Dating in New York City: Tips for Introverted Men

When it comes to dating in New York City, the only sure thing is that it will be interesting. Whether pleasant-interesting or unpleasant-interesting, that reveals itself as you go along.

Whether you bonded with her over your love of the Waystation’s Doctor Who theme and felt particularly bold and comfortable with her that night, or whether your conversation fell flat (or worse)…

There is always a lot to learn about yourself while dating in New York City.

There are also a lot of opinions about the dating scene in New York City in general.


Foggy NYC Street View - Dating in New York CitySome hate it.

One look at this article, and you’d be tempted to run for the hills into a quaint land far far away. While this post is particularly negative and cynical, it does point out three real challenges about dating in New York City:

1. For one thing, there are so many options.

This can lead to one or both people being non-committal after one date (or several), even when things are “going really well” and they enjoy each other.

Reason being, with so many options constantly walking right by you, it’s easy to slip into an eternal waiting for “something better” to come along.


2. Another challenge is meeting women in person.

You may want to step away from technology for awhile and connect with women in person.

That can be hard to do in NYC, as a lot of people are on Tinder or Bumble and may not be as open to the natural ebb and flow of a conversation with an intriguing new person.

That said, it is far from impossible.

You just need to know how to actually do it, which we’ll cover further down in this article.


3. It can be hard to get to the second date. 

With so many single people around, actually moving from Date 1 to Date 2 can be more of a challenge than you may have thought.

While the “non-committal” mode can start early, it doesn’t have to be that way.

I’ll show you a few ways to make sure things move to a second date with the women you meet who are genuine fits from both sides.

Dating in New York City is full of more than just challenges. For some people, it’s one gigantic adventure.


Sunny NYC Day View - Dating in New York CitySome love it.

I loved reading this write-up of dating in New York City.

Here’s what the author says is amazing about dating in New York City:

1. You can have super high standards and still meet amazing people.

She writes…

“In all honesty, I started to love dating when I started trusting my gut and stopped going out with people who didn’t text me back, or who wouldn’t make solid plans, or who clearly (or not-so-clearly) didn’t share my values.” 

Yes! Amen to standards and trusting your intuition.


2. There are adventures around every corner. 

You could go to a different bar every night for 100 nights and still not go to them all. (You’d in fact only be going to 1/15th of them, even after all that!)

Not only is there a variety in bars and all sorts of happy hour venues; there is also a variety of single women you’ll meet and date in New York City.

With 8 million people, it’s the most diverse and interesting group in the country.


3. Dating in New York City is a particularly colorful experience, compared to anywhere else. 

There’s also a really funny article on dating in New York City from a woman’s perspective.

It’s the whole enchilada of humor, complete with GIFs and reasons to laugh out loud (as I did when I read the end of #2).


Streets of NYC - Dating in New York CityWhat dating successfully in NYC looks like

Successful NYC dating comes down to two things:


1. Feeling awesome

To truly enjoy dating in New York City, you must feel awesome in your own skin.

At Introverted Alpha where we work with accomplished introverted men, we like to use the phrase “Benevolent Badass.”

The original Latin roots of the word “benevolent” are why I love the word so much:

“Bene” means “good” and “voleo” means “power”, so benevolent translates to “using your power for good”.

What I love about that is the assumed power. You have power, and you’re using that power you already have (your willpower, your sense of agency, your own two legs!) for the good of those around you.

I love the word “badass” because it communicates a strong sense of self. 

You know what you want, and you go after it which is so attractive.

To find your own attractive benevolent badass vibe, check out this free ebook.

Feeling like a benevolent badass makes dating in New York City a whole lot of fun.

Reason being, for each person and situation where you’re a benevolent badass is different and makes you feel creative and resourceful in the moment! You can discover much more about this here.


Woman at Coffee Shop- Dating in New York City2. Dating great women

Dating women who are quality is a big part of a happy NYC dating life.

They’re warm, intelligent, expressive… or deep and mysterious!

Whatever is your cup of tea, you can find it while dating in New York City. 

(Hey, that rhymes!)

Even if you’ve happened into a date with someone who isn’t quite what you were looking for, then…

(A) Yay for standards about your personal preferences!
(B) The night is not wasted because you can still learn something.

In fact, the more dates you have that are subpar experiences, the more opportunities you have to learn and refine your approach for next time.

For example, could you tell in her Tinder profile that she was a bit of a messy drinker?

Or when you met her at that party near Central Park, did you notice (if you remember back) that she was preoccupied and not present with you?

The more you reflect on your experiences and take your findings into account for next time, the better women you’ll start meeting in the dating pool of New York City.


NYC Night View - Dating in New York CityHow to make dating in New York City effective and fun

There are three main steps to make dating in New York City a really great experience for yourself, whether you tend to hang out in Manhattan, Brooklyn, Long Island, or all of the above.


1. Benevolent Badass Pre-work

No one comes out of the womb feeling like a Benevolent Badass through and through, knowing everything about what he wants and what he brings to the table!

That takes time and focused attention.

There are three main steps to this process:


1. Understand why you are already sexually attractive. 

If you’re used to seeing the most gregarious man at a party get all the attention, you might wonder what on earth you have that is sexually appealing to women.

Well, friend, chances are you have a lot.

Check out this in-depth article on how to internalize the fact that introverted men are attractive and this ebook with an exercise (page 8!) on finding your own charm.


2. Get clear and unapologetic about what you want. 

Once you are feeling good about what you’re ALREADY bringing to the table, you can start considering what type of person you’d like to take on an amazing date.

What kind of values does she have? What kind of disposition?

Don’t be afraid to get specific. You’re looking for a match here, not a perfect woman.

So you don’t need to be a perfect man, but you do need to be on the level of what you’re looking for.

To win a catch while dating in New York City, you must be a catch!


3. Become the catch you seek. 

If you’re worried that the kind of woman you want is “out of your league,” then make some inspiring life changes to catch up to her before you meet!

If she’s fit and healthy and you’ve been slacking a bit, get your behind back to the gym.

Not only will you feel great from the workout; you will be putting your mind to something and taking TANGIBLE ACTION to make it happen.

(I know this is easier said than done, which is why we have our 1:1 coaching program.)


Grand Central Station Rush Hour - Dating in New York City2. Meeting Women

There are two ways to meet women in NYC:

Through online dating apps, or the old-fashioned way: in real life.

Simple enough, right?

We wrote mega posts on each of these!


1. Read our online dating success guide for introverted men.

It goes over everything from dating site profile photos to the best dating apps this year to messages and more.


2. Read our guide for introverted men on approaching women in person.

It will tell you what to say in different venues (get our full venues list), how to make conversation once you’ve said hello, and more.


3. Read our five places for introverted men to meet women

You can try out one of our recommendations in that article, give a speed dating event a whirl, or let your friends know you’re single to see if you can meet a friend of a friend who’s already vouched for.


3. Getting Dates

Once you’re reading her well and seeing that things are going swimmingly, it’s time to get her number and schedule the date!

Rule #1 to actually having a scheduled date happen:


1. Don’t flake. 

Simple as that. If you (a) want the date to happen and (b) want to look like a badass, be a man of your word.


2. Have a high bar for the women not flaking either.

It’s POSSIBLE. There are so many smart, with-the-program New Yorkers. Surely you can find a date a week who will meet you when and where she says she will!


Two Espressos on Table - Dating in New York CityFirst Date Venues and Conversation

Best First Date Venues in NYC

The best venues for you to take a date to are (a) fun or expressive of your personalities and/or (b) a simple cup of coffee or a drink.

A great hybrid of these two is an (a) interesting (b) coffee/drink!

There are so many coffee shops and bars that are eclectic, classy, sophisticated, amusing, or whatever is the vibe you’re looking for!


Two Conversations: Touch and Words

If you are thinking the only conversation you’re having is with your words, you are mistaken.

For a woman, the MOST important conversation is the one your body is having with her body, as two human beings.

You don’t have to be touching the whole time for her to get a feel for how it is to be near you.

Even being in proximity to you will give her an idea of how it would feel to be even closer.

Still, if you work in some friendly touch with her, you’re giving her a chance to feel into how you are and let you know if she’s into you. You can discover much more about this here.


Sunrise NYC - Dating in New York City

Dating tips for NYC

1. Embrace the way it is. 

Yes, it’s fast-paced. That means you meet more women in a shorter span of time, supercharging your NYC single life.

Yes, there’s competition, especially when dating in New York City. You can use that as inspiration to be the best version of yourself.

You can’t please everyone, and awesomely you don’t need to.

Rather, you simply must be the best version of yourself if you’re seeking to attract a genuinely awesome woman who is the same.

EMBRACE IT. That will put you miles ahead of all the men sitting around complaining about it!


2. Avoid the Complainer Face

The “Complainer Face” is a sad event that happens when a grown man feels like a victim of his own circumstances. IT IS NOT PRETTY.

In fact, the “Complainer Face” is not a sexy look for anyone: man, woman, or child. Case in point:

via GIPHY 

Instead, use the tips in this article to help you take control of your dating life in New York City to feel awesome in your own skin, meet great women, and go on adventures!



How do you date successfully in New York City as an introverted man?

By becoming a better man every day.

As you explore and develop along the way while dating in New York City, good things happen.

You become a stronger and more “you” man in the process on all fronts (because dating affects other facets of life).

You will also be learning more and better skills of how to best relate to women, and your success will follow suit.

*Note: All of the above doesn’t just apply to straight men. If you are among the gay men in New York City, awesome! You can apply this dating advice to yourself, simply switching out “woman” for “man”. In fact, some of our most successful clients have been gay men who have done just that and have gone on to meet and date awesome men and feel like badasses in the process. 

To see how we can help you make swift progress in your dating life in NYC and beyond, check out our dating coaching program page.

And if you’ve not downloaded our free ebook, “Why PUA Doesn’t Work for Introverts & What Works Instead,” get your copy right here. It will help you solve the problem of trying to be someone you’re not and find your own distinctive charm in a world of mostly extroverts.

Picture of Sarah from IA
Sarah from IA
Sarah is founder and CEO of Introverted Alpha; the top dating coaching company for introverted men; featured by Forbes, Business Insider, Cosmo, and more. Pick up your free copy of Introverted Alpha's 22-page ebook in the box below.

Attracting An Amazing Girlfriend Starts with Finding Your Own Vibe.

Introverted Alpha Ebook

In this powerful free 22-page ebook, “Why PUA Doesn’t Work for Introverts And What Works Instead,” you will uncover… 

–> 3-step exercise to find what makes you uniquely attractive

–> Why the “pickup artist” approach will never work for introverts and what works instead

–> How to attract women naturally being your best self

"I love how personalized and caring you guys are at Introverted Alpha! It's so wholesome and refreshing." - I.L.

"I especially like how you’re a strong alternative to short-term, shallow PUA tactics." - K.K.

Recent Articles

Leaving Already?

Before You Go...

Schedule a call with us to improve your dating life immediately.

Couple In Love - IA Academy - Introverted Alpha

Attracting An Amazing Girlfriend Starts With Finding Your Own Vibe.

In this powerful free 22-page ebook, "Why PUA Doesn't Work for Introverts And What Works Instead," you will uncover...


--> A 3-step exercise to find what makes you uniquely attractive
--> Why the “pickup artist” approach will never work for introverts and what works instead

--> How to attract women naturally being your best self

We respect your privacy; we do not sell or share your email address.

Introverted Alpha Ebook

Yes, please send my ebooks!

You can send them to...

Yes, please send my ebook!

You can send it to...

Scroll to Top