Vanessa is a 26-year-old digital communications strategist who lives near Dundas and Ossington. She says, “Style is important to me. I prefer very structured, but feminine, pieces, and I worship Alexander McQueen, pre–Sarah Burton.” Vanessa says she has a “strong personality,” and that her friends would say she is “exceptionally caring. ‘Amazing’ and ‘awesome’ tend to be the most commonly used adjectives.” She met Niles online.
Right away, I liked Niles’s tenacity, the fact that we share a strong work ethic, and that we both thrive in high-pressure situations. Our first date, on the seventh of February last year, went so well that Niles asked me if I’d like to go out again the following week, “on the 14th.” He didn’t mention the fact that it was Valentine’s Day. I said yes.
He insisted on planning the whole evening. First, he asked me for a list of my favourite things, but wouldn’t tell me what the plan was, which made it difficult to choose an outfit. Every time I asked what to wear, Niles said, “You’d be perfect in anything.” The day before the date, he told me that I would be meeting him at the W Burger Bar on College Street, and that our evening would proceed from there. (I had mentioned that their boozy milkshake was one of my favourite drinks.)
I wore a cobalt cocktail dress and six-inch heels, and he was in an immaculate three-piece suit—we really didn’t fit in with the regulars. He offered me the cherry off the top of his shake, which was really sweet. It was only our second date, but his disarming personality made it very easy for me to act flirtatious about whipped cream and cherries. Once we finished with our shakes, he took my hand, and proposed we take a walk.
We strolled down Yonge Street, holding hands, talking about work, life, and other things. He was a perfect gentleman throughout: He held doors, helped me with my jacket, and even offered to carry my ridiculously large purse.
When we got to Richmond, he announced that he was going to take me to one of his favourite places. When we arrived at Cloud Gardens, which is truly breathtaking even in February, he told me to wander around. By the time I had returned, Niles had set up a little silver platter with all of my favourite dark chocolates. It was incredibly thoughtful, and I was feeling very spoiled.
After we’d sampled the chocolates, he asked me to dance, which I laughed at—there wasn’t any music. Then, he took his iPad out of his bag and queued up a custom playlist. We slow-danced for about half an hour, grinning at each other like idiots.
At the end of the date, he walked me to my door and kissed me goodnight. To this day, Niles maintains that he didn’t know he had asked me out for Valentine’s Day.
Vanessa rates her date (out of 10): 10
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