The Five Worst Dates I’ve Had in New York

Dating is hard. I don’t think it matters what city you’re in, what year it is, if you’re a male or female, or if you’re using dating apps or not. It’s just really fucking hard. Dating, or just basic romantic interaction, is the inspiration for blogs, TV shows, movies, songs. Businesses. This is because everyone finds it hard and wants to talk about how hard it is.

Some dates are great, and lead to love. Some are OK, and lead to nothing. Some are bad, and lead to funny stories.

When I first arrived in New York I dated a LOT. It was summer, I didn’t really know anyone, and I didn’t have a lot going on at work. It didn’t matter if I turned up on four hours of sleep, or hungover… or hungover and on four hours of sleep. These conditions are perfect for dating, and I organized dates all over Manhattan and Brooklyn in my first few months here.

These are the worst experiences I’ve had:

1. The “You’re Just Not Crazy Enough” Date
I met this guy in a cafe somewhere around Flatiron/Gramercy after work, off a 6 subway stop. Between telling me that I speak too quietly (fair point, probably, but maybe you should just… listen better?) and that he prefers Muay Thai to kickboxing, not that I asked, I found out he is divorced and has a stepson.

He quite clearly made up that he “forgot” about a comedy show “somewhere in Brooklyn” he’d planned to go to. I was relieved it was ending, but didn’t want to end up on the same subway.

This is how things went in my head:
Fuck. I’m going to Brooklyn too… I don’t want to be on the same subway. Find out where he’s going and pretend you’re not getting the same subway! Yes good plan Justine. OK.
Me: “So where in Brooklyn?”
Him: “Ummm Williamsburg I think.”
Damn it I’M going to Williamsburg. Ugh. OK.
Me: “Oh cool… which subway are you taking?”
Him: “Yeah, I just need to say that I don’t think this will work. You seem really smart and sweet but I need someone a bit more out there because I’m basically insane. So yeah I think we should just leave it there.”
Me: “Um OK. Bye.”

I need to give background. I had only just arrived in NY. I didn’t have close friends to talk to. Obviously, I had ways of talking to my friends in other places, but the fact I didn’t have anyone to go to immediately just made me really lonely.

I was also dealing with the end of something long term, so I wasn’t really in a place to handle public rejection. Everyone nearby heard what he had said, saw him shake his head to himself while he said it, and had to watch me walk out alone. Humiliating.
I did get a chance to tell him how I felt though:


2. The “I Forgot We’ve Already Met” Date
As I said, I went on a lot of dates in summer. I’m sure others did too. But, I hope I would remember if someone I had already met turned up again. I met this guy at a bar in Williamsburg.
He was really cool, a total unashamed, self-described lumberjack/hipster. He created his own little community in Williamsburg by drinking alone at bars and befriending the staff, even inviting them over for dinner. If that guy had liked me, I would have kept dating him. We had a good time, we did text a few times after to set something up but New York life kind of got in the way. I started using a different dating site and received a message from him. Same photos, same general bio, and same points in the first conversation.

“Oh, you’re Australian? That’s so cool, I love Australian music…” and so on.
We chatted back and forth and I mentioned a couple of bands who had recently played in New York, the same bands I’d mentioned on our first date, wondering if that would help his memory. It didn’t. He then asked for my phone number, and I had to say I’d known all along we’d already met and was playing to see how long it would take him to remember.

He seemed embarrassed, and we did go out twice after that, texted a little but then that was the end. The actual dates themselves were fun. I made friends with one of his friends at the bar we were at, and sang George Michael songs with her, and we went to two awesome shows. But it’s pretty embarrassing that someone didn’t remember me.

3. The “I’m Too Wasted to Stand Up So You Need to Send Me Home” Date
Ah, now this one was different. We’d already met, already been dating for a couple of weeks. He’d been watching football all day, I had been shopping around Park Slope and working on this blog. I started getting texts after the game had finished, a game I had thought would finish much later because fucking American football takes for FUCKING ever because this so-called “chess game” stops play every two seconds and people apparently aren’t capable of running more than a few meters at a time and they’re too fucking pussy to even be tackled properly and, I’m sorry… side issue. I miss Rugby League sometimes, OK?

Anyway. I said I wasn’t ready to meet yet, and still had to finish things and get ready to go out. I said not to come and meet me at the bar up the street from my house until I said so, because I didn’t want him to wait alone. He then texted 20 minutes later saying he was at the bar. I kept doing what I was doing, but skipped a couple of steps getting ready.

When I got to the bar he had befriended a couple. The woman was great, the man was not, and upon finding out I was Australian said he could name all the states (he couldn’t) and made a big deal about how we all eat Vegemite and own kangaroos or some shit. Meanwhile, the guy I was meeting was so drunk he couldn’t focus his eyes properly, couldn’t stand, (to be fair he’d injured his hip so it might have been partly that) and kept forgetting things I had said a minute before.

We left to go next door to another bar that had food, and he said I could go ahead while he finished his cigarette… even though the door was literally next to where he was standing and I’d said it was OK for me to wait outside with him. We got inside, he told me he was a “broken person” as an excuse for drinking too much while watching a football game, and I sent him home in an Uber we had to walk two blocks to get to because he’d put in the wrong location.

He sent me a text saying I’d “completely fucked him over… thanks” even though I hadn’t actually done anything. Did I end that dating experience then and there? No. It took him not giving me anything for Christmas (he wasn’t even Jewish) and then getting way too wasted and embarrassing me on NYE to end that one… I’m a slow learner.

4. The “I’m Sarcastic, Not a Dick. You Just Don’t Get Me” Date
I met a guy in the East Village, who proceeded to tell me how much better the Upper East Side is than anywhere else. Any time I would say anything about Williamsburg or even Brooklyn in general, he would make a snarky remark.
He challenged everything I said, continued to bring up Australian cliches like kangaroos (seriously Americans, you need to get over the kangaroo thing) and said there were no mosquitoes on the upper east side like there are in Williamsburg. Needless to say, there was no second date.

5. The “I’m Wearing a Fedora” Date
You know when you get an indication a date is going to be bad even before you go on it? Well, that’s what happened. We arranged to meet at IFC in the Village.
This guy worked for BAM and could get free tickets to movies. I was grateful for that of course. And by the end of the date I was grateful we’d been in a theater where you don’t have to talk for most of the night. I said I would meet him at the front of IFC and described what I was wearing.

I got this response:


We met, we watched the movie, we got on the F to Delancey to go to a bar called The Backroom. You might have heard about it.

On the subway, he asked if I went to art shows, and when I explained I have a very short attention span and often get bored at art galleries and exhibitions, he said that it’s important to really study paintings and art works to understand what the artist wanted to convey. This is probably true, but not something I’m terribly interested in tbh. The conversation wasn’t really going anywhere, he would ask questions, I would answer, and he would relate them back to himself.

The real kicker was when he said he’d read some of my reviews (I’d sent him links to my blog) and they were good, but when he writes reviews he likes to be ‘more academic, yet still accessible.’ I left soon after, we did not go home together and we did not see each other again.

I’ve been on good dates too, of course, but it’s fun to write about the bad ones. Even if a date is bad, you’ll get a good story out of it. I haven’t been on a date since old mate fedora… but don’t feel sorry for me. I like being on my own, and don’t need to fill my time with sub-par dates.

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Justine McNamara

I'm an Australian living in New York. I work in marketing but I write about music, New York, and my own personal experiences.

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