I Can’t Get This Dating Thing Right

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I turned 41 this year. I was married but got divorced after eight years, and we have children together. 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 this guy for four years.

During COVID, I started analyzing the relationship. I realized that I was in a relationship that didn’t seem to be growing. It felt like I was with a good friend instead of being with 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 didn’t date for a year. Then I tried online dating and went on two dates. 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. I would answer him but I noticed he never called. He reached out to me a couple of times to meet up. I attempted at first but then I assumed 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?

– Wrong


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

My only thought about that one 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 when to walk when 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.

– Meredith

Readers? The LW is feeling hopeless. Can you help?

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