Hustle Dating — An account of NYC relationships as a single girl in her 20's
I am a serial dater.
No, I have no shame in saying it…or writing it. From the countless number of meet-ups and hookups and fuckups that I’ve put myself through…I am starting to wonder what my real intentions are.
Do I want to find love, or do I crave the spark of possibility that ignites when I meet someone new?
Dating is really tough in NYC.
I feel the need to always keep my options open, and one way of ensuring that is by going on my weekly dates. I often aim for around 2 or 3 per week and rarely see the person more than twice. And no, this isn’t some sadistic habit that I want to keep, I just find it easiest to maintain some sense of sanity this way. I’ve come to realize that people don’t become attached in NYC. They cling to their rent-stabilized apartments more than a stable relationship. And honestly, I get it. As I said, it’s tough dating in NYC.
I guess I should share a few of my dating history gems to provide credibility to what I’m claiming.
Rick Owens collector. Recovering alcoholic. Major mommy issues. Paid over $300 to get hair done in a specific Japanese style to look EXACTLY like Rick Owens. Believed he would be sleeping over on the first date…like…planned ahead to do this. Was on the keto diet for months and was terrified to get off of it. Only spoke about his recovery process (which was good for him and I’m happy he was doing well), but god dammit do you have ANYTHING ELSE TO DISCUSS? We stopped speaking after I asked him if he was seeing other people and he went off on me for being too clingy.
Long Island Italian American man child. 31. 3 roommates. Dirty. Commitment issues. I opened up to this man about my sexual issues/traumas and why it was hard for me to be intimate and this man goes: “You should get that figured out”. He then proceeds to mention how he missed the passionate sex he and his ex would have. I was sitting half naked on my bed already emotionally rocked from what he had just said to me…and then he said that shit.
He was upset that I wasn’t the horny little 23 year old he was hoping for. Remember this man was 31 and had 3 roommates…in Long Island. Was I staying with this guy for some strange validation because he was hot? Did I like that he was older? In any case, not a fan.
Egyptian mafia man. I say mafia but I genuinely have no idea what this man’s occupation was. Wouldn’t tell me what he did for work. All I knew was that he…in his words: “Made enough money to take care of me and my mother forever”.
Get Isis O’Flynn-Shahaf’s stories in your inbox
Join Medium for free to get updates from this writer.
Ok sir, settle down.
Not gonna lie, that had me though. As much as it freaked me out I was genuinely intrigued. Don’t judge me, you would have been the same. He picked me up in a fancy Mercedes and was 6’6. Although he was very beautiful, romantic, and polite, he had some questionable things to say.
He asked me if I would convert to being Muslim and if I would be a housewife for the rest of my life. He told me that his wife would never interact with other men and that the “jobs” she would have would only let her be around other women (babysitting, pet sitting, cleaning, etc). He said he didn’t listen to music (especially in the morning) because it distracted him from being with his thoughts. He said he only trusted logic and reason.
He told me I looked like a movie star and then I never heard from him again.
Except for when he liked my profile on Hinge (we originally met on tinder) and then immediately unmatched.
One of the funnier ones was this kid who was starting his first year at NYU. He was originally from Ohio so the city was VERY exciting for him.
We met at a bar late at night and he ordered an ice cream sundae. That’s it. Whilst engaging with said sundae, this man proceeded to tell me his love for ketamine. He mentioned how he frequently took this drug and loved all things adrenaline. I started to question at what point does a date become a babysitting gig?
I used to be so concerned about whether or not my date was going to like me. Now it’s become the luck of the draw for whether or not I’ll meet the love of my life or the mad hatter from Alice in Wonderland.
But honestly, it’s hard to even imagine wanting to find love when everyone else seems to be in polyamorous or sexually explorational relationships. What does dating even mean in NYC?
Is it just casually meeting up once in a while to get drinks, Italian food, and a shag? Is it having someone be your plus one at a wedding but never having them see your childhood stuffed animal? Is it being so totally head over heels for someone you’ve been seeing for a few months only to find out they never wanted anything serious and thought you guys were just casual?
Whatever it is, I’m a sad but continuous participant in the rat race of the rat city of the world to find love…or the Jekyll to my Hyde.
