Sometimes, spontaneity lights the spark: Dating Diaries

A problem that comes up a lot in the Dating Diaries, the Toronto Star’s popular relationships column, is the predictability of dates, especially first dates between people who met online. As dating has become less about magic and spark, and more about the law of large numbers, daters often rely on a tried-and-true pattern, like chatting online for a few days or weeks, maybe talking on the phone, and then meeting for an afternoon coffee or after-work drink. (Do you have stories to tell? We want to hear them — details on how you, too, can become a dating diarist at the bottom of the piece.)

These dates tend to be cheaper than something like dinner and a movie: they’re less of a time commitment — some power-daters even line up a few dates in a row, which also means only getting done up and dressed up once — less of an emotional investment, and might also be physically safer.

But, that sameness can be wearing, especially for someone who dates a lot. (The cold calculus of it all is not particularly romantic, either.) It can be hard enough to get to know a new person in an hour or two, and when you’re in the same kind of location, doing the same kind of thing, it’s easy for those dates to blend. A potential solution? Some of the most successful dates in the Dating Diaries, whether or not the daters went on to develop a relationship, are all about spontaneity.

“Lesley” spent a few days chatting with “Sunil,” and “after volleying a few suggestions back and forth, we settled on a date that was 10 days away.” However, “one night soon after we set the date, Sunil mentioned over text that he’d finished work — it was just after midnight — and I said something like ‘You know, the bars are still open.’” Lesley wrote that she wondered “what kind of message I was sending,” while Sunil “didn’t want me to feel pressured.” They agreed that neither of them was going to get anything else done that night, “so what harm would a beer do?”

The date went well, and they “ended up closing down the bar,” and going back to Lesley’s place. She wrote “We stayed up until just after sunrise talking,” a spontaneous way to end a spontaneous date.

Dater “Sasha” met her date “Jonathan” — who was “very manly and handsome and looked like Thor” — at a conference, and wrote that he “seemed to be focused on me, and not distracted, like I had his full attention always.” That’s just the kind of person to have a spontaneous date with, which is what they did when Jonathan was in town for work, and asked Sasha to spend the day with him. “He didn’t tell me what the events were, but he did let me know to wear walking shoes — no heels!” They got coffee, walked around, talked, kissed, drank and ate. Nothing unusual, but Sasha loved how “in the moment” Jonathan was, and wrote that while he guided them around, he “gave me the freedom to express myself and my desires.”

Even before her date with “Owen,” our dater “Regina” was in “‘yes mode,’ saying yes to whatever came my way.” Owen “seemed like silly and random fun, and was definitely cute” so she agreed to go out with him, and asked to “meet at a public place and go from there.”

Regina didn’t feel a connection, and was slightly embarrassed when Owen wore a fedora and feather boa around Kensington, but she was game anyway. She wrote “It seemed like we were almost in hyper-mode. We went from shop to shop, and stopped in at more than a few bars and restaurants for drinks.” The date, however, might have been too spontaneous: Owen “seemed like he couldn’t sit still. At no point did we get into a deep conversation; it was all action and surface.”

Spontaneity led to more depth on “Christina’s” date with “Serge.” Leaving a bar with colleagues, Christina encountered Serge, who was also “mostly there to look out for the people we were with.” He was “very handsome” and gave Christina butterflies. In under an hour, they “connected in such a way that it felt like we’d known each other our whole lives.”

Christina wrote that after their friends were “safely tucked into separate cabs, Serge and I continued to hang out. We didn’t discuss it, it was just natural.” They went to a diner, and got “even deeper” into their conversation. Christina wrote “I was able to open up to him about my life and my past relationships, all while we were both sober and hadn’t slept for almost 24 hours. It was like our souls had connected.” The date ended after they drove to the lake to watch the sun rise. Christina wrote “the date felt life-changing for me.”

How often will a cup of coffee feel like that?