Real stories about dating and relationships in New York City. Truth is more interesting than fiction.

The Surreal Nature of Dating in the City

 The Surreal Nature of Dating in the City guest posts  Ah, dating in .  What a beautiful disaster. Today’s dating adventure is from Jennifer Gargotto is the creator of MsMorphosis. She, also recently wrote her first ebook, Navigating Dating: A Single Woman’s Guide to Dating Without Losing Herself.

 The Surreal Nature of Dating in the City

I lived in New York City for exactly 6 months while I was studying journalism at NYU.

It was, without a doubt, the most surreal experience of my life – but in no way more so than in dating.

Back in Colorado, I had always had a rich dating life. I had always dated a lot, believing that finding love is a numbers game, so naturally I was equally adventurous when I got to the city. But looking for companionship in the loneliest city in the world (right after, I might add, my first real relationship was ended via a changed Facebook status) was a whole new ballgame. It’s a lot to condense, but here’s what I’ve got.

The first guy I met found me in line during some sort of school orientation situation. He was a few years older, and a physics major. He was also a club promoter, and wanted to take me out. Since I was underage, the idea of being able to get in anywhere was exciting. In Colorado I would have shied away from something so forward, but here I was lonely and out of options. I agreed.

He was a good looking guy, incredibly smart, with lots of connections. For some reason he was enamored with me. He wanted to date. He didn’t seem, to me, like the kind of guy that could ever settle down. I didn’t trust it, and never really gave him a chance. Years later I still wondered if he was the one that got away. I went out and spent a weekend with him in New York. He was wonderful, as wonderful as I remembered, but he wasn’t for me. He wasn’t the one that got away. But that taught me my first big underage lesson: you’ll never get over something that seems to good to be true until you give it a chance.

The second guy was also older. He was a teacher’s assistant for a French class right by my world lit class, and we eventually ran into each other enough that we started talking. The thing about this TA, though, was that he was rich. I’ve never cared about how much money a guy had until I was living in New York City. Stuck in my shared studio that smelled like curry and had the ambiance of a mental hospital, I was suddenly really open to finding a way to make it work with the TA living in a gorgeously furnished 4-bedroom.

There’s nothing half-assed about New York.

He couldn’t just be rich, he also had to know Kate Moss, have a private island, and enough drugs in his apartment to fuel his good friend Kate Moss for a lifetime.

It was too much for me. Eventually I realized I liked sitting in my mental house of an apartment more than the nice dinners, even though I really, really wanted to get to appreciate the nice restaurants in New York. And guess what? When I was with him I could eat at the amazing restaurants. But eventually I lost my appetite. When I left New York, I didn’t even let him know. And that was the second lesson I learned: Even when you’re in the loneliest city in the world, missing out on some of the greatest meals in the world because it also happens to be the most expensive city in the world, money still can’t make you fall for someone that isn’t right for you.

The third one was a different story. This one, I really liked. He wasn’t that great looking, but the way he dressed reminded me of home. The guys in New York are really, really metro compared to Boulder and Denver. I’m used to beer drinking, t-shirt wearing, shaggy-haired men. The tight jeans and martinis (on them, not me) were really starting to get to me, and I was really starting to crave home.

Anyways, I think his name was Taylor. I’m not sure how I got him to ask me out, but eventually he did. We went out, and I thought it was a great date. We got sushi. We sat at a wine bar and talked. I went home happy. Finally I had met someone I liked.

The next day in class he sat at the opposite end of the room.

He didn’t talk to me for days. Didn’t call. Nothing.

Finally, I sent him a message asking him what was up. He wrote back and said “I’m just not into you, can you get that?”

That was the whole message.

I cried for a second, but quickly I realized it wasn’t worth it. He was mean. I didn’t know why he didn’t like me, but it didn’t matter. The only thing I really liked about him anyways was that he reminded me of home. So that was when I knew what I had to do: it was time to come home.


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5 to “The Surreal Nature of Dating in the City”


  1. Sarah says:

    Trust me, I completely understand! One time I met this guy who lived on the westside, and I completely fell HEAD over heels. But then shortly after I realized I wasn’t his only suitor. Bummer

  2. Jennifer says:

    Haha Thank you for commenting.. that actually DOES make me feel better! :)
    Jennifer recently posted..A Letter to the Haters: Why I Support Kony 2012My Profile

  3. Onely says:

    Oh wow, that was really mean of the text guy. Also, very insecure–not that knowing that helps much. = )

    You got some great stories out of the Kate Moss guy though, I’m sure. That’s what I try to do in adverse circumstances, think of it as sort of literary constructs in a novel–or a horror movie, what have you. = )

    CC
    Onely recently posted..STFU Glenn Grothman, or Should We Say–Glenn Gross, Man.My Profile

  4. Katie Martin says:

    I haven’t dated a whole lot, but I can understand the striving to get out there and find a person who you really click with. I especially appreciate your experience with the first guy you mentioned. I had a very similar relationship, and sometimes I still wonder if I made a mistake ending it, but I feel like I still know in my heart he just wasn’t who I wanted to end up with, even though he was a great guy. It can be a pain to find someone who technically fills so many of your “check marks” and yet you know they still aren’t right for you. But trusting your gut is so important, and obviously you are doing that! I wonder, did it get better once you got back to Colorado?

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