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Part 22: Dating, In The City That Never Sleeps.

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My therapist predicted I’d date three guys at once. He said that I’d stay out late and fall out of cabs.

“It’s a natural reaction after a breakup,” he explained, “especially for a newly single girl who just moved to Manhattan.”

Beyond hyperbole, I knew he was attempting to position my situation in a more favorable light which at the time I saw as being overwhelming, sad, and, in terms of my tiny new place, somewhat depressing.

Seriously though, three guys at once?

“Yes,” he insisted. “It’s safe to assume that any pretty girl living in Manhattan has at least three guys in rotation.” He wagged his pen at me with a particular emphasis on the last four words.

I sighed and flopped backwards into an overstuffed cushion. This scenario was exhausting.

In the past two years of living in New York, I had naturally acquired the trait that defaulted to, and even sought out to be, utterly jaded and cynical about mostly everything – especially dating.

Yet it happened. After the great Breakup of 2014, I left the glorious loft in Williamsburg for a tiny apartment in SoHo. What was formerly our place had become simply…mine.

And right before the move, it began. What I thought to be a new relationship had begun.

My friends informed me gently that this was in fact called a rebound. At our next session, my therapist shook his head, mentioned the word “distraction,” and made a joke about calling up his old pal Ryan Gosling.

Everyone was right. In fact, trying to define the whole thing left me more exhausted than the actual act of putting in real effort to make it work.

What did I do wrong? This wasn’t the first time I didn’t understand a cultural norm that, in retrospect, should’ve been so clear from the beginning.

Back in Los Angeles, I had a friend I met once a month for dinner. Let’s call him Anthony.

Anthony is a massive foodie. When I announced over dinner at Cha-Cha Chicken that I was moving to New York, he magically produced a pen and began jotting down restaurant names on a napkin. I asked him what the big deal was, and he openly gasped at my ignorance.

He shook his head with gusto and proceeded to launch into a lengthy diatribe about the significance of restaurant culture in the Big Apple.

“Think of it this way,” he said, wagging the pen at me.

“Eating in New York City is a sport. It’s competitive. Most New Yorkers obsess over the Times’ Food section like everyone else in America does over the NFL.”

I nodded slowly, picking at my kale.

“You have to stay on top of the openings if you want any common ground with these people. You’ve gotta know about all the new spots, the chefs, and the trends. Learn to speak the language, and you’ll learn about good food. You will never eat so well in your life.”

Perhaps the culture of dating functions in a similar way with an ongoing stream of activity and corresponding flow of people to meet.

Keeping up with restaurants? I could do that. It’s more passive than anything else; all I had to do was follow a couple of blogs and I’d be set. But dating?

I learned quickly that the feat my therapist described is, in fact, possible if treated in a similarly passive way.

Let me explain.

As it is widely known, a lot can happen in a New York City day.

It is, in theory, possible to meet someone at an after-work event, exchange friendly banter then eventually say goodbye, only to randomly run into each other twenty minutes later downstairs waiting for the subway.

He may or may not invite you to a party. Since you have nothing else to do (except go home and order Seamless then fuss over work e-mails some more), you smile and say yes.

You travel a few more stops on the subway. You dance all night, meet more interesting people, have some laughs, and compare weekend plans.

He walks you all the way home from the Lower East Side and kisses you at the door.

You tell him, in truth, that you had a great time.

Wait — rewind. Who is this person? And was this a date or mere Manhattan happenstance?

In your mind, the two of you have definitely gone out on a date. Or was this a hang? Was it a date or a hang?!

It’s been six hours that will turn into a text conversation the next day, which will lead to another date, then a kissing session on Mercer Street with an eventual fade-out where you ultimately remain friends with no hard feelings.

This model is simultaneously applied to other people, and how liberal one wants to get in one’s layering corresponds directly to not only how much time he or she has on their hands but how much effort they’re willing to provide for each scenario.

What happens next? Well, I wouldn’t say that I went on a tear. In my defense, I didn’t even want to be dating in the first place. It simply covered the bruises that were a direct result of the Breakup of 2014.

Dating got me out of the house again. It threw me into the center of Manhattan, a.k.a. the Center of the Universe.

Becoming increasingly social took my mind off the breakup. It also kept me distracted from the additional stressors of everyday life.

There was the guy I stayed up all night with, talking and sipping good scotch. We listened to old soul records and philosophized until dawn.

There was another I met at a friend’s birthday party. We met for brunch only to wind up spending the entire weekend together. I experienced what it was like — for the first time in a long time — to feel desired and appreciated and possibly even adored.

There were moments during some of these conversations where I felt hope.

I felt hope in the goodness of people. I once again believed in the idea that I could live the life I’ve always secretly dreamed of living. For the first time in a long time, I believed I was lovable.

Don’t get me wrong. That cynical New Yorker was still along for the ride not only in my mind but in the minds of those I was spending time with. We were being cynical together about the world around us and in the reality of what the next day would bring.

The grind and hustle paired with the possibilities of what we ultimately want to achieve one day gets in the way of building anything remotely substantial. It clouds our vision, making us single-minded and hungry, adventurous yet starved.

We live in a world where the present and future constantly collide, where reality and the shiny figments of our imagination struggle to co-exist.

So, you see each other when it’s convenient. Lots of schedule comparing is involved.

You equally seek traits to adore along with possible red flags that give you an excuse to run.

And eventually, you both move on, perhaps not only to the next person, but to the next opportunity to see ourselves through the lens of someone else’s vision.

The most authentic version of ourselves is always the project that requires the most love and understanding. While it extends to others we know and trust, this love is already spread thin.

Putting in that kind of work needs to build and evolve over time. And on an island already overcrowded with the overly-entitled and eagerly ambitious, there is simply no time.

I don’t mean to be overly cynical.

Maybe it is possible to enjoy a slow burn while we’re busy being ambitious — a quick text as we dash to our next meeting, a brief phone call in between getting in and out of cabs, a meeting rescheduled to grab a late-afternoon coffee.

Perhaps the substance of a real relationship runs current-like beneath the city like the subway, waiting for the right time and place to emerge.

It’s a lingering supper at a restaurant far from trendy.

Despite what everyone else says, I still think about that first person who may have counted. I’ve known him for a while and hope to know him forever. We were both too preoccupied with being busy and had too much to figure out as individuals.

I needed to understand that in that situation, there were no hard feelings. Timing and presence played a key role as we moved along, either forward into our respective futures or simply past something that had hurt.

It may never be the right time, but this will always be our New York.