Dating : Working in The Dating Industry Could Not Prepare Me For The Challenges of Pandemic Dating

in partnership with @halfthestory

As a producer and co-host of NY-based live blind dating show, UpDating, I have spent most of my professional time curing everyone else’s romantic ambitions. By setting up strangers on blind dates in front of live audiences, I vicariously lived through their ups, downs, and excessive vodka tonic drink orders. My own dating life had always taken a back seat. When the pandemic hit and our live show paused, I actually became excited at the opportunity to focus on me.

That lasted for about two days. After all, how many times could I possibly watch Social Network, order sugar-free apple sauce, and FaceTime my grandmother? On the plus side, I gained a new appreciation for the constant companionship of my robotic vacuum, Roomba. On the downside, I felt more alone than ever before. It was time to figure out a way to “get back out there” in my own dating life — even though it was impossible to know what “there” even meant anymore.

I came to this epiphany — one I never thought I would realize — in a moment standing woefully on the balcony of my apartment, overlooking the Empire State Building, with Roomba by my side.

It had been two months since I had a first date. Six months since I made it to a third date. Two years since I had been in a relationship. I was actually lonely.

As an extrovert in the entertainment industry, I am a stranger on this distant planet Loneliness. A planet where you fall asleep, wake up, eat lunch, and double-dose on Natrol 10mg Melatonin…well, alone. A planet where you make small talk with Mario at the Green Leaf bodega about their new Chicken Caesar wrap even though you really don’t want to talk to Mario about any wrap at all.

I have been radically confused on how to meet someone romantically in this new world. When most of your dating prospects depart from New York City in the middle of a pandemic, you are left with extremely limited options for meeting a romantic partner. After striking out at during a Zoom Happy Hour, I turned back to an old nemesis: dating apps.

Dating apps and I had always had a toxic relationship. We had flirted occasionally but almost always ended up breaking up. As these are trying times, I left my stubbornness and ego at the door and downloaded Bumble, Raya, and Hinge (okay, I deleted and re-downloaded each app four times during the first 24 hours, but who’s counting?).

As the questions piled on from my early batch of matches, I quickly remembered why this was not my preferred method of meeting people.

“Omg, what is UpDating? Are you scouting for another dating app?”

No! It’s a show! This is for my own personal life. I try to separate the two.

“Hey! How are you?”

I’m good! But how about something a bit more substantive or thought-provoking?

“Hi! How are you holding up during quarantine?”

I’m not bad, but I’m not okay answering this for the 10,000th time.

After hours painstakingly tweaking my Hinge profile to project — I hoped — confident, quirky, sensitive me, the perseverance led to a Hinge match I was interested in. She was French, smart, successful, and responded to all of my failed in-app French attempts with the laughing emoji. After some brief dialogue around our favorite French films, she said: “How are you planning on impressing me?”

Followed by: “What do you do to seduce a woman?”

Now, those were messages I could rally behind. Bold. Direct. Provocative.

From there, we embarked on two walk, talk, and people-watch dates. We met by the New York version of the Arc de Triomphe, Washington Square Park, on our second date. It was one of those days where New York felt like New York again. Birds chirping, over-energetic street performers, and a wild pack of European tourists doing what they do best — stealthily enjoying a bottle of wine in the park. My date and I found a spot under a tree by the back of the fenced-in park, within sight of the clay-fitted restrooms. Within our field of vision, a couple lay enveloped in each other’s arms. We exchanged a judgmental eye roll, but I paused to wonder: why can’t that be us?

Despite my failed attempts at Franglish, we connected in multiple ways: getting into extended discussions around humanity, what it means to be alive, where we go when we die, places to travel — even dream weddings (in the South of France, naturally). With each passing topic, we held hands tighter — a forecast, one would imagine, of an end-of-date kiss to come.

In our previous lives, the internal debate as to how and when to go for the first kiss was never an easy mental exercise. Now, it seemed nearly impossible. Not willing to pass up my first human contact in weeks, I made a Hail Mary attempt at Franglish:

“How do you say kiss in French?”

“Un bisou.” She replied as I took a deep breath, and our first “bisou” unfolded under the starry, humid New York City skyline.

After date three in Brooklyn complete with late night pizza, she said “I like you.” I quickly followed suit.

Two days later, the conversation unexpectedly stalled, the Instagram DM’s faded, and our plans for the week ahead went unplanned. Hail Mary number two: a casual phone call to check-in and plan our next date.

She called me back a few minutes later to say: “your attentiveness to me is a bit much sometimes.”

In the sheer blink of an eye, the vibe had evaporated. Poof! Au Revoir! I was less upset about the situation as I was confused: what exactly did I do wrong?

Ok, I know my personality can be a bit much, but isn’t that just my truth?

Was it too aggressive for me to download Duolingo to learn some new phrases?

How about my joke about traveling to Brooklyn during COVID-19?! I actually do love Brooklyn!

“Well, I think I have my answer,” I responded to my friend, Olivia’s “any updates?” question earlier in the day. After firing off the text update, I locked my phone in my silverware drawer, and went out for a walk alone to my new favorite quarantine haunt, Madison Square Park. I started shaking my head, anxiously, as I walked down the street mouthing “the show goes on, I guess” to myself at least seven separate times (thankfully hidden by my mask).

Finding a bench, my optimistic and hopefully romantic brain imagined a storybook ending. An ending only Nora Ephron could imagine: the love of my life accidentally drops her tie-dye mask as I rush over to grab it for her. We giggle, exchange flirtatious pleasantries, and embark on a socially distanced walk through town. Within moments, we find an al fresco taqueria (it’s happy hour, naturally), where we share two margaritas and pomegranate guacamole. Within months, I drop to one knee in the exact location of our first meeting, with our family and photographers waiting around in the bushes.

Unfortunately, this imaginary soulmate failed to materialize. Instead, looking around, I saw a breakfast burrito stand sold out of every menu item. I noticed two city sanitation pickup trucks almost collide around the block. I even noticed another couple by a fountain across the bike path — this one sharing AirPods and feeding the pigeons. I checked my bench and observed that yes, I was still alone and my AirPods needed a charge.

Truth be told, I may have preferred ghosting. Sometimes, the infinite abyss of unanswered questions is slightly more bearable than one rigid answer about your entire existence. But it didn’t matter what I preferred; the rejection was complete.

For better or worse, I’m easing back into dating again. Fall is just around the corner, a vaccine (hopefully) in sight, and friends are miraculously reappearing in New York City. I call my new sense of romantic reality “purgatory” (okay, my therapist helped define this too — it’s a team effort).

Purgatory is a tricky beast in the midst of this chaotic world. I think of myself as that little squirrel in the movie Ice Age doomed to chase that acorn until I reach the beginning and end of Earth. Between Heaven and Hell. Love and loss. A butter croissant and starvation. A solo Lost in Translation viewing and running out of popcorn.

One thing helping me stay positive is the knowledge that I’m not alone in this anxious battle to avoid loneliness. According to the CDC, 47% of people under 30 reported feeling anxious during July. I’m going to go out on a limb and bet if we drill into that under 30 category with a focus on just single people, we’ll see that number skyrocket.

Despite some marginal success on the apps, I remain mostly confused about what happens next in the world of dating. But ever optimistic.

We always had to catch lightning in a bottle when it came to finding someone. Every single star does have to align. Navigating single life during the pandemic has turned into searching for a well in the middle of summer in the Mojave Desert. I think we can safely say the journey for lightning-in-a-bottle love has lowered its standards into I-just-don’t-want-to-sit-on-this-Madison-Square-Park-bench-alone. Do you want to join?