Dating in New York City (Part 2)

I decided to share another round of my first date stories after Time Out came out with the news that NYC is the best city in the world to find your soul mate. Green spaces, coffee shops and romantic restaurants might set the mood but here’s the reality. Click here for Part 1.


I first saw my date when he walked off the L line stop. We walked together separately until we reached the restaurant and then said “oh, it’s you” and introduced ourselves. Cringe. We sat down and he looked at his phone. I figured he was looking at the menu. He said he might have to work and took three separate calls over the course of two hours. He admitted it was a good thing because I would know what I was getting myself into if we decided to be in a relationship. I didn’t feel a spark so we had bigger problems than his work life balance. I do hope he gets his promotion though!

My next date was at a cozy restaurant I had been dying to go to. The scene was set, he was very attractive and all we needed was a decent conversation. Turns out he didn’t have much to say. He knew nothing about current events or local politics. For example, he said his favorite sport was golfing. I followed up with “How do you feel about the LIV golf tour?” as thats been top of the news for months. He had no idea. He also didn’t know any NYC news and nothing about his neighborhood. But really the nail in the coffin was when he said he didn’t “feel the need” to travel and had only been out of the country once.

I was catfished by a pilot that lived in the area. He looked nothing like his Bumble photos but it was just a coffee meet-up so I didn’t mention it. I spent the whole time grilling him on life as a pilot, his travel destinations and covid precautions etc. (Did you know pilots never had to be tested or quarantine after trips?) I wasn’t sure if he liked me but then he asked for my phone number. I awkwardly hesitated before giving him my digits. Pilot 100% noticed and I never heard from him again. Maybe he’s updated his photos since then.

Recently I bonded with a Williamsburg man over our love for 90s hits (which is on my profile). He seemed fun and flirty so I asked if he wanted to get a drink in the area. I chose an old pub with great vibes on Berry Street. I got there first and was given a corner booth, inside but with the windows open. I was serenaded by an amazing a cappella group wondering the street. It was the perfect date….and then he showed up. He’s the guy who doesn’t ask questions. We all know one. Because of this, our conversation didn’t flow and I found myself struggling to come up with topics. I did learn some fun facts: did you know the very first ice cream made was with tomatoes? Always find a takeaway from the date!

I said yes to a date with a man who declared he knew of me, but wouldn’t tell me how. Maybe his way of reeling me in? On a chilly night over the winter, he got to the restaurant first but didn’t tell me. When I found him, he said he was relieved he had not been catfished. Thanks? Then he chose a table outside (without consulting me) even though the cute bar area was much more inviting. We sat down and he proceeds to tell me about our mutual connection, my ex-boyfriend. We’re 10 minutes into the conversation focused around my ex and I don’t even have a drink yet. Does he know how to date? Turns out, he had broken off his five year engagement two months prior. So no, he didn’t. He insisted he wanted a relationship now, but didn’t know where he would be living or the type of person he was looking for. You might want to take a second, buddy.

Right out of the gate, this guy came in hot. He gave me a big bear hug and told me I looked amazing. We sat at a nice table and ordered wine, which he raved about. We spoke about our upcoming trips, most of which happened to be wedding related. By the end of the date I had been invited to golf, a wedding and a beach trip. We walked out of the restaurant with his arm was around me and he was ready to make his move: which was another glass of wine at his place that happened to be around the corner. I didn’t go, but I did appreciate his enthusiasm.

This was a case of two Hinge identities. The first was a clean shaven man in a suit and the second was a long haired man playing the guitar. I have to admit I was intrigued. Which one would show up? Turns out it was the second. He owned a music venue in town and had a very interesting background. One of which, was that he was married for several years and had two children. He said I was his first ever dating app date. It was pleasant enough conversation. I also gave him some app profile tips. At the end of the date, I asked him how it went. He said “That wasn’t so scary! Maybe I’ll go on another one.” Godspeed music man!

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