First Date with The Flippy Top

I’m in a weird mood. Literally the day after Jessie sent me that long email, I had a date with this new woman I had been emailing for a while. She found my ad in this classifieds handout that is going around Toronto. I dunno, we were having a nice email exchange. I wasn’t sure how I felt about her, because it’s hard to know someone without meeting yet. And we were supposed to have a date the other week, but I got sick so it got moved. Anyway, we finally got together for coffee for a couple of hours and talked and it felt really like, natural, and I think intellectually we really clicked. We talked about art and film and tv and I found out she is a writer and does reviews for a local newspaper. She’s smart and cute and sometimes she would give me this sly sexy smile that sort of seemed sweet. I found it really promising, and I hadn’t had high hopes for it. She knows submissives don’t just lay there so that is definitely a point in her favour ha ha ha.

At the same time part of me is like. Am I ready for this when I just finished having such an awful experience with Jessie? Like Jessie was never a girlfriend or a date, but there was some intense stuff there that for sure all went sideways and it’s over now but also like oh man, I just worry so much about leaping into something new without a bit of a buffer between that experience and this one.

And I guess part of me feels like the last ten years were so awful, romantically speaking. People really didn’t regard my feelings very highly. I got used for sex a couple times, and discarded almost as fast. Women sort of wanted emotional relationships without being honest about being into me. I had like a couple girlfriends who weren’t girlfriends and yet were. Ugh I mean I guess I’m just wary of that pattern repeating. I know this new woman wants something possibly, and it’s going to go slow if it does happen, but part of me is still reluctant to get pulled into something that isn’t real, or doesn’t treat me well.

At the same time I know I have to take an emotional risk again. Like I can be smart about it and go slow and see what happens, but ultimately I have to be willing to be hurt again if I want to have a loving relationship with someone someday. It’s hard. This time it’s a bit easier because she isn’t part of any orgs I work with, she isn’t really in my friendship circle, if it doesn’t work out it will be okay and we can drift apart. She lives on the other side of the city. My friend M calls her “the Flippy Top” so I guess I’ll use that diary name for now ha ha.

We are gonna have another date, and told each other in emails after that we think the other is “super cute.” So there definitely seems to be a spark here. I dunno! We won’t see each other for a couple weeks though, my Mom comes next week, then she goes to Nashville, then her Mom comes here. So we’ll be busy. But that’s a good thing. We both have busy lives, which is a bonus. And she’s seen my OKC and knows a lot about me based on that and what I am looking for. I haven’t sussed out if she has any interest in children though, which is kind of a big deal right now.