Rebecca is a 27-year-old administrator from the Beaches. Of her fashion sense, she says, “I’m pretty adept at mixing ‘tomboy’ with ‘girly-girl’ and ‘hipster,’” and prefers thrift stores and vintage to the mall. In her free time, she plays with her dog, hosts girls’ nights, and explores the city’s parks and gardens. After being “mostly single” for four years following an “over-the-top dramatic” long-term relationship, Rebecca met James online.
My friends say I am way too picky, and a few traumatic experiences have left me feeling very shy. I’m not really into messing around, but I signed up for OkCupid to see what was out there.
James messaged me right away, and I liked his profile. He seemed like a mix of musical, quirky, tough, nerdy, cute, and, well, more nerdy. He ran his own business, which impressed me. In the past, I’d supported exes through multiple job losses and was feeling anxious for some kind of stability. James seemed like someone who was both creative and had it together. I value those qualities myself, but a nod of approval from my parents is important to me as well. My father is pretty much a woodsman, and has ways of quietly intimidating my less-skilled boyfriends—especially ones who grew up in the city.
James’s message was the first one I actually responded to online. He had solved the riddle in my screen name to determine what part of Canada I come from, and it turned out we grew up maybe 100 kilometres from each other out east. I soon found out that we worked in related fields. He had chosen the same profession, in design and construction, as his dad. When he mentioned where his dad had worked before retiring, I realized that my dad had worked there, too, on and off since he was a teenager. I was so curious, I had to email my parents. My dad wrote back describing his total admiration for James’ father, their shared work projects, even hunting trips they took, dating back to the ’60s. I had to tell James who I was. Apparently, he grew up hearing stories about my father’s antics, and had always thought of him as a kind of superhero.
We spent about two weeks writing back and forth before investing in a real-life date. The entire day before we met up at Trinity Bellwoods Park, I had butterflies and couldn’t eat. We walked up Ossington and along Dundas and hung out at the Communist’s Daughter and The Red Light. Everything was perfect. We talked at length about our families and laughed about the amazing coincidence. After some drinks, we walked to the Lakeview to get something to eat. We held hands across the table like giddy teenagers sharing a milkshake.
I invited him back to my place. We totally got it on. Usually I wouldn’t do that on a first date, but it seemed like we had known each other for a really long time—practically our whole lives. I took down my online profile the next day.
Rebecca rates her date (out of 10): 10
Want to be a dating diarist? Email datingdiaries@thegridto.com.
