Bethany is a 36-year-old publicist who lives in Yorkville. She says, “My style is a combination of ‘rocker chic’ and ‘bohemian.’ ” Bethany says that she “tiptoes the fine line between confident and cocky,” is an “adrenalin junkie” and that she “isn’t afraid to take charge and stand up for what I believe in.” She says, “I love track driving, movie marathons, bourbon, going to hockey games and jogging on the beach in the summer.” Bethany is divorced and has been single for six years and describes her dating life as “a Taylor Swift song.”

Before I decided to test the waters on Tinder, I was on a more conservative dating site, which is where I met Darryl. He sent a great first message about how he was the spontaneous type, always living in the moment, trying new things, living on the edge. I was entering serious cougar territory for the first time with Darryl, who had just graduated university. I think that the year he was entering high school, I had finished university and was married.

He was a tall, thin, apparently sexy skateboarder, and other than his height and good looks, he was far from my usual “type.” But, I was looking for something different, more meaningful. Maybe this was it, or maybe I just wanted to recapture my youthful, vibrant self. Plus, his age meant that he was less likely to want to give up his freedom and I was in that same place.

We messaged back and forth for a couple of days before organizing a time to meet, and when we did it was at a little tea shop. He was on time, but just like his profile had promised, seemed like a free spirit. After our warm drinks, we left to explore the neighbourhood. He told me right away that he hadn’t had a serious relationship since high school, because for him there was too much compromise and sacrifice.

We ended up at Hart House. After spending four years at the University of Toronto, I had seen my share of the palatial building, but I let him have his moment. He had an interest in architecture, he said, and I had a desire to be spontaneous. He took me on a tour. He had a flirtatious smile, but I mostly I felt like a tourist and like he was my guide. I did think that this could make for a fun role-play game, however.

We entered a room and went up a spiral staircase that led to a glass door. There, Darryl took my hands in his and leaned in for a kiss. I lost myself in the pure pleasure of it, even though everyone’s hands were well above the belt. That kiss changed the tone of the “tour” and led to some serious grabbing in front of some stained-glass windows. Darryl asked to come back to my place, but I said no.

We texted back and forth, but my life was so busy I couldn’t commit to dates. I went off the dating site, but returned a while later. Darryl had forgotten about me, and sent me the exact same first message as before. I curiously responded as if it was our first time corresponding. We organized a time to meet, and when I arrived, he didn’t recognize me. On our second “first date,” I realized that everything on our first-first date was planned, including the “spontaneity.” I found myself on the same tour, with the same first kiss and the same subsequent make-out session. The entire time, he never clued into the fact that we had done the same things before.

Bethany rates her date (out of 10): 5

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