Dating in NYC: The Men You’ll Meet

Before I moved to the city, I was a semi-serial monogamist. I was in relationships on and off since I was 14. Although I was used to keeping steady relationships throughout my teenage years, I was more than happy to head into my new life in NYC single as a Pringle.

Since I moved here in 2016, I have gone on countless dates. Some have turned into second or third dates, some I’ve formed temporary “relationships” with, and some I’ve rightfully ghosted (not sorry). I tend to go on one or two dates a month, primarily to keep myself motivated and active in the dating scene. 

Everyone has different reasons why they date. Personally, I’m not looking for a relationship but if something felt right, I would go for it. Obviously, that has not happened as I am still 110% single, but I’m perfectly okay with that because frankly, I love being single. I’ve been able to build immense love for myself over the years by learning how to be alone. I still have a lot of work to do on myself, but I am happy with who I am.

To preface, I do not have a “type”. I’ve dated endless types of men of various ages, backgrounds, personalities, etc. Yes, there are characteristics I’d love to see in the men that I date, both physically and personality-wise, but I tend to give everyone a chance if my intuition gives me a thumbs up. 

Below I’ve compiled a list of men you’ll date in NYC (aka, that I’ve dated). So you are aware, I met all these men on dating apps like Hinge and Bumble. These experiences are my own but who knows, maybe you’ve dated similar men as well and can relate to these stories.

As a disclaimer, some of these men were straight-up jokes, while others I took a little more seriously. All in all, I’m happy to have met all of them because they each taught me valuable lessons about what I want, and don’t want, in a potential partner. 

I’d love to hear about your experiences dating in the city and if you’ve dated these types of men as well. Who knows, maybe we’re Eskimo sisters!

1. The Polite Playboy

Who is he:
A 30 something-year-old with a 20 something mindset. He works at a finance startup, loves to say “bruh”, and always has a half-empty Four Loko in his fridge.

Where you could find him on the weekends:
Bar hopping at all his favorite dive bars with his friends from his old college fraternity. Yup. College fraternity.

Your first date:
He asks to meet at a dive bar (cringe), but you agree. You chit chat for a few hours and it seems like he’s into you. He asks stimulating questions, is polite, pays for your drinks. You get no bad vibes, although you can tell he is slightly immature. It wasn’t a revolutionary date, but it was good. 7/10. 

The relationship:
He checks up on you a few times a week, and you go get drinks a few more times. You both agree to keep things casual and before you know it, the dinner and drinks end and you are spending all your time together at each other’s apartments. This gets old incredibly fast because although it is a casual relationship, you still enjoy doing things outside of Netflix and Chill every time you see him. However, he is surprisingly smart, and you enjoy analyzing the wonders of the world with him. But you always keep in the back of your mind that this relationship is temporary. 

Why it didn’t work out:
Although he is fun and you enjoy your time together, he is a textbook fuckboy. The relationship no longer benefits you past a certain point, you get bored and you eventually say BUH BYE (but no hard feelings). 

2. The “Model” Bartender

Who is he:
Late 20’s guy with a moderately chiseled jawline and ken doll body who is a self-proclaimed “model” that did a few photoshoots for Spirit Halloween back in 2015. He has 20k followers on Instagram and a completely black and white feed featuring only shirtless (and sometimes pantless) pictures.

Where you could find him on the weekends:
Working at the local bar, staring at himself in the mirror located behind the liquor and making a drink containing ¼ soda and  ¾ vodka.

Your first date:
You’re not into “models” or men who think they are models, but the dating scene has been dry af lately and you figured, why not? He surprises you by asking you on a date to The MET. When you get there, he’s wearing jeans with ironed plaid patches and you want to vomit. You obviously have to proceed and when you find out he’s a member of the museum, you think “maybe I’m judging this guy too much.” Wrong. You start asking questions to get to know him, like where he grew up and what he does for work in the city. He answers all your questions and reciprocates none.

The date ends within 45 minutes after he asks if you want to come back to his place. It’s 1 pm on a Sunday and he’s clearly the worst person ever. You’re also on the Upper East Side. He lives in the East Village. You already know the answer is no, but envisioning the awkward train ride makes it a hard no. After ordering an Uber home, he asks if he can join because it’ll drop him “closer to the train”. You say sure, even though you shouldn’t, and he tries to make a move on you in the car. Your body is protruding hate for this man and he cannot catch a hint to save his life. You eventually part ways and you immediately shower to wash the cringe off your body. 0/10. 

The relationship:
There is no relationship. Period. 

Why it didn’t work out:
It didn’t work out because you have values and morals. You love yourself too much to ever interact with a human like that again. 

3. The Virgin

Who is he:
Late 20’s/early 30’s quiet guy with a sweet soul. He’s an architect, loves his dog named Jack, and looks adorable in a button-down shirt. 

Where you could find him on the weekends:
Reading a book in his West Village apartment or wandering around the Guggenheim. 

Your first date:
You meet at a cafe on the Upper West Side that he recommended. It’s a cute place, the perfect spot for a first date. You sit down and immediately pick up that he is a shy guy, but he’s talkative when you ask the right questions and he is curious about you too. He’s soft-spoken and you can tell that you’re scaring him with your slightly overwhelming, talkative personality. You leave the cafe and you walk around the neighborhood together. You eventually part ways with a hug. 8/10.

The relationship:
You continue to see each other for two months, around once a week. You’re always getting dinners or drinks or going to a movie, which is fine. However, you slowly notice that it’s YOU who always makes the first move. You keep hoping he will put his hand on your leg or put his arm around you but nothing, even when he’s slightly tipsy. You contemplate with your friends if he is a virgin. It doesn’t seem too far out of the loop. He eventually sends you a text asking where you see the relationship going, and you tell him nowhere because there isn’t enough proven affection after two months. You both agree and are on the same page. You wish each other well and gracefully go your separate ways. 

Why it didn’t work out:
Although you loved to talk to him and he was incredibly intellectual, your personalities did not align and neither did your love languages. And that’s okay. You learn that you enjoy people with a humble attitude like his, which you add to your mental list of attributes you desire in someone. 

Disclaimer: I want to make it clear that I don’t actually think that this guy was a virgin, but even if he was, there is nothing wrong with that. You are allowed to make your own decisions regarding your body and what you feel comfortable with doing. Always live your best life at your own pace. 

4. The Ghost

Who is he:
Mid/late 20’s guy who has the perfect clean-cut beard, an intense passion for snowboarding, and an extensive collection of whiskey on his IKEA bar cart in his apartment.  

Where you could find him on the weekends:
Bars hopping with his “buds” in the West Village or at home watching The Office.

Your first date:
This is the first date you’ve gone on in an extremely long time. You’ve never been more nervous, so what do you do? You have your two friends tag along. And by tag along, I mean that they sit at the table across from you to watch you on your date (you realize how insane this is looking back at it). Anyways, you meet up with your date and are at the bar for hours.

You talk about basic first date things, and you can’t help but notice how cute he looks in his glasses. You’re there for so long that your friends eventually bounce (not until accidentally taking a picture of you two with the flash on) and you can tell the bartender wants you to leave so you can free up some seats for other people. The date eventually ends and he calls you a cab to head home. He’s kind, you like him and enjoyed your time together. 9/10.

The relationship:
You date for a few months and are really into him. He’s constantly checking in on you, taking you out to dinner, and making you breakfast when you sleepover. He even invites you on a trip to Boston for an upcoming weekend. Everything is perfect! Then one day, he goes silent. You don’t hear from him for days, weeks, and eventually an entire month. You accept the fact that he’s a low life douche, and start to move on. Then one day, he texts you. He says that his mom has been sick and he went back home (across the country) to care for her. He tells you he’s moving back there. You’re compassionate with the fact that his mom is sick but you let him know you don’t want to hear from him ever again.

After you do some sleuthing online, you find out that his mom is not sick and that he moved back to the west coast to be with his girlfriend of 3 years. Yup. You read that right. Two years later, he texts you and asks you to grab drinks because he’s coming to the city. You answer with a “who is this?” because you genuinely didn’t know and he tells you. You plan a time to meet up the next day at your favorite bar you used to go to together.  The next day rolls around, and he lets you know he is on his way to the bar. You reply with “same!” and immediately block his number, obviously never speaking to him again. Not. Sorry. 

Why it didn’t work out:
It didn’t work because he was an expert manipulator and HAD A GIRLFRIEND the entire time. If that isn’t a big enough reason as to why it didn’t work out, then I don’t know what is.  

5. The “He’s Perfect!…JK”

Who is he:
Mid 20’s guy who works at a travel startup, lives with 2 roommates in Brooklyn, and always has a black coffee in his hand. 

Where you could find him on the weekends:
Hanging out at a bar with live music or smoking on his rooftop.

Your first date:
You meet up on a Friday night at a bar that is way too packed for its own good. Together, you wander the street together for a little bit, trying to find another place and come across a nearly empty bar. You sit, start getting to know each other, and even take a tequila shot with him to commemorate the date. The bartender asks if it’s your first time meeting because it’s super obvious. You end up spending hours together, hanging out in the back of a few old dive bars. It’s probably one of the best dates of your life. 10/10. 

The relationship:
You hang out two or three more times. He’s hilarious, and your energy bounces off each other seamlessly. But you realize that you may be trying too hard to impress him, and it seems that he is doing the same. After a few weeks, you mutually ghost each other, with no reason or explanation of doing so. And not one ounce of you cares. You realize you may need therapy. He still views your IG stories to this day. 

Why it didn’t work out:
It didn’t work because even though you had a great time together, and you really thought he was perfect in the beginning, the universe did not want you to be with someone you had to force a fake version of yourself. And the universe always knows best. 

6. The Finance Bro

Who is he:
You already know who I’m talking about. A late 20 something dude that wears vests every day, works as an investment banker and probably has a CitiBike membership.

Where you could find him on the weekends:
Either working or blacked out in an Uber on the way to his ex’s apartment. No in-between. 

Your first date:
After rescheduling 3 times due to his busy schedule, you meet at a bar in FiDi on a weekday after work. He’s finishing up a phone call when you sit down and he tells you that you look nice. Things are going well until you tell him what you do for work, and he says “that’s cute” and continues to talk about his job. Throughout the date, he can’t stop talking about his obsession with Thai food and his upcoming trip to Spain. He wipes his nose on his sleeve twice. You eventually call it a night, and he tells you he’s going to meet up with more friends at another bar. It’s Tuesday. But despite him being a slight douche, he had a good sense of humor which is hard to come by. 6/10. 

The relationship:
You give him a few more chances because although he wasn’t the best, he also wasn’t the worst. Who knows? Maybe he’ll grow on you. You hang out two or three more times, just to have something to do. You realize he likes alcohol a little too much and he is completely proud of his obnoxious ora. He thinks he is a 10, when in fact, his cockiness makes him a 4. And he always has a clearly visible booger in his nose. 

Why it didn’t work out:
Do I really need to explain this one? He’s turned out to be the worst. You like a confident guy! But when they are full of themselves and require a drink of humble juice, you walk. And to top it all off, he wears a vest. Need I say more?

7. The Guy Who Can’t Move On

Who is he:
Early/mid 30’s dude who has an expensive taste for red wine, loves to go camping upstate, and just got out of a 7-year relationship. 

Where you could find him on the weekends:
Ordering takeout from his favorite sushi restaurant or at a small get together with his closest friends or family. 

Your first date:
You meet at a bar in Murray Hill, which is not your go-to area for a date, but it works. He’s waiting outside for you and greets you with a warm hug. You go inside, have a few drinks and you can tell he has an extremely friendly, welcoming vibe. His personality levels perfectly with yours and before you know it, you’ve gone to a few more bars and it’s 1 am. He’s very upfront about the fact that he recently got out of a long term relationship, which doesn’t bother you. You end the night and go your separate ways with plans to meet up in Central Park the next day. 8/10.

The relationship:
You date for a while. And for a while, I mean a few months. Months of seeing each other once or twice a week, having sleepovers, going on dinner dates, the whole 9 yards. You can tell he’s into you, even though you’re not confident that you feel the same. Primarily because he talks about his ex a little too much for your comfort. But you try not to let it bother you because you know that he is only trying to heal. You eventually start to realize that he’s actually a good guy and you may be developing feelings for him. Then, the night you want to ask him where he thinks the relationship will go, BAM!!!!! He tells you he’s getting back with his ex-girlfriend. You’re disappointed, but not surprised in the least. It was nice while it lasted. 

Why it didn’t work out:
He was a good guy, but clearly he was using you to try and move on from his feelings of pain and regret from his previous relationship. You don’t blame him. You know what they say, the best way to get over someone is to get under someone else! However, that clearly did not work for him. It’s for the best that he and his ex are back together because you are not okay with being a bandaid for someone’s broken heart. 

8. The Part-Time Ghost

Who is he:
Mid 20’s HUNK of a man. He has the perfect beard/mustache combo, wears skinny jeans that are a little too tight for him, and is an expert on every type of craft beer.

Where you could find him on the weekends:
Playing Jenga with his giant group of friends or playing darts at his favorite bar down the street from his apartment.

Your first date:
After attempting to make plans for a few weeks, you meet at a cool bar in the East Village. He’s way taller than you realized (which is always a plus) and he has a cool vibe to him. You both order the spiciest drink on the menu, so you automatically know you’re going to get along. You talk about everything under the sun, and you can tell you both enjoy analyzing each other’s minds. He seems moderately promising, although he is definitely a slight oversharer. The date ends after a few more hours and a few more drinks. 9/10. 

The relationship:
You continue to see each other for about two months. You’re constantly having a blast, it’s like hanging out with your best friend. But there’s one thing you can’t shake. His communication style. He answers your texts days, sometimes weeks, after you send it. You’re bummed about this because he seems great but you know that communication is of the utmost importance to you. You are not in a relationship and this is not something you care to bring up after knowing someone only for a few months. So essentially, you accept the fact that you’re taking the “L” (No, not the train). Your last exchange ever was asking him when he’s free next, him telling you he’ll “let you know” and then mutually ghosting each other, never speaking again. 

Why it didn’t work out:
Someone can showcase many ways as to why they’re a great person. They can make you laugh endlessly, and you can do fun activities together without feeling a ton of pressure. But if there’s a clear habit of inconsistent communication, you acknowledge this is something that will never change, especially from a grown man. You still think about him from time to time and wonder if something would have worked out between you two. But then you remember that once he answered your text two weeks later and he talked about his gingivitis on the first date. You get over that feeling fairly quickly.

Moral of the Story

And that, friends, is my take Dating in NYC: The Men You’ll Meet. Before you go, I’ll leave you with this.

You’re going to date many types of people in New York City. During your time dating, you must always maintain yourself as a priority.  Use every meeting as a learning experience to help you narrow down what you like and do not like. And always remember, it is okay to be selfish in every decision you make throughout your life.

Okay, I’m done for now. But please share with me your experiences here! I want to hear EVERYTHING! And lookout for more articles like this in the future.