Liz is 28 years old, currently “funemployed” (but looking for a job in public relations), and living in the Annex. She says, “I’m shy, friendly, sweet, and sarcastic,” and describes her personal style as eclectic and very feminine. “I’ll admit that I’m a relationship person,” she says, “but with Toronto’s hook-up culture, it’s difficult finding someone who wants a commitment.”
About a year ago, I met Sam through the trivia league we are both in*. I saw him almost every weekend. We always shared some mild flirtation, but he wasn’t my type: Sam is a hippie, an intellectual, and a vegetarian. I am not. He wears thick, dark-rimmed glasses, and not the hipster kind—more like Leonard from The Big Bang Theory. He is also a short, nerdy guy and I am a 5’7” blonde fashion enthusiast. How could we possibly relate to one another?
Sam invited me to his birthday party, but I didn’t go. Instead, I messaged him a “Happy birthday!” on Twitter, after which he invited me to go to another friend’s party. I was uncomfortable not knowing anyone there; I ended up sitting in the washroom with a plate of food. The date was not going well. At the end of the night, we kissed, but it was awkward. I couldn’t look at him after it happened, even as Sam was getting off the subway to leave.
He ended up asking me out again and I felt like I should go. I arrived 20 minutes late without an excuse, but Sam was fine with it and accepted my hug and apology, no problem. We had drinks and dessert and the conversation was easy and flirtatious. We just talked about whatever, and there wasn’t the pressure that comes along with getting to know someone. After a few drinks, he started getting blinky. At first, I thought he was coming on to me—and almost winked back at him—but as the winking became more rapid, he explained that he gets blinky when drinking, which I found adorable.
Sam invited me back to his place afterwards. I was feeling good and boozy, so I went. On our walk, he suddenly kissed me hard and passionately. I didn’t expect it. At his apartment, things were obviously headed to sexy town and I was getting nervous. He offered me a drink, which I enthusiastically accepted. We started kissing on the couch. He’s a sweet kisser; he rarely uses his tongue, which I’m not used to, since most guys over-use it. Sam started feeling my body through my clothes and, soon after, my top and my bra came off. Upon seeing my breasts, he exclaimed, “These are lovely!” and I started laughing hysterically. I’d never heard my breasts described that way. It was really sweet.
We moved into the bedroom where things really heated up. The sex was great—thrilling, teasing, surprising, and satisfying. I think it’s true what they say: Less conventionally good-looking men are better in bed because they try harder. The hottest guy I ever slept with wouldn’t even go down on me. I loved that this mild-mannered nerd was so hot in bed. As it turns out, it didn’t matter that Sam wasn’t my type, physically or otherwise.
Liz rates her date (out of 10): 9
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UPDATE, SEPT. 4, 2013, 11:30 A.M.: Certain details from this article have been edited since its original publication.