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Dating in Your 40's As A Man: Dating Tips From A Dating Coach

How to Date At 40 (or even 50!) Dating in your 40's as a man might be easier than you thought.

I just began working with a new client named James. Something amazing happened to him on a hotel-rooftop bar in Manhattan. He did something he thought was impossible.

But in dating, as in life, sometimes you can surprise yourself.

James came to me wanting to know how to date at 40 or 50. (In his case, over 50!) Dating at any age can be challenging for men, but when you’re north of 40, you start dealing with doubts relating to your age.

If you’re anything like James, you might think, “Amazing women want young, cool guys—not some older, middle-age man.”

You might think you’re past your “sell-by” date.

You might think it will feel “creepy” or “awkward” to flirt with a woman who’s more than a few years younger than you.

Here’s the problem with filling your head with those doubts: You create a self-fulfilling prophecy that kills your dating life and your self-esteem.

What I mean is, if you feel you’re too old to attract women of any age, then your actions and behaviors will mirror your fears and doubts. So you probably won’t make an effort to learn how to date at 40, and so you’ll barely date at all.

And if you DO walk up to that younger, cute woman you see at the bar, at the coffee-shop, at the grocery store, she won’t feel your confidence. She’ll feel your fear and doubt, and she’ll reject you.

But she’s not rejecting YOU, or your age, or your “pickup” line. She’s merely rejecting the energy that those negative beliefs create.

dating in your 40's as a manYet when you adopt a new belief about what you offer as the awesome man you are, then your mood, your energy, your charisma—it all goes through the roof.

And women LOVE a confident man (of ANY age).

In the area of women and dating, your beliefs are your destiny.

To go deeper, let’s return to my client James.

As an NYC dating coach, I get to take guys out on the town as their personal wing man. James is newly single and wanted to learn how to date as an older guy.

James was married for 20+ years, and then endured a brutal divorce that dragged on for years. Custody battles. Splitting up property. Heart-ache. Not to mention the impact on James’ children. It was wrenching.

Plus, his ex-wife has moved on to another man, while James has been alone, feeling low and lonely.

Sure, he’s a successful guy, but he hasn’t dated in decades. So he’s felt limited in terms of the kinds of women he can date.

So we took a good, hard look at his beliefs about what women find attractive. We also looked at James’ beliefs about himself, and what makes him a great catch.

James was so caught up in his fears and doubts that he lost sight of some important facts:

He’s a great dad, the father of three wonderful daughters.

He has a successful business that he built with his own two hands.

He’s funny, fun-loving, and warm. (“I’m snuggly,” he says.)

He likes and respects women and wants to make genuine, mutual connections.

I asked James to shift his focus, from all those doubts to all of these great qualities he has to offer.

As we sat talking in his hotel lobby, ready to hit the town together, I told him, “Tonight, let’s focus on what you OFFER, not what you lack.”

Because when you shift your focus from your doubts (“I’m too old/short/poor/ugly”) to your qualities (“I’m awesome/smart/funny/successful”), and then you take action, then AMAZING things unfold.

And that’s what happened one recent Saturday night at an upscale rooftop lounge in Manhattan.

Now, it had been decades since James went out to chat up women, so it was a win for him just to be out talking, flirting, enjoying people. And just by using some techniques and moves I gave him, he became more and more “in the zone” and started getting girls’ phone numbers.

And then it happened.

latina - how to date at 40A gorgeous, shapely Latina in a red dress walked by. James approached. He was charming and disarming. She looked at him, her almond eyes grew huge, and she smiled.

The look of instant, mutual attraction.

Sofia is 30—more than 20 years younger than James—and she was INSTANTLY into him. They were inseparable the rest of the night—flirting, holding hands, kissing. They melted into each other. Their sexual chemistry was palpable. They looked like a couple. They just… fit. They traded numbers and made a date for later in the week.

That’s right—a 50-plus, divorced dad who hasn’t dated since the Clinton Administration ignited CRAZY chemistry with a smart, sexy, 30-year-old woman who could have picked any guy in the bar. But she liked him.

And all James had to do was let go of the FALSE stories about his lack of attractiveness, and tell a new story about all the awesome things he has to offer.

It’s beautiful to see a man shed fear and doubt so that he can connect with an amazing woman in an authentic way.

Here’s the truth about how to date at 40 (and over):

When you build the right beliefs, take action, and let chemistry happen, age is pretty much irrelevant.

And this goes for dating at any age.

James is 50+. Sofia is 30. Didn’t matter to her. All she knew is that she had chemistry with a cool man of value. His age is beside the point.

So he now has a wonderful new woman in his life because he adopted a powerful belief, and then aligned his actions with his belief.

Plus, James now knows FOR A FACT that he can attract women in their 30s, 40s or 50s. He can cultivate a dating life that’s about abundance, choice and genuine connections with wonderful women (rather than limitations and settling.)

And when he falls for that truly fantastic woman, and she falls for him, he can settle down and create a great relationship. ALL by being 100% authentic and himself, NOT pretending to be something he’s not.

New beliefs lead to new actions. New actions lead to AMAZING results. the hero inside - dateless to dating

OK, and a good dating coach helps, too. 🙂

GREAT dating at any age is 100% learnable. Dating in your 40's as a man (or even 50 and up) can be a wonderful thing. The first step? The right beliefs!

So, if you’re ready to learn about dating in your 40's as a man, or how to date at 50 or any other age, here’s what you can do right now.


We’ll chat for 45-60 minutes, and you’ll get the advice and guidance you need to take the shortest possible path to the dating life of your dreams—whether want a great girlfriend to share your life with, or an abundance of dating options.

An important heads up. PLEASE only book a call if you’re ALL three of these things: 1) Truly committed to taking action 2) Decisive 3) Someone who likes and respects women. If you aren’t those three things, then you and I are not a good fit.

But if that does sound like you, and if you’re ready attract amazing women as your most authentic, confident self, then CLICK HERE TO BOOK A FREE CALL.

And we’ll talk soon.

For advice on dating after divorce click here. For recommendations on dating books for men, click here.

Connell Barrett is an acclaimed NYC dating coach for men. He helps men around the world authentically connect with amazing women. Connell has appeared on shows like Access Hollywood and The Today Show as well as in publications like O Magazine, Maxim and Cosmopolitan. Book a call with Connell here.

Click here to book your free call with dating coach Connell Barrett
Connell Barrett Dating coach for men

I'm dating coach Connell Barrett. I help men build confidence and connect with women by being authentic!

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NYC Dating Coach Connell Barrett

106 W 32nd St, New York, NY 10001

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