In a world where I can click my way to a MasterClass on topics as varied as how to think like an FBI profiler, how to make a concrete bench out of sand, and how to dribble like Steph Curry from Steph Curry, it’s outrageous that I can’t find a virtual primer on how to act on a date. I don’t even need someone renowned for her prowess like Elizabeth Taylor, married and divorced so many times she could have shared a thing or two about what to project during and expect from first, second, and third encounters. I’d just like two people with real adult dating experience to role-play some of the well-worn scenarios that a fortysomething who finds herself on the market again (after years away) might encounter.
I should note that I never dabbled much in courtship in the first place. I was and still am kind of alarmed at the idea of purposeful dating—meaning you and I go out together with the purpose of seeing if we like each other. Perhaps this is because as a young woman growing up in the Howard house, I felt as though my job entailed making sure everyone liked me. I was quiet when it was time to be seen and not heard, funny when the silence needed to be broken, and provided an open ear when someone needed to vent. On dates, I excelled at my childhood job in what must have looked like an impersonation of one of those birds in the rain forest that fan out different feathers to try to capture a love interest’s fancy. The performance prevented me from considering for even a second whether or not I actually liked my dates.
By my mid-twenties, I had therefore all but given up on the enterprise, and the only date I went on during the first two years I lived in New York was with a balding, heavyset man I encountered on the very first dating site, Match.com. At the time (and maybe still), I thought meeting someone on the internet was the silliest thing imaginable. Plus, I never ever would have seriously deemed this man, who was more than a decade my senior, a potential boyfriend, so the venture seemed safe from a rejection standpoint. It was okay if he didn’t like me.
He and I met at the wine bar below my apartment. We chatted over a glass. Then he asked if the date was a prank. I legitimately didn’t think so, though in retrospect it was most certainly a joke—but pointed where? I don’t know. A few months later, I took a more comfortable path to romance and got involved with a coworker friend. My days of dating were officially over (or so I thought), and aging men on Match could scroll with confidence, knowing they would not be trolled by a twentysomething with a strange sense of humor.
That is, until I joined the beleaguered ranks of all the other people who filed for divorce in the wake of the pandemic. Turns out it’s time to date again, and it’s quickly become clear I have not been training for it.
My first date right out of the gate was an absolutely shocking experience I’m sure neither party will ever forget. (In my defense, my only insight into the sport over the last two decades has come from rom-coms, and we all know Carrie Bradshaw and Emily in Paris never go on a date in which no drama happens.) For starters, I picked a man who was also getting divorced, also worried about what that meant for his kids, also vulnerable and lonely, but decidedly not interested in living out the cliché where all humans at the end of their marriage soothe their pain or celebrate their freedom in the arms of someone new. He did not want to do that, even after I assured him multiple times that he’d regret the decision. Frankly, I’m not certain I wanted to do it either, but TV had me convinced that attempting some version of this scenario was the thing to do.
That incident changed the way I refer to first dates. Now I go on “possible friend meetings.” Renaming the endeavor puts me in a more casual mindset that’s less focused on results. What I’ve found, though, in my limited collection of these friendship meetings is that my counterparts don’t know what to do either.
In this overdue age of gender equality–ishness, men appear to be floundering through a new list of rules they only half understand. And women (at least this one) want to be treated as the equals we are but also want to just be old-school-style treated. On a recent friendship meeting for coffee, I was shaken from my frame when the barista swiveled the sleek swipe machine to face us and my “friend” matter-of-factly clasped his hands behind his back and looked to me to fetch payment. I tapped my card.
We drank our coffee, and at the last drop, the fact that I had paid and he hadn’t bothered me less than I had anticipated. After all, I had invited him to join me for the caffeinated beverage. What if he only drank water and never spent money on water derivatives? Why should he have to pay for the expedition I had planned?
On our walk out of the hipster corral I had selected for friendship making, my new buddy asked if I’d like to go out again. Imbued with the power of paying, I said sure, but only if he planned what we would do from top to bottom and, as a result, bore the expense of it all. And, I told him, I didn’t want to go to dinner, because that was too obvious. My demands may sound impolite and extra hefty for an oat latte, but I intended to do us both a favor. I may be new to dating, but I am not new. I am forty-five years old. I know what rubs me the wrong way and what trips my trigger, and I also know I’ll breach menopause before I find a “new friend” if I don’t push past the co-planned, politically correct, split-bill experiences and see what kind of feather suitors throw up without my help.