Demi is a 34-year-old financial analyst who lives in Roncesvalles. She refers to her style as “classy hipster, not the poor kind,” and her friends would describe her as “adventurous, always flying by the seat of my pants, and genuine.” Her ideal partner is “someone I can trust, who has something to teach me and who can pay for their rent and my dinner.” She met Mason on OkCupid.
I had just broken up with my boyfriend, who was still living with me, when Mason messaged me. I was bored at work, staring at spreadsheets, so I answered him and we chatted a bit. He was attractive, funny, and seemed humble, which is unusual for guys who message me online. We set up a date for the next week, but a few hours later, Mason asked if I wanted to meet up after work. I didn’t have plans until later on, so I agreed.
Mason looked even better in real life than in his pictures, and he hugged me like we were old friends. He was tall and a typical hottie, but also exactly my type—the kind of person who I have always imagined myself being with. We sat down and started talking and drinking beer, and we moved on to tequila shots pretty quickly. He asked questions and didn’t always talk about himself, which was a nice change.
I told Mason about my relationship ending, but I didn’t mention that my ex still lived with me. He told me about some douchebag stuff he’d done in the past; he was kind of a player. We actually had similar relationship histories and we’re both “suits,” so we were able to talk about work. An hour in, he and I both blew off the plans we had made for later that night. We got more and more drunk and ended up making out like high-school kids at the table.
As a general rule, I don’t go to someone’s place right after meeting them, but it felt natural. We left hand-in-hand, and when we got to his amazing penthouse apartment, he led me through his room and onto the balcony. The view spans all of the GTA, which was super-hot and magical. Things got more intense, and my clothes started coming off, so I was mostly naked in the open air. Suddenly, the door to Mason’s bedroom opened, and his sister—who was visiting—walked in. Her first impression was of me straddling her brother. She was coming out to smoke and didn’t know we were there. She seemed stunned. I rushed to put my clothes back on, and then immediately said to her, “Hey, remember that time you walked in on me naked?” which made it less awkward and more funny.
After that, I went home. Mason FaceTimed me at 7 a.m., which was amazing. I was giddy for a week after—actually, two months later, I am still giddy. We have since found many weird and wonderful connections between us that make everything that much more special and interesting in our relationship. I think he’s a keeper.
Demi rates her date (out of 10): 10
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