Is this out of line to ask someone?

I’ve noticed a self-sabotaging pattern where every few years, a particular type of woman goes out of her way to signal interest in me and it takes me so completely by surprise that it either goes over my head or I think I’m seeing things and I react in a way that must give the impression I’m not interested.

They seem like really good people I’d be happy to have even as friends, even more so as partners. There seems to be something they notice about me that others don’t because they go out of their way even if they seem like introverted, even shy, women who are picky. I’d like to not make that mistake in the future.

The only one I’m still in contact with is a woman I went to bar school with. When we were alone on the bus, she said: “There are a lot of good restaurants in town.” which lead to a deer-in-the-headlights moment for me and then I didn’t know how to handle it. It’s too late for that now as it was years ago. But it seems that my type has me as a type and I’m curious to know what those types are. We’re friends on Facebook. Is it out of line to ask her about it?

Yes, that’s kind of creepy, especially because you don’t seem like close friends if your main connection is by Facebook.

Two things:

  1. Have you been in relationships?
  2. You might be the sort of person who could benefit by spending some time just saying yes. Someone asks you to go to a restaurant with them? Just say yes. Someone asks you to eat food you normally hate? Say yes. Etc. Takes a lot of thinking out of the equation, because for a few weeks/months/whatever, just say yes.

That is, until your friend Skullcrusher gets out of Folsom and looks to spice up his newfound freedom with you. You can say no to that.

You’re right.

1: Yes, although I suspect they’re past relationships because we weren’t a good match. The women of this type seem much more forward to an extent that took me aback e.g.: a 15-year-old getting tickets to ask me out which I don’t think was common in the late 90s or even among adult women today.

2: Probably, yes. In some cases, though, there was a strange mix of forwardness and indirectness that made me unsure of what they meant.