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Post Grad Advice: Dating in New York City

Everyone is always saying New York City is a dating city - well, I wouldn't know because I've been dating my college boyfriend for the last 3 (almost 4) years (shoutout to DMWEISS) so I solicited the help of my 3 close (and single) friends to get their take on dating in the big apple. Its funny, its raw, its really honest. Enjoy!


Meet Luke

Date Outfit inspiration - Wear it from work straight to the bars

Age: 23

Interested in: Women

Moved to NYC: 1 year 6 months ago

How do you normally meet people you are attracted to?

"I’ve met women on dating apps, but they haven’t worked out very well besides for just a hook up. I definitely think people can meet on dating apps, but I meet most women at the bars, through friends, etc.

Manhattan is the easiest to meet women. Queens has less options, but it's just a numbers game."

Which dating apps do you use?


  • Way more options of Women because they don't have to send the first message


  • Less de-stigmatized because women aren't afraid to admit they are on Bumble,

  • More professional and better quality (but not as active on the app)

When you get a women's number, do you use a texting strategy?

"Yes - immediately when I get a woman’s number, in person, I will text her my first and last name. This strategy works for me because:

1. We can both look each other up on social media. Usually you meet the woman, they’re a little drunk, a lot going on, but then they'll go look me up and think '‘oh yeah I remember him, he’s good looking’ and thendecide if their interested. There are so many times when you question yourself in the morning with ‘Was that woman hot? Or was I just drunk?’ And being able to go on social media helps from both ends

2. Since I sent a text message of my name to them, I am up on their most recent texts, and they are on mine, so it’s easier to remember rather than searching through my address book

After a few days, I’ll go and text the woman. If it’s done too soon, it looks needy and you’ll end up scaring them off.

If I get a woman’s number Thursday or Friday, I will text them on Monday. Never text someone on Sunday because people are trying to relax, chill and not trying to start texting a guy they just met. When the texting conversation starts, I try to text like I talk. I don’t like to play games while texting, unless the she's consistently waiting 20 minutes to respond…then I’ll match her and do the same. I’m not a big texter and like conversation better in person, so I’ll suggest after a few texts back and forth to grab drinks together.

Advice...don’t ever overthink what you want to say because it’ll come off weird and corny"

What types of dates do you go on in NYC?

"On your first date with someone, I never do weekend date nights because I know I am better than whatever she has planned on a Wednesday night andI know I can beat that. Friday and Saturday….she’s got plans, something fun to do and I’m not going to try to compete with that.

The dates I go on depends on if person wants to drink or not. Some people don’t want to drink during the week, which is fine, but think of something creative to do for us.

Note: I always kiss a woman on the first date. Unless its apparent that it won’t happen - which means it was a bad date. I usually try to bring it up when the conversation takes a pause and I know it’s going well by saying “you know, I’ve been wondering if I’m going to get a kiss tonight” and either they shut down the idea or laugh. That way at the end of the night, they know I’ll go for it."

What are your turn on's / turn off's while on a date?

Turn On's - Authentic (if it doesn't work out, then it as natural), talking about your job, family, your goals

Turn Off's - Fake (everyone can see through it), being on your phone during the date, when a woman says they were 'super wasted' and only want to talk about partying

When you meet a person, do you usually go on one date or multiple before you decide if you are still attracted to them?

"There have been a good number of first dates, and a few women I’ve seen a few times, but nothing serious. At our age in Manhattan, people aren’t looking for a serious relationship right now.

For me, I’m looking for someone to build chemistry with, but not settle down. I think it’s important to date people because that’s how you figure out what you’re looking for. You can always take something from a relationship, even though they weren’t the one and it didn’t work out.

If I met the right woman, then I would try to make it work and settle down."

Who pays the bill?

"Me. It’s just the way I like to do it. I don’t want to come off as cheap, and don’t mind. It’s part of taking the woman out since I am the one inviting the woman out on the date."


Meet Kristen

Date Outfit Inspiration - Edge with Class

Age: 25

Interested in: Men

Moved to NYC: 1 year 6 months ago

How do you normally meet people you are attracted to?

"Usually I meet people at the bar or dating apps. I feel like every date I’ve been on for an app has not been as successful. Also, not everyone looks like their profile picture."

Which dating apps do you use?

The League

  • Can view which school the person went to ( an easy conversation starter)

  • Shows your interest

  • "I think that helps as a buffer because if someone I am looking at is a personal trainer, I won’t have much in common with them as someone who is in consulting. It’s nice to have something right away to know you can talk about in common"

  • Less matches per day (less intense / overwhelming)


  • Enjoys using it (but wishes women did not  have to make the first move. More pressure to be funny or interesting to start conversation)

When you get a guy's number, do you use a texting strategy?

"My motto is: the less chemistry over text, the better the date will be - hopefully because: 

1. You haven’t crossed over all those good date conversations

2. You have so much more to talk about in person

Some people are just bad texters. I don't text very well and I often forget to respond to someone if I read it and then put my phone down - which is far too often. When I do text, I try to be funny, or witty and when words fail - GIFs. Or ask interesting and totally weird "Ice Breakers" Example: 'Buckets for hands or or buckets for feet?' or 'cheetos for fingers or carrots for toes?' ... this sounds way more pathetic on a social platform like this but I've genuinely gotten a ton of entertainment from hypotheticals."

What types of dates do you go on in NYC?

"Always drinking. Late drinks. Depending on how good the date is, you’ll either get drunk because it’s fun, or drunk because it’s not fun because you don’t want to be there. If you want to leave, you can use the excuse of going to go hang out with your friends or if you don’t want to leave, you can continue to hang out.

There is never dinner or any wildly creative dates - which I appreciate. Anything over the top is just too much pressure. I went on one coffee date and walked along the water in Brooklyn near the Williamsburg bridge, and then we went to dinner because I it was going well. It felt so romantically forced, but I still went along because, well you know "you never know". We sat down, still having an interesting/fun conversation and I was like "ooh everything looks so good I can't decide, let's split two things" and he just looked me straight faced and serious: "why don't you just choose one and you eat that and I'll choose one and I'll eat that". And I'll be damned if I'll ever speak to that freak again."

What are your turn on's / turn off's while on a date?

Turn on’s - Passionate foodie, funny, interesting, intelligent

Turn off’s - People who are closed minded, weird mannerisms, always on the phone, someone that talks about themselves the entire date

When you meet a person, do you usually go on one date or multiple before you decide if you are still attracted to them?

"I'm really picky, so usually I find something about the guy that doesn’t make me want to see them again, or vice versa. Guys definitely have more options than women in NYC because we out-number them. I think guys get a mentality of not wanting or needing to settle down because you can find some other model to date. LOL. but really.

When I first moved to the city, I wanted to date non-stop just to date. Now that I’ve done it, I'm only going on dates with guys that I'm really interested in. I am asking myself if I'm feeling a connection, was the conversation good, is this someone I would want to see again, etc."

Who pays the bill?

"Half the time the guy pays, but the other half we split the bill. I do like if guys pay because it’s a nice gesture. Usually, I insist on splitting because I feel awkward having the guy pay an expensive New York City bar tab."


Meet Sam

Outfit Inspiration - Keep it casual

Age: 24

Interested in: Men

Moved to NYC: 1 year 5 months ago

How do you normally meet people you are attracted to?

"I go out with friends, I don’t go out with the mindset of seeing someone. If I see someone that I'm interested in and feeling good, then I'll go over and start a conversation. Also, I use apps."

Which dating apps do you use?

"Oh, 100%. I like Bumble, Hinge, Chappy. I’ll admit that I visit Grind every now and then.


  • Best success rate


  • Most information about a person


  • Can put in whether you’re looking to date seriously or just meet up for whatever. 

  • Provides info on where they live, links to social media, etc. 

Also, I like seeing their social media accounts, like Instagram, to help get a better sense of the person. I’ll even look at their following ratio - if they follow a ton of people, but only have 3 followers, that’s a little weird."

When you get a guy's number, do you use a texting strategy?

"I usually see how the other person texts. If they are into the conversation and I’m into them, there is no algorithm going on in my head. If they are just sucking at texting, I am going to play some games. If the conversation is awkward and I don’t think I am going to last any longer, then I will talk about literally anything and that will be it for me. If you can’t hold a conversation with me, even though we’ve talked for a week or two, then that is not good compatibility.

What really bothers me is after two responses into the conversation messaging, a guy will ask to go get drinks. I’m thinking to myself NO, I don’t know you, I don’t trust you, I don’t really get who you are yet. I like to talk for awhile, understand their humor, follow them on Instagram. I’d rather FaceTime or talk on the phone before meeting in person. People are crazy and weird….you could talk to them, meet up in person and they just end up being so creepy."

What types of dates do you go on in NYC?

"Drink or dinner date. Get a drink during the week. Usually a quieter environment on the weekdays and it makes it easier to talk."

What are your turn on's / turn off's while on a date?

Turn On's - Good personality, sense of humor, fantastic smile, someone who thinks I'm funny

Turn Off's - Bad personality (I’m sassy but hate when a guy is too sassy. One time this guy had his eyes at the ceiling the whole date because he kept rolling his eyes at me. Didn’t really get what his end game was."

When you meet a person, do you usually go on one date or multiple before you decide if you are still attracted to them?

"Prefer to text them a couple times, and then it doesn't really go past that. It usually ends because I become unattracted to them, or they become an ass*hole."

Who pays the bill?

"I usually try to pay the bill because it makes me look good."

Shout out to Luke, Kristen and Sam for all your help, honesty and laughs to make this blog post possible!

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