My Ridiculous Dating System Totally Works!

There’s just one catch.,


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Last year, in the middle of the pandemic, I appeared as a guest on a (now-defunct) dating show. With cameras rolling, I sat on a teal couch next to the show’s host, who had prepped for an interview with a man who is neurotic about dating — a man who composes spreadsheets of relationship stages and lists of traits of potential dates.

That man is me. It’s who I am and what I do. In the host’s mind, my neurosis was bad. In mine, it was good. So good, in fact, that I recently had met a guy I liked and could see a future with.

“So, Alex,” she said. “How’s your love life?”

“I just started dating a boy,” I said. “So, it’s great.”

Her face soured and she touched her earpiece. Clearly my answer was not the one she was expecting.

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; I had crazy lists of dating requirements that they assumed came from my deep fear of commitment, as if I were sabotaging myself with a system that would exclude nearly everyone.

They assumed wrong.

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I have many fears: inadequacy, coming across as desperate, running into the guy from the bus in 5th grade who told me I had “woman hips.” But fear of commitment? No. Nevertheless, I wasn’t about to fight the producer and host whose show I wanted to be on.

They were right about one thing, though. I am indeed an incredible list maker. I create dating checklists and processes that are measured with tools and data. Little tidbits of information that encourage me to keep paddling through a sea of potential boyfriends 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 else each of them could have been.

I began my system seven years ago on Trello, the project management software I use at work. I simply had endured one too many bad first dates. The Hinge guy who may have used his son’s photos as his own. The lawyer whose coming-out story was somehow less interesting than his love of tailored suits. The finance bro who thought it was weird that I was Jewish while blonde.

I experienced repeated collisions of misaligned values and discovered personality traits I wanted to avoid. Dates that caused me to be versions of myself I didn’t like and cost me time that I could have spent on my couch: just me, a Vicodin and a book about sadness.

To break this cycle, I decided to track it all. Make sense of the patterns and change them.

Cue the Trello board. As of today, the board has six stages and eight traits. It’s similar to the business development process of a salesperson, with each stage representing a step toward a successful deal and each trait representing a characteristic that is more likely to lead to 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, his card progresses from left to right, passing through these stages until we’re dating. If we never get that far, I archive his card, in which case an archived card is all he will ever be.

I evaluate my potential dates based on eight traits. Five of those traits I try to learn about before the date. The remaining three I think about after the date.

Before the first date, I try to determine the following: Does he make me laugh via text? Does he live in LA? Does he like his job? Is he down to go backpacking? Will he get on the phone?

After the first date, I ask myself: Does he like himself? Is he curious? Is he kind?

It’s a little crazy, imperfect and, yes, judgmental. My systematic approach may well be weeding out someone who could make me my happiest self. But the leaving-it-up-to-fate alternative of relying on chemistry, physical attraction and serendipity haven’t led me to that person either.

I would prefer to have something to work on. Tasks to do and cards to sort, as opposed to waiting around in Whole Foods for some dude and me to magically lock eyes as we 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 has 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.

But that’s not what they wanted me to talk about. They didn’t like my traits. For 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 you hate even more. Someone you get angry at for how he rolls up the toothpaste tube or doesn’t refill the Brita.

Back in the studio, it was time to reshoot the scene with me embracing my too-neurotic-to-ever-find-love persona, so viewers at home could see me as a cautionary tale, an exaggeration, perhaps, of their own neuroses.

On that teal couch, with my hands shaking, I stared at the dating host as she hit me with her questions.

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

“Wow,” I said. “I never thought of that.”

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

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

She smiled. “Now go out there and be more open minded. Let people in. You have so much to offer.” Then she turned to the camera and said, “You all have so much to offer. Open your hearts and minds and be yourselves. And thanks for watching.”

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 seemed 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 will look at my Trello board with names like “Mark Emojitexter” and “DavidWeirdCat” and accept that I don’t know that my methods work any more than the reality show people knew how I, “AlexNeuroticDater,” would fare on an episode of their show.

I think back to the guy I was happily dating then. The one I spoke about while sitting on that teal couch. With his great smile and perfect score of eight out of eight traits. The guy I’m no longer dating.

Why didn’t it work out?

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.

Alex Kruger is a business and comedy writer who lives in Los Angeles.

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