The City That Never Sleeps Sleeps Alone

The type of evening that cliché romantics are made of.

It was even raining.

And not the kind of rain where you get uncomfortably and unflatteringly drenched.

It was the ambiance-driven, pitter-patter kind of rain that is reflected on the sidewalks and decorates the lights.

Even I had to admit that it was lovely.

The loveliness of a summer night in New York.

So lovely that I felt in love, not with a person but with the city itself. The sidewalks, the puddles, the people walking through the puddles. You have to understand I love in LA where rain is not only an unwelcome, infrequent visitor, but a visitor that clashes with its own clichéd, beachy landscape.

But this night I was in love….So much so that when I started talking to a guy after a late night show who asked if I wanted to continue our banter over a drink across the street, I said, “Yes,” mostly because I didn’t want to end my date with NY. I didn’t want to say good-night to my favorite city.

So I went. I went across the street with this stranger from Long Island who was a beer connoisseur/musician (always the musician) where he picked me out an ale as we discussed our favorite music and books, particularly George Orwell’s, “1984” until 4am.

And then the most amazing thing happened.


We met. We chatted. We walked back to my hotel and I surprisingly didn’t have to give some ridiculous excuse about how tired I was or how I had to cut this evening, which somehow turned to morning, short, nor did I have to do that weird dance that one has to do when you’re trying to move away from someone.

‘I’d love to see you again. Call me when you’re back in town,’ he said.

And I thought about it. I thought about calling this great guy from NY, because truth be told I have been there since.

But I couldn’t do it.

I couldn’t be familiar when I wanted to remain a stranger.

A stranger who met another stranger in the city with pitter-patters and romantic clichés.

A stranger who met another stranger in New York.

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J is a happily single 30-something currently documenting her stories of love and loss. Her blog, “I Quit Dating” features excerpts of her journey as she reflects on the lessons learned from the men she loved. A complete collection of essays detailing her walk away from finding Mr. Right in order to pursue a more fulfilled life will be self-published next year. She recently moved from Los Angeles to New York. Contact: iquitdating (@)

8 thoughts on “The City That Never Sleeps Sleeps Alone”

  1. The one thing I miss about dating sometimes is the romance of those first few evenings out with someone when the chemistry is right. The thrill of flirtatious banter, the rush of discovery, the joy of finding yourself in synch with someone who suddenly makes you feel less alone in the world–when all these combine in the right setting, there are few things more magical.

    But I miss nothing about the heartbreak that always eventually followed for me. And I guess I like being free of heartbreak more than I miss those first dates!


  2. Sometimes a perfect night with a stranger should remain just that. It’s nice to have those memories, untarnished by trying to make it something more.


  3. I didn’t realize before(duh)that your in New York! It makes sense why you’d quit dating there. In my experience the dating scene there is pretty bad. I’d meet the prettiest women complaining about not being able to find(or keep)a guy! These were ladies that had it together too… I surmised there are so many beautiful woman there, that guys had overload and didn’t want to just pick one.
    a displaced New Yorker. 🙂


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