The dating board article [NYTimes]

A modified version of this piece appeared in The New York Times

That Time I Was On A Reality TV Show For Being Bad At Dating 

Last year, in the middle of the pandemic, I appeared as a dating show guest on a now-defunct streaming service.

With cameras rolling, I sat on a teal couch next to a dating influencer named Megan, a woman so TV-Pretty that when people look at her they probably feel themselves lost in her eyes, which means that when I look at her, I feel myself lost in shame.

“So, Alex. How’s your lovelife?” she asked.

“I just started dating a guy! So it’s really good!” I said, proudly. 

Megan’s face soured. She touched her earpiece and listened. Something about my answer not being the right one. 

Out walked the producer wearing her “I’m important” headset. She was the type of person who obviously excelled at her job — a job that I was making difficult.

She explained that my love life wasn’t supposed to be good. The reason they brought me on the show is because my standards were too high. My crazy list of dating requirements had created a self-sabotaging system that excluded nearly everyone and that it all stemmed from my deep fear of commitment.

I don’t agree.

I have many fears. Inadequacy, body dysmorphia, running into the guy from the bus in fifth grade who told me I had womanhips (he’s right), but fear of commitment? No. Nevertheless, I wasn’t about to fight the producer, whose show I wanted to be on. No need to let my ego get in the way of success.

She was right though. I am an incredible listmaker. Dating checklists and processes measured with tools and data. Little tidbits of information that encourage me to keep paddling through a sea of boyfriends, all the while preventing me from docking my ship on a mediocre “good-enough” relationship. A relationship similar to that of so many couples I know, filled with silent meals, wandering eyes and forlorn regrets of what each of them could have been.

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It began 7 years ago, my system. I built it with a project management software called Trello, following too many bad first dates. Dates that caused me to be versions of myself I didn’t want to be. The date with the Hinge guy who maybe used his son’s photos as his own. The boring lawyer – his coming-out-story somehow less interesting than his love of custom tailored suits.  Or the racist finance bro, who thought it was weird that I was Jewish while blonde.

“It’s the only reason my family made it through the Holocaust. The only reason I’m still here”, I joked and waited for laughter. 

It never came.  

Collisions of misaligned values and nuanced dialogue unnoticed. Things I wanted to avoid.

And so I started to track it all. Wasteful dates that I’d rather replace with a happy night alone on my couch. Me, myself, and a vicodin, coupled with some book about sadness. 

Cue: Trello board. As of today, the board has six “stages” and eight “traits”. It’s similar to the business development process of a salesperson, each stage representing a step towards a successful deal, each trait representing a characteristic that is more likely to lead to said success. 

The stages are: To Vet, Vetting, Vetted, Scheduling, Scheduled and Dating. Each person is represented by a Trello card — a kind of digital sticky note.

Before I go on a date with anyone, their card progresses from left to right, passing through these stages until we’re dating. If we never get that far, I archive their card, in which case an archived card is all they’ll ever be.

For the traits there are two two categories: traits I try to vet for before the date, and traits I vet for afterwards

Before the first date I try to determine the following: Do they make me laugh via text? Do they live in L.A.? Do they like their job? Are they down to go backpacking? Will they get on the phone?

After the first date, I ask myself: Do they like themselves? Are they curious? Are they kind?

It’s a little crazy, imperfect, and at times, judgmental. It might weed out outliers who could make me my happiest self. False negatives. But the alternative “up-to-fate” lovelife, is something that I fear would be much worse – one in which I’m supposed to believe in the off-chance that I’ll be standing at a Whole Foods and an attractive vers-bottom and I will reach for the same carton of oat milk.

So far, my Trello system has worked, or at least that’s what I tell myself. It’s led me to more than enough moments of lying happily next to someone and forgetting about my inbox, of looking at someone and knowing that I’m growing in ways that matter to me, and believing, regardless of his Trello card’s longevity, that lying there with him was a good use of my time.

That’s how I originally pitched myself to the show — as someone who believed in my system. “The only reason any of my boyfriends have been boyfriends at all is because they had at least six out of eight traits,” I had said on a Zoom call with the casting manager.

“That’s great Alex. But let’s try and find other traits to talk about.” 

You see, for TV, the traits I listed are boring. TV traits need to be sexy: face, abs, and girth. Traits that eventually fade, and leave you with a partner you hate and a version of yourself that you hate even more. Someone who you get mad at for how they roll up the toothpaste or don’t fill up the Brita – distractions for a failing relationship where you each don’t like the person the other wants to be.

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Back in the studio, it was time to reshoot the scene with my newfound illustrated-as-tragic dating life where people back home would see hyperboles of their own problems lived out by yours truly. 

So on that teal couch I sat, my hands shaking as I stared at the incredibly charming Megan who was about to hit me with questions made of bait for which there were no good answers.

“Alex, I think the reason you’re alone is because you have too many high standards. What do you think of that?” she said.

“Wow. No. I’ve never thought of that before,” I said, submitting.

“You can’t expect someone to check that many boxes that quickly,” she continued. “And if you’re so busy vetting, you’re probably not checking their boxes.”

“Wow. That makes sense. You’re probably right,” I said.

She smiled. “Now go out there and be more open-minded. Let people in. You have so much to offer!”

She turned to look directly at the camera, talking to the audience back home, “You all have so much to offer! Open your hearts and minds and be yourself! And thanks for watching. See you all next Wednesday at 5pm Pacific!”

A live-laugh-love moment of unscripted television. 

She exhaled and turned to me. “Great meeting you, Alex. And I am so happy that your dating life is going well. Good luck with that guy.” Her words were kind and genuine. She winked as she walked out, having gotten from me what she was looking for, as if she had funneled me through her own little Trello board.

As I sat there, consensually gaslit, I thought about her made-for-TV advice. About how my system has created a method full of swift left-swipes — a system that, if continued, may lead me to a life alone as a single gay man, perhaps finding social validation as a second assistant coach on an intramural L.G.B.T.Q. kickball team, someone who refers to his dogs as his kids and who doesn’t believe in settling down because doing so would imply that he believes in something at which he has completely failed.

But I’m not there yet. And as of today, I hate kickball.

For now, I’ll look at my Trello board with names like “Mark Emojitexter” and “DavidWeirdCat” and accept that I don’t know that any of it works any more than a casting manager for a dating show knows that “AlexNeuroticDater” will fare well on an episode. 

I think back to the guy I was happily dating then. The one I spoke about while sitting with Megan on that teal couch. With his great smile and perfect score of eight out of eight traits. 

I think back about why it didn’t work out.

And I think it’s because he didn’t like me back.

Well then. “Does he like me back?”

A ninth trait to add to the board.

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My next piece will be about doing Ayahuasca.

It sucked.

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