I Went on a Covidate: Here’s How it Went

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And The book title is “Love in the Time of Cholera,” but it’s hard to not reimagine it for the 21st century.  Love in the Time of COVID, am I right? It was hard enough to find a special spark when we weren’t afraid to be around each other with our faces exposed.

I personally do miss kissing boys in cocktail bars while drinking old fashions, accompanied only by the flickering light of a nearby candle.

Those days are long gone and the only old fashions I’m drinking are solo and in bed with a battery-operated candle. Safety first.

I waitress at a restaurant in downtown Manhattan where every so often a man at my table will ask me for my number. Sometimes I’m flattered, sometimes appalled; it all usually depends on how they go about it, as well as their etiquette during dinner. I’ve dated a few guys I met while working in the past, but none of them really last. The flirtation on my side usually boils down to admittedly entertaining myself throughout the evening’s conundrum of 86s and asshole guests.

Any of these flirtations usually boil down to somewhere in between an unanswered text message and a maximum of a three-week relationship that could have definitely been capped at two weeks had I trusted my instincts.

In the time of COVID, the ante has been upped by mandatory face coverings for all employees. Listen, I would be lying if I said I didn’t enjoy the game of flirting with a mask on, using only my eyes to lure them in and get them to ask me out without ever having seen my face. It’s amazing. A few months ago I swore I had met Carrie Underwood’s husband’s twin. I simultaneously took an order at a table across the room while making eyes at him, which lead to him following me to the computer in order to get my number. Unfortunately, the head chef walked past as I was entering my digits in his phone and screamed, “Get it, Kaitlyn!” across the restaurant.

He texted me, and I answered in my Uber home, despite his initial text saying that I was a wonderful waitress (Tip #1: if you’re attempting to pick up your waitress, never compliment her waitressing skills. She doesn’t want to be a good waitress and she definitely doesn’t want to hear about how she’s a good waitress. Chances are she’s some type of artist that loathes her survival job, so get outta here with your waitressing compliments). He asked when I’d be available in the upcoming week to “grab a bite,” and I told him we’d have to wait until I got my schedule – when what I really meant was I need time to figure out a way to say,

“Um there’s a pandemic, and I actually like my lungs working at full capacity, so can we take a socially distanced walk instead?”

The next day I texted him to strike up casual conversation, and my “Happy Sunday! You a football fan?” text was left unanswered, so my problems were solved. This event is what led me to be even more impressed by my most recent approach.

I had a table of six guys that had been making jokes with me on and off all night. And I usually hate serving tables of men, because, well, men, but this was a fun, harmless group. I was standing in the far corner of the dining room as they began to make their exit. One of them started approaching me, and I felt an instant glitter of excitement.

“Hey, I know everything is complicated right now with COVID, so I’m just going to give you my number and you can decide what to do with it.”

I know that my shock showed in my response. “Oh! Thank you,” I said as I took the small, folded up paper from his hand while doing my best to show him I appreciated his approach. He nodded and walked off into the night.

I was absolutely touched that he even acknowledged that things are undoubtedly complicated right now. If dating in New York was difficult before, which it was, it’s now ten-fold. Hell, one hundred-fold. Ya can’t just go kissing strangers and drinking gin and tonics like ya used to. Like many other things this year, what used to be hard just got harder. I always felt like most dates were a waste of time, but now I’m risking my life for them, too? How bout just get me a petri dish for my eggs because I’m going to need several more years to figure this shit out. Count me out and Amazon Prime me a cat to start my collection with.

I admit he put me under a spell with his genuine approach, and I couldn’t help but shoot him a text (obviously after waiting the preliminary 24 hours just to make him sweat). I know, I know, I’m part of the problem… So I’ve heard.

Any who, we texted for a day or so before he made his advance: “Usually I’d engage in some more witty text banter, but I’m going to be more forward because I’m leaving the city for Thanksgiving. Any chance you’re free for a drink tomorrow or Tuesday?”

Ugh. Well, that was a fun day of socially distanced flirting but here’s where it ends, I told myself.  My response was honest but very blunt. “To be honest, I’m not really hanging out with people unless it’s outside and with a mask on,” I said, expecting to get some sort of attempt at persuasion back or just a total lack of interest. That’s why when he responded by being totally understanding and “down to play by my rules,” I couldn’t help but perk up.

With his work schedule and mine combined, along with the pressure of the upcoming holiday and constraints of the pandemic, we had an 11:00 a.m. coffee date in Washington Square Park in 26-degree weather. As fate would have it, it was the coldest day of the year so far. He still had not seen my face and I was attempting to wear lipstick under my mask, but I was becoming less confident as I walked to meet him and my snot ran into my KN95 from the blustery temps. Sexy.

We grabbed a coffee and walked to the park, carefully picking a bench in the sunlight to keep us a little warm. I knew as soon as I pulled my mask down to take a sip of my oat latte he was going to see my face for the first time, so I made a joke as I turned my head and wiped my snot on the back of my glove. We shared a bench but kept our masks on as we got to know each other.

It was honestly really refreshing to sit across from someone in the light of day and without the help of alcohol or the distraction of physical attraction. It was nice to know that this is as far as it would go for a while. There was no pressure to end the date with a kiss and certainly no shot at more than that.

We got approached by homeless men asking for money a few times, but only one offered a magic show. He was wearing a mask so we accepted. During his routine, he got a tiny bit too close to me and my date must’ve seen me lean back ever so slightly. He kindly asked the man to take back up a bit. It may seem like a small gesture but it went a hell of a long way in my book. I felt like someone other than myself was looking out for me, which is something that has barely happened this year.

In the past 10 grueling months I’ve lost some friends because of their irresponsible response to the virus. I’ve also grown closer and came to appreciate the friends that share my values.

The magician’s trick somehow revealed that I was 28 and he was 26 which was alarming to me. My general rule is to not look twice at any man under thirty. It is 2020, though, and I’ve had to break some old rules as well as come up with some new ones, so what the hell.

He also revealed that when he said he was going home for Thanksgiving (to Tampa) he would be staying there through the New Year, followed by a trip to the Grand Canyon for some hiking in early January. Our conversation continued for well over an hour before deciding to go for a stroll, which led to a pop-up shop, which led to picking up his lunch from Cava, and then dropping him off at his apartment on Houston.

He asked permission to hug me, which I surprised myself by allowing, and we said our goodbyes. “I don’t know how this works, but I had a really good time and I’d like to do it again?” “Same,” I responded while we both laughed at the uncertainty of it all.

On the hunt for new martini glasses, I slipped into Crate and Barrel. He had texted me before I even left the store and our witty text banter continued until the second week of December. And he must have sensed my uncertainty in what we were doing and ended things with me before I could do it with him. He sent me a full screen sized text message about his workload, the holidays, and the uncertainty of his return to New York anytime soon. And he said he’d text me when he gets back to the city, and I said the next cappuccino is on me.

I feel like I won’t hear from him again, and if I do, the cappuccino would have to be just a friendly cappuccino. I didn’t really feel a spark and felt like I couldn’t get past the age difference. That doesn’t negate how touched I was by his manners and respect to my boundaries. I really appreciated his genuine interest in getting to know me and make me feel safe. Funny enough, this was just four days over my average three-week relationship, so the end came right on schedule.

Regardless of the fact that our tryst didn’t end in either of us being swept off our feet, there is much to be learned from this experience.

Don’t be afraid to set boundaries: If someone is truly interested in you they will be willing to act within the confines of your comfort zone. If they’re not willing, they’re not worth it. If you’re getting involved with someone romantically it is crucial that you can be open about what you’re comfortable with.

That means with COVID and literally everything else. Boundaries are healthy, but you have to be willing to own them and speak them into existence. It may mean you lose some people, but those that stay truly respect you.

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About The Author

Kaitlyn-Renee Urban is an actor and writer with a passion for highlighting feminism in the arts. She hosts an IGTV show (coming January 2021) called “What We Know Now” centered around supporting local, women-run businesses while picking their brains for advice they’d give their younger selves. She lives in New York City, but it’s easier to find her on Instagram.

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