Dating in the Age of COVID

Chris on Monday. Travis on Tuesday. Collin on Wednesday. Chris No. 2 on Thursday. Daniel on Friday. Jacob on Saturday. And a double header with Matthew and Mark, fittingly, on the Lord’s day.

What might sound like a busy CEO’s appointment book—stacked meetings with high powered business leaders across the globe—is actually just a week’s cross-section of my post-quarantine dating agenda. For 120 days COVID ravaged New York City and my dating life, and in its wake left my highly curated, meticulously organized plan on how I was going to get back on my feet (and all fours) in the New York gay dating pool sprawled in a sexless heap. So what started as a fun way to release stress after being quarantined for four months quickly turned into consistently having to check my phone’s calendar to see the name of the man sitting across from me at dinner. Six to eight dates a week, hundreds of conversations, and countless backstories to keep straight—serial dating became an Olympic sport reserved for only the most mentally sound (or deranged) of individuals.

The art of dating takes on all new meaning in the midst of an international health crisis. One way I managed so many dates is that a lot of gay men think with their penises, not their brains. Out of the literal hundreds of men I chatted with online, not one of them batted an eye at the idea of meeting in person. I had dinner with dozens of men, all within six feet but all without guilt. Each date started with a maskless hug, and always ended with a hug and kiss on a street corner or an invitation back to my place for something more.

At the beginning, I was just excited to be eating outside at a restaurant again, much less with a cute guy. The idea of, once again, being able to be swept off my feet and into my bed was something I desperately missed and longed for. Was this to possibly fill a void in my own life? There was only one way to find out. I’ve always been outgoing, the kid who only got in trouble at school for talking too much, so meeting strangers nightly for conversation comes naturally to me. But what didn’t come as naturally was the emotional toll of a new man every night, the same mundane conversation as yesterday, and the realization after 60 seconds that I would never again see this person. Quantity far exceeded my desire for quality.

Where does your pursuit of happiness end and your ethical obligation to a complete stranger begin? As someone who has always struggled with crippling and chronic anxiety, who recently went through a brutal breakup and a called-off wedding, I often have the habit of putting too much pressure on relationships. The idea that if I don’t get an immediate response to my late-night text, if there’s an awkward break in conversation over dinner, or if he simply might not be interested, then my chances of finding a partner to share my life with instantly evaporates. However, the most freeing part of this summer sexcapade ironically wasn’t my physical relationships, the free drinks, or decent conversation. It was the concept that for once, I didn’t have all my eggs in the same basket. For the first time in my life, I dated with zero pressure, zero expectations and my dating life changed for the better because of it.

But the harsh reality of this experiment was the fact that other than outdoor dining and digital menus, I didn’t treat dating during a quarantine any differently than I would have a year ago. Maskless kissing didn’t really concern me, and clearly didn’t concern any of the men I was dating. I always was polite and discussed COVID protocol with my suitors prior to showing up, and the overall consensus was they felt no need to take extra precautions. Bringing men home was equally as normal, with the exception of a mandatory handwash, but the sex was even more routine. No masks, sometimes condoms, and throwing abandon to the wind. Because we were always two consenting adults, making our own decisions for our health, I’d like to think I wasn’t a villain in this story. I’ll allow you to make that decision from afar.

So I’d like to extend a special thanks to Chris, Travis, Collin, Chris No. 2, Daniel, Jacob, Matthew, Mark and the 26 other men (yes, I counted) who, over the last four months, unknowingly led me down the path I never knew I needed to travel. But above all else, I owe even more gratitude to the unsung heroes to this tale. My friends, who never judged me or made me feel guilty for working through my relationship issues over dinners, my colleagues for listening to my morning recaps, but, most importantly the waitress who saw me five times a week at my local bar and never blew my cover. Instead, she always threw me a free round to impress my date.