The best of 50-plus dates - The Boston Globe (2025)

The past month I was seeing someone and it felt different. Granted, we only hung out a handful of times, but I felt a strong intellectual connection with her, we would talk for hours and hours, texted a ton, and had good sexual chemistry. I slept over her place a couple of times, which is rare for me, as I generally don’t like doing that so soon.

Then we went home for holidays and it was like a switch flipped, and texts from her became less frequent, etc. When we hung out for the first time after, she told me when I was leaving the following morning that she didn’t feel a romantic connection.

What happened? Did things move too quickly and she got cold feet and pulled back? I know she has a difficult family situation, so perhaps the holidays triggered something?

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Or am I simply not accepting that she might just not like me as much as I like her? Do I try again with her? Or just leave it alone?

PULLED BACK

A. Don’t contact her again. You’re better off letting go and moving on.

It’s is an absolute bummer that there was a big connection and then nothing. Maybe things moved too quickly, or there was an ex around during the holidays who told her he loved her. Perhaps her complicated family situation reminded her that she doesn’t want to be in a serious relationship right now.

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All we can do is guess.

It’s disappointing, but maybe this will give you more empathy for people on first dates who are very awkward … or tired … or need a bit more time before they can show you the best parts of themselves. Maybe you’ll learn that some of those people are tentative because they’ve been through similar experiences.

You can also ask dates about their pace — because it can be a revealing question. Maybe they’ve never considered what they’re like when they get to know someone. Or perhaps they’ll say, “Come to think of it, I get intense and burn out every time.”

A person once said to me, “I’m a slow burn,” and that told me a lot of nice things. One, they were self-aware. Two, I could take my time. Three, if all went well, there’d be heat.

MEREDITH

READERS RESPOND:

Maybe you have unfinished business from the breakup of your five-year relationship. If so, some people can go on for years having difficulty accepting the significant other is gone and unsure how to grieve the loss and move on. They compare everyone after to the ex, and those new people typically fall short (e.g., 50+ first dates and just one that seemed “worth investing in”). Such a person may fall very hard very fast for that “one.”

JIVEDIVA

Who knows what happened. People have their own internal things going on and many times don’t share them. The important thing is you were respectful and moved on. Overall you seem to have a great attitude about dating and are willing to put in the time and effort to keep meeting new women. Stay positive and friendly; don’t let this one blip break your stride. Good luck!

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LUPELOVE

She’s moved on, and you should too. Don’t waste your time and energy looking back. I’m guessing most people (myself included) have been on both sides of that situation.

EMPRESSETHEL

You’re rifling through a high volume of people, and you might be moving on too soon with a few or many of them. I think it’s really unfortunate that you’re making such rapid-fire decisions. What if even one person in those 50 people could have turned out to be a romantic fit for you if you’d given it just a bit more time? I suggest you take the time to self-reflect on why you feel your approach needs to be at warp speed. Rushing like that is a guarantee that you’re going to miss something. Figure out what’s behind your “trouble landing on someone that feels worth investing in.” Fear of commitment? Unrealistic standards/expecting perfection? Better to stop the revolving dating door and look within yourself.

EACB

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 wherever you listen to podcasts. Column and comments are edited and reprinted from boston.com/loveletters.

The best of 50-plus dates - The Boston Globe (2025)

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