As You Get Older, Should You Date Women Who Want to Reconnect?

It’s been years… and now she wants to reconnect. Should you meet her? And beyond that, should you date her?

I received an email recently from a girl I hadn’t heard from in six or seven years.

I’d known her from social circle (back when I still maintained a social circle). She was skinny, fun, and cute, with an endearing California Valley girl accent (and all the expressiveness that entails). She also had that somewhat uptight air about her that can be a little off-putting but is really fun when you break through it and reach the real her.

Anyway, this was not a girl I’d hooked up with. Didn’t really have a good opportunity, and in any event I slept with other girls from that circle who were younger and didn’t have the same walls up she did. I met up with her various times in our shared social circle. Toward the end of my time in that circle, I scheduled a one-on-one meet with her but had to flake on it... and when she wanted to meet again I wasn’t able to make myself available for it. And after that we were in different cities and she fell off my radar. She was 29 years old back then.

So I got an email from her after more than half a decade, just saying she saw an event and wondered if I intended to go to it and asking if I was in town.

And the only thing I could think was, “Wow, 36 years old and still single, huh?”