Travis is a 35-year-old investment banker who lives in the Entertainment District. He says he is “the most charming, narcissistic sociopath you’ll ever meet, but also a down-to-earth guy,” and describes his dating life as “active, but not out of control.” He says, “I’ve been looking for my soulmate, but I admit I might have been looking in the wrong places.”
Stephanie was a bottle-service waitress at a King West nightclub, and I met her when she was serving me and some friends. I asked her out, and the next week we went to Sassafraz in Yorkville. When I arrived, the crowd appeared unusually stuffy and I was worried that Stephanie would be intimidated. When she arrived, however, she looked magical, as if she had just walked out of a photo shoot. I was the one who was intimidated.
When she sat down, I suggested we split a bottle of wine. I also went ahead and ordered a double vodka on the rocks to help calm my nerves. Stephanie liked my style and ordered a vodka and water for herself. I felt an immediate connection, but then again, the majority of the girls I take out drink quite a bit—likely a direct correlation to the fact that 98 per cent of them work in a bar or club—so I decided to keep my expectations to a bare minimum.
The date actually went very well. There was a lot more about Stephanie to be attracted to than her looks. We ended up ordering tons of drinks, and eventually she opened up and told me about how she never goes on dates, but knew there was something special about me. As the drinks kept coming, we got pretty loud, and the waiter subtly brought the bill while we were still drinking and finishing dessert.
After that, we went to a King West bar where it was “industry night.” Stephanie had gotten the attention of a few promoter-type guys and was being hit on pretty hard. I wasn’t overly bothered by it initially, because it wasn’t my first time dating a girl like Stephanie, so I knew what to expect. However, I decided that I needed to shift the competition back in my favour.
I walked around to see if I knew anyone else there. I saw Kelly, whom I had met at the same bar a few months before, but never really talked to. She looked hot; I was excited to see her. She was also pretty drunk, so we hit it off immediately. I kind of forgot about Stephanie and just got caught up in the moment.
Kelly insisted on ordering numerous rounds of shots. We’d been hanging out and flirting for a while, but when I told her I needed to go find a friend, Kelly pulled me towards her and suggested that we go back to my place. After giving it some thought—five seconds, maximum—I agreed and we took off, leaving both of our jackets at coatcheck in the process.
The next day, I woke up to a few angry text messages from Stephanie, but the bar had been crowded enough that I was able to create a good excuse for leaving early. All in all, a good night.
Travis rates his date (out of 10): 7
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