Sadie is 38, lives in Parkdale, and works in entertainment. She is “bright, interesting, a good time and a committed, loyal, caring friend.” Sadie enjoys trying new cocktails, fashion, long weekends away with girlfriends, and reading fiction. She says that she is interested in guys who are “honest about who they are, and what they want” and that her dating life is “always something new.”
Will and I work in the same industry but we had never really crossed paths. I always thought he was good-looking and cool. It turned out Will felt the same way about me. When we finally crossed paths, he asked for my number right away and made it clear he had been keeping an eye on me and my career. I gave him my work number for some reason.
He left me a voicemail that I listened to over and over. I would have made my girlfriend listen to it if I could have figured out how to send it to her. I was already imagining being in a relationship with Will. I actually got it in my head that maybe he was too cool to date, that he’d be one of those guys who you can never pin down and never relax with. I was stewing about it even before I called him back.
We made plans to see a movie. He didn’t mention having dinner or getting drinks, he just asked if I wanted to see this one specific movie with him, at a specific time and location. I liked that he had an actual plan. I read a bunch of reviews of the film. Will had seemed really excited about this movie and the director. I always think that one of the best parts of dating someone is being exposed to the stuff they love and are passionate about. It’s like getting a contact high.
I spent a lot of time getting ready. Will is around a lot of attractive women at work, and that really threw me for a loop. I felt like I had to create a new, sexier identity or something. My excitement about Will was transforming into a blow to my confidence. I never act like this when a guy seems like he will be underwhelming. Maybe that’s why I date so many underwhelming guys.
When we met up, Will was so laid back that it seemed more like he was randomly running into me than taking me out. I tried to remember how he had been when we first met, which was at a work event. I assumed he was either nervous and covering for it, or just that cool. He had already bought the tickets but when I offered to get us some snacks, he said he was fine.
I tried to talk to him about how he had called me and made the first move after we met, almost in a teasing way, but he didn’t really respond to that or pick up on the flirtation. He wasn’t closed off or ignoring me, but he was clearly not acting like he was on a date with someone he liked and wanted to impress. I noticed he was wearing sweats, and decided he wasn’t nervous at all, which somehow made me even more nervous!?
I talked his ear off as we were sitting there before the show. I could not shift into a less anxious state. I was in “fawn” mode. His coolness was making me absolutely crazy. I realized I am so used to being the more detached, “impress me” person on a first date and feeling like I had given up that power left me not knowing what to do.
I went to the bathroom to give myself a little break and felt a bit more composed, But getting back to my seat was a bit of an ordeal, as it always is, and I felt sweaty and graceless. I accepted defeat at that point.
We both liked the movie, and I was hoping that since Will had been so into it he would want to go somewhere for a drink or some food to talk more about it with me. I wanted another shot to be normal on this date. Instead, he hugged me goodbye. We didn’t go out again.
Sadie rates her date (out of 10): 5
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