Tim is a 27-year-old supply-chain manager who lives at Yonge and Eglinton. He describes himself as pretty outgoing, helpful, and thoughtful. “A friend once said, behind my back, that I have a big heart, but he will only call me a ‘gross dick’ to my face,” he says. After ending a six-year relationship, Tim calls his dating life really weird. “I don’t know how to do it after having had a girlfriend for so long.” He met Lynn on OkCupid.
Lynn messaged me about a TV show we both liked. She seemed funny and looked cute in her profile picture. I asked her out by our third or fourth message. I was heading out of town, and asked if she wanted to meet me for a quick beer before my flight. We went to a bar in Bloor West Village. She was cool, but a bit too sarcastic. I was distracted thinking about getting to my flight and wasn’t on my A-game, so when I left, I said I’d like to see her again for a do-over.
She suggested a double date because her sister was single and bored. I brought my friend along, and we met at a patio on Markham Street in the Annex. My friend was late, so I did my best to entertain them on my own, which started with some buckets of PBR. Lynn started telling me a story about how she was a really committed runner, and her sister, who was sitting beside her, called her out for lying. Lynn was pretty drunk at that point. She also told me that she was getting off of OkCupid because she had met enough guys and was having trouble juggling them—or “us,” I suppose.
She texted with another guy from OkCupid through the majority of our conversation, as she ordered drink after drink. Lynn’s sister was clearly much nicer, funnier, and better in general to talk to. She was the one saving the date.
My buddy finally showed up and we all went down to a bar on Queen Street, and then to another place on King. By then, I knew that I was never going to see Lynn again, so after ordering some food for the table, I just kind of ignored her request for me to buy her deep-fried pickles, and kept talking to my buddy and her sister. Lynn hadn’t offered to pay for anything, which was a turn-off. I think she used dating as a way to get free drinks.
Near the end of the night, she mentioned that she had just booked a “job,” which meant that while we’d been out drinking she’d been answering a Craigslist ad to bartend a bachelor-party poker game in lingerie. Oddly enough, I think she told me that so that I’d be more interested in her. We had a weird, sloppy makeout when we left the bar and then parted ways. I ended up partying at a famous athlete’s place later that night when my buddy and I ran into a friend, so the evening actually turned out okay.
Tim rates his date (out of 10): 5
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