The best of 50-plus dates

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Q.

I’ve been single and dating for about two years now, after a five-year relationship throughout the middle of my 20s. I’ve been on what feels like 50-plus dates in the past couple of years, a vast majority of those being first dates. I really have trouble landing on someone that feels worth investing in. 

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? 

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

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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.

All I can do is guess.

It’s disappointing, but maybe this will give you more empathy for the 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 had an experience similar to the one you just had.

You can also ask dates about their pace – because it can be a pretty 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? Reach out again? Why did this feel so important after a handful of dates? Was speed part of the problem? Have you had experiences like this?

What’s on your mind about dealing with exes, dating, love, loss, complicated friendships, work crushes, etc.? Submit your letter by using the anonymous form, or email [email protected].

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