Jeremy is 28 years old, works in marketing and publishing, and lives in Parkdale. “I guess my style is informed by Woody Allen, and maybe some Wes Anderson films,” he says, which means a lot of collared shirts, slacks, and suits from Sydney’s and Nomad. His friends would call him “cynical,” but he says, “I’d still like to think that most people think I’m nice.” Jeremy was single for four months before meeting Kendra.
I go on a lot of first dates, but very few second dates, for whatever reason. It might be because I’m bad at making plans. I’m looking for someone who doesn’t party too much, has a decent job, and some idea of what she’d like to do with her life. Also, having a dog would help.
I met Kendra through a mutual friend one night at a party. I liked her because she was cute, so I friended her on Facebook and asked her out on Facebook chat. We talked about how funny it is to take our small-town parents to restaurants like Mr. Greenjeans and Milestones and The Keg, because those restaurants are kind of expensive and try to be fancy but are mostly just mediocre. I jokingly asked if she wanted to get dinner at the Milestones at Yonge-Dundas Square. We made plans for that Friday; I was excited because I really like eating out.
At the time, I was unemployed and had some time to kill, so I met up with a friend of mine to drink some beers in the park. Two beers inevitably turned into four, which turned into six. I thought it would be a great idea to text this other girl, Jessica, since she lived around Trinity Bellwoods and also liked beer. I had met her at a party just like Kendra. Jessica was cool and seemed interested in art and other things that I like. Once she met up with us, my friend left. Jessica and I were hungry, so we decided to grab an early dinner at Pizzeria Libretto. I figured I would sober up and have no problem making it to Milestones in time for my date with Kendra.
Our early dinner ran a bit late. Jessica and I were having a lively conversation, and we seemed to have a lot in common. Then, Kendra started texting me that she was en route from Rosedale to Yonge and Dundas. I was enjoying myself, so we kept ordering drinks. A bit later, I got a text from Kendra saying that she was at Milestones, and was waiting for me at a table. I was pretty drunk at this point, so I thought I’d just hang around at Libretto. Kendra texted me a few more times and then stopped. Interestingly, I never received an “I’m going home, fuck you” text, which actually made me feel worse. Jessica and I left Libretto to drink more at her place, and I ended up leaving pretty late. I would have stayed over, but I really enjoy waking up and eating breakfast at my own house.
Jeremy rates his date (out of 10): 7
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