History repeats itself

I’ve been on a couple of dates with a new guy. Connected on Tinder last week, met for a beer on Saturday, went out again last night. After two dates, I really like him. We have a lot in common and laugh and have an all-around good time.


However, there are some red, or maybe pink flags, I think. The concerns, briefly:

  • He’s divorced – within the last year or two. I’ve been down this road before – with E. In fact it was right around this time last year. Current guy, B, was married for 11 years and it sounds like the marriage was over about a year and a half ago. Am I up for this? I have been the rebound, re-learn how to date girl before. Which seems great until you get dumped by someone who isn’t ready for anything serious. After E, I decided I wasn’t interested in playing that role anymore. But I don’t know enough about B yet to know what his intentions are and what he’s thinking. He also has partial custody of his two kids. It seems like he has a pretty good relationship with the ex. I am totally open to being with someone with kids. But is B ready to date?
  • He hasn’t paid for a date yet. This is another thing I said I wouldn’t do again after J this fall. So far, though, we’ve had a pretty even split – I’ll get this, you get that kind of thing. Still, even if you’re not going to spring for date one, by date two aren’t you going to buy me a beer?
  • He seems a bit flaky. We had tentative plans for last night. I finally had to text him yesterday morning to find out if we were on. He said he had figured out the childcare situation, so yes! And suggested we connect in the afternoon regarding concrete plans. I finally texted him at 6:45 to see what he was thinking. Annoying. 

Here’s the thing, though. He makes me laugh. I make him laugh. He loves sports and is smart (this combo is way harder to find than you might think). He even likes theater and live music. And after the first date he was pretty clearly into me. So we made another date.

Which takes us to last night. After the annoying communication hiccup, he came to pick me up (at my request) and we shot downtown. Had a drink, laughed, bought Wolves tickets on the street, went to the game and laughed some more. But we never quite hit a second date stride. I kept waiting for a touch or a comment or something to make me believe that he was interested in me in a way that was more than just sports buddy. It never really happened. He drove me home (we walked to the car without so much as a hand hold or a arm link), he dropped me off. There was a short-ish kiss. He made a vague mention of talking soon. Seems like the ol’ brush off.

Throwing caution to the wind, I texted him a quick thanks and good night, he responded in kind. I sort of think that was perhaps the beginning and the end of B. I also think that maybe 2015 is a year that I’m going to take some more risks. I saw somewhere that I should just assume he likes me until he lets me know otherwise. I don’t really know what he’s thinking. So I’m going to do the opposite of my instincts and assume that he likes me for now. I will contact him again and see what happens. Maybe we’ll go out again, maybe not.

I’ve got that match.com membership waiting for me to pull the trigger, just in case.