In my twenties, I dated with unimaginable velocity. I flitted between Toronto and New York, often making plans from the airplane for later that evening. There was the high school math teacher who wanted to be a filmmaker, the philosophy professor (two, actually), and a random sampling of creative directors from major cities. In the warmer months, I always felt dangerous and attractive, never wanting to date someone for too long.
Having dates with different people each week became a part of my routine, and eventually bartenders began to recognize me. “Who’s this new sucker?” they’d coyly remark. Or they’d offer opinions on the men I would meet: “I didn’t like that guy, he didn’t dress up to meet you.”
Part of the appeal was witnessing my effect on someone. I was enthralled with the never-ending push and pull. There was also the glamour of the situations I put myself in that invigorated my sense of possibility. I was once flown to Cannes on a whim by a film executive, then days later, got a man I’d met in London to meet me in Paris. The dating dance became reflexive and anthropological. I collected observations, circumstances, and archetypes, which all made for good stories, but what exactly was I doing it for?
Dating at this pace required a specific kind of time, attention, and administration. If you faltered for a moment, the entire structure you built for yourself was prone to collapsing. Sometimes I confused which stories I had told to whom and basic biographical facts. Not to mention all the bad dates I would go on, and there were many. It was tough for me to end things after one drink. There was always another button to push and I was curious to get to the bottom of why the date was so bad. Some reasons were obvious: A man once called me a “stuck-up bitch” and another said he didn’t like me because I had no “self-doubt.” Frankly, I admire the moxie.
Sometimes I’d stay for another drink and on the way home, duck into a bar and meet someone new. It was like I was wringing each experience out to its very last drop. I wanted to know how much was in there, but I was too young to be discerning. It was a decade of being more curious about myself and my own power than being interested in connecting with other people. (Not to mention falling in love, though that did happen a few times, accidentally.)
Now, in my thirties, my love life has been much more temperate. Mostly because I’m no longer inexhaustible — but also, because I’m sensitive to the reasons behind my actions. If my twenties were the decade of saying, “You’re the problem,” my thirties are about interrogating myself and admitting that yes, at times, I’m the problem. (Most definitely.)
People often ask me what to do when they tire with dating’s never-ending dance. To which I say: Romance is not for optimizing. It is messy! Only go into it when you have the time and energy for the unexpected. When you feel fatigued, like anything else, take rest. This is also why I suggest never going to a dinner party in a bad mood — it really affects the atmosphere and that can trickle all the way out to the streets.
The more you whittle your ideal down to a strict list of qualifications — like the cottage industry of relationship advice instructs us to do with its list making, red flags, and icks — the more you suck all the spontaneity out of the only kind of adventure left in this modern life. Trying to avoid the electricity and pathos involved will lead to something worse than hurt — incredible boredom. As Anaïs Nin wrote in the preface to Delta of Venus, “You are shrinking your world of sensations. You are withering it, starving it, draining its blood.” Mitigate risk, not discomfort.
Which is why there are moments I dust off my old cap and act like a dangerous twenty-something again. Like a few years ago, when I was taken out for drinks, dinner, and dancing. Towards the end of the evening I leaned in for a kiss and the offending suitor said, “Actually, I’m kind of seeing someone I really like.”
Not one to take a loss, I went up to a man that had caught my eye earlier in the night, and in front of my suitor, told him that he was leaving with me. The next day, the offending suitor texted me, “I’ve never seen anything like that.” I tossed my head back, laughing, and feeling the rush of my youth. After all, it was always my own allure that I was most infatuated with.
I dated a lot in my 20s but with self loathing, not joy. You are so fun to read! More!
our crazy girl 🩷