunch of experiences that taught you lessons. You’ve learned how to walk away, if something doesn’t feel like love. You also understand that big feelings — especially the kind that involve flights — can burn out quickly.

Hopefully, with this recent experience, you’ve learned to ask for clear communication.

This is a process, and it leads somewhere — hopefully to a place where you have more love for yourself, and maybe someone else. Take another break if you want to clear your head, but please know that looking for love can be strange. It’s not a linear path to one person who makes it all perfect.

Be patient. Enjoy your kids. Let life unfold.



That’s all time well spent. Just because it hasn’t led to another marriage doesn’t mean you’re failing.


One thing I notice from your letter is that you prefer to stick to the inconsequential details and skirt round anything messy or emotional, etc. Mistakes are part and parcel of the human condition. If you haven’t stopped to learn from those mistakes, then you are more than likely still making them.


This is called dating — you try people out and see who’s a good fit. Doesn’t mean anything is wrong with you. You are not going to be alone for the rest of your life — well, as long as you stop using the smiling face emoji to get your point across.


Send your own relationship and dating questions to [email protected] 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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