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Approach a Woman with Confidence

How do you approach a woman with confidence? Dating coach Connell Barrett answers your questions on the secret to destroying approach anxiety, how to be “cool” on dates, and the mindsets that assure romantic success.


I really want to go out and approach women in parks, coffee shops, and maybe in bars, but every time I try, I can’t do it—I have so much approach anxiety. Any advice?

—Mark, 39, Denver

Mark, your question reminds me a lot of my client Jared, a 37-year-old captain at West Point. So, here’s a quick story.

As the two of us walked into Madison Square Park on a spring day to meet women, the beads of sweat on his forehead revealed his nervousness. “I’ve never approached girls before,” he said, with a lump in his throat.

He feared (cue: scary music) rejection. But he quickly got two phone numbers, one from a cute pre-med student out walking her dog, the second from a Brazilian exchange student lounging on a blanket. Two for two!

Next, Jared approached a woman on a bench, her nose in a book. He came back a few minutes later with a huge grin on his face. I assumed he’d grabbed a third number, but it was the opposite.

He was rejected. And I’d never seen him happier.

“It was fantastic,” he said. “She said, ‘I just want to read my book. Bye.’ So I bounced.”

“Yet you survived,” I said, poking his shoulder. You’re still here.”

As good as getting two phone numbers felt, his aha! moment was realizing that with the right mindset, rejection is no biggie. 

That’s what I’ve been so afraid of all these years?” Jared said. “That didn’t hurt at all. There is nothing to fear.” And when there’s nothing to fear, you become free to approach a woman with confidence.


date night with wine - approach a woman

Connell, I’ve been trying to use cool lines on dates and when I approach a woman, and be all mysterious, but it seems to fall flat. Help!

—Mickey, 29, Austin

Mickey, some guys think you attract women by being chicly unengaged and mysterious. You know, “cool.” But women don’t want cool. They want real.

I’m shamelessly uncool. A total dork. I love bad movies and dad jokes. I spontaneously sing show tunes in daily life (with jazz hands). I take classes in coin magic. (Coin magic!) Hardly the hallmarks of a ladies’ man.

But when you’re uncool without apology, you’re free to be you—which is super cool. And women who like your brand of uncool will see a twin spirit, which heightens connection. “You’re so weird,” my girlfriend said on our second date. “As weird as me.” I tried being old-school cool, but the proverbial biker jacket just doesn’t fit me. The real me is a nice, nerdy redhead from the Midwest.

If you’re uncool, own it. And that makes you really cool.

On a final note, make sure you—hey, what’s that in your ear? Why, it’s a silver dollar!


man and woman having drinks- approach a woman

I read your book, “Dating Sucks but You Don’t,” and I love what you said about how success with women is all about your mindset and what you believe—not just what you say. Can you talk more about that?

—Russell, 45, Boston

Happy to, my man. Here are the 5 bedrock beliefs that virtually assure you dating success. If you do NOTHING ELSE besides live by these mantras, you will almost certainly transform your romantic results.


When I was a junior in college, I wrote a weekly humor column for the campus newspaper. It was a popular feature, but I was painfully insecure about my writing. One day, a fan letter from a journalism professor appeared in my mailbox. “You may not know how good you are,” the professor said of my writing, before telling me about the promising career that awaited me. That letter, that sentence, was the booster shot of confidence that I badly needed. 

You may not know how good YOU are. If you wonder whether or not you’re good enough to date wonderful women and get a great girlfriend, you absolutely are—in ways big and small.

Buy into this. Because when you believe it, everything shifts.


Accept the truth that a great partner will be in your life. It’s a done deal—it’s just a matter of when, not if. It is about focusing on what you want, rather than what you fear. Anxiety and inaction come from playing a horror movie in your mind. So play a different flick, one that shows you a compelling outcome.

I’m not talking about a ruthless fixation on success. Don’t go all “Whiplash” on yourself. Simply soak in the certitude that an incredible love life awaits. It will happen.

This is not woo-woo, “law of attraction” mumbo jumbo. It’s practical psychology. When you commit to a compelling goal, your subconscious says, “Let’s do this!” And to keep you honest, your brain does a dickishly-cool thing by making you stressed out if your actions don’t align with your goal. To avoid this pain, you act in accordance with your desires, and your mind eliminates many of the shitty thoughts and behaviors that hold you back.

Also, this kind of fierce focus helps you perform at a higher level. This is what great athletes do. In his prime, on his way to winning fifteen majors, Tiger Woods would stand on the tee and picture the blade of grass on which his ball would land some 350 yards away. By focusing on where he was going, he worried less about sand traps and lakes. This relaxed him, facilitating his best play. 

See and feel your outcome—the confidence, the romantic connection—and your inner self will find a way to make it happen. 


Love handles or washboard abs? Being dead broke or Richie Rich wealthy? Unlucky in love or honeymooning in Hawaii? Our progress in any area, or lack thereof, comes from our rituals, the actions we take consistently. Committing to daily action will propel you toward the romantic fulfillment you desire.

You can visualize and meditate and get your kumbayas out all day long, but if you don’t take consistent, ritualized action, your chance of failure is high. Vision boards and goals scribbled on paper are all dead wood without the discipline to act.

But don’t think you need to improve in leaps and bounds right away. Yes, you can have big breakthroughs, but don’t underestimate the power of steady, incremental improvement. “The difference a tiny improvement can make over time is astounding,” James Clear writes in his book Atomic Habits, adding, “[I]f you can get 1 percent better each day for one year, you’ll end up thirty-seven times better by the time you’re done.”

Good looks are WAY overrated. Consistent action is WAY underrated.

Ritualize consistent action for romantic results.


With apologies to FDR, the only thing we have to fear is ignoring fear itself. Fear can be a friend, a powerful force to harness, a call to action.

If you’re afraid to approach a woman or go for the first-date kiss, that’s fear telling you exactly what you should do. Your love life is like a boat, and fear is the ocean wind. You can use those gusts to reach your destination, or do nothing and be lost at sea. As Tony Robbins said at a seminar, “You can’t control the wind, but you can control the sails.”

If you do one scary but necessary thing every day, you’ll see incredible results faster than you ever thought possible.


Thomas Edison failed to invent the lightbulb hundreds of times. Abraham Lincoln failed to win almost every election he entered, until 1860. J. K. Rowling failed to sell the first Harry Potter manuscript twenty-two times.

So-called “failure” is just part of the path to achievement. So don’t be afraid to fail big and to fail often. Then fail again and again and again…

Until you succeed.

Connell Barrett is a NYC dating coach for men. He's helped men all over the world find the woman of their dreams with actionable advice. His work has been featured on Access Hollywood and the Today Show. In addition, you can find him in Maxim, O Magazine, and Cosmopolitan. Read his book Dating Sucks But You Don't.

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Connell Barrett Dating coach for men

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

dating sucks but you don't #1 Amazon bestseller

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NYC Dating Coach Connell Barrett

106 W 32nd St, New York, NY 10001

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