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Dating Tips for Shy Guys

Dating coach Connell Barrett answers your questions on how introverted men can succeed with women, a smooth way to ask a girl out, and the secret to approaching with total confidence. Here are dating tips for shy guys.

Dating Tips for Shy Guys

Connell, I’m a pretty introverted, and that’s always held me back with women. I don’t like going to bars, clubs, etc. I prefer quiet places, like bookstores and museums. Do you have any dating tips for shy guys like me? 

—Gerald, 27, Boston

Gerald, you might think that being introverted is a dating drawback, but it’s actually a strength. (I say this as a card-carrying introvert myself.) When it comes to offering dating tips for shy guys, I always think of my client (and friend) Andy. 

Andy is naturally introverted, but that doesn’t stop him from having a great love life. In fact, it helps him. 

Sure, making that initial approach can be intimidating and draining for the introverted guy. But once a “quiet” guy is one-on-one with a woman, he’s in his strength zone. He’s self-aware, smart, and a great listener. Women love guys like that. 

Andy and I were at a party once, and this loud, brash guy was hitting on all the girls, talking AT women, not with them. (And he was striking out.) Meanwhile, I turn and see Andy on a couch cuddling up with a gorgeous brunette he had just met, both of them snuggled up under a blanket. 

As a dating coach who’s worked with thousands of single men, I’ve found that women are actually MORE attracted to introverts than they are to extroverted guys. Shy, introverted guys have several dating advantages over the dudes with the lampshades on their heads. Such as…

  • Introverts cultivate deeper connections. Why? Because we’re good at one-on-one interactions, such as dates. 
  • The “quiet ones” are great listeners. Women like to be truly heard, and listening comes naturally to the introverted brain. We talk WITH women, not at them.  
  • Introverts are self-aware and reflective. That kind of depth and intelligence is attractive. (It doesn’t hurt that we can seem a bit mysterious, which girls find intriguing.)
  • We’re self-contained, not needy. Extroverts need attention, but we don’t. 
  • Introverted men prefer “big” talk over small talk, and who doesn’t love stimulating conversation on a date?

My best dating tip for shy guys: Make a shift and understand that you’re every bit as attractive as those outgoing extroverts—maybe even MORE attractive. 


When I’m messaging on an app, it feels cheesy to say, “Hey, what’s your number?” Sometimes I never ask, and then she goes quiet. What’s a smooth way to ask a girl for a girl’s digits? 

—Kevin, 37, Kansas City 

Here’s how to make the move with charm. After you’ve swapped a few fun, flirty messages, text her this: “So, how are you enjoying our conversation, on a scale of 1 to (999)-999-9999?” Her digits will soon be headed your way. 


I see cute girls at my gym who I would love to approach, but I never do. Just yesterday this yoga cutie was standing near the drinking fountain, and I didn’t say a word. I was kicking myself all day! But I don’t want to seem creepy. How do you make yourself approach when you’re scared of rejection?

—Mark, 33, Tampa

Mark, here’s a quick story, about my client, Jared, 37, a U.S. Navy captain. 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’d been 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.  

“I can’t believe THAT is what I’ve been so afraid of all these years,” Jared said. “That didn’t hurt at all.”

When you realize there’s nothing to fear, you become free to approach with confidence. 

Currently, you see rejection as something to fear, but you should actually see it as something to embrace. It’s good for you. It’s part of the process. 

My dating philosophy comes down to one word: authenticity. I teach men to be Radically Authentic, drawing their confidence and awesomeness from within. And when you learn to do that, you realize that no one can reject you except for YOU. 

I always thought rejection in dating was a bad thing—something to avoid. But it’s actually something to embrace. 

Now, I don’t mean that you should TRY to get rejected. Just that rejection is nothing to fear. It's not a personal judgment on you. It’s part of the process. It thickens your hide. 

Mark, think about the woman at your gym. She can’t REALLY reject you because she doesn’t even know you. Now, if your wife of seven years sat you down and said, “You’ve never given me an orgasm, and I’m leaving you for David Beckham,” OK, THAT’s rejection. But a random girl at your gym can’t truly reject you. 

You shouldn’t fear rejection any more than a Major League slugger should fear striking out. Mickey Mantle struck out three times as often as he hit home-runs. Imagine if in his rookie season, The Mick struck out a few times and then said, “I retire!” Or imagine that he grew so timid that he stopped swinging for the fences and ONLY bunted.  

This is what lots of guys do in dating. They either retire or they bunt. They basically give up (never approach, never take risks), or they play it safe and settle.  

So, the next time you see that girl at your gym, remember—she can’t really reject you. But even if she said, “I’m not interested,” you’d realize that the sky did not fall, that you are still here—corporeal, alive. And that’s when you’ll be free from the fear of rejection, and can approach ALL of those girls you’d love to meet. 

Embrace rejection. It thickens your skin. It means you're doing it (dating) right. Only by exposing yourselves to it will you realize, “Hey, that wasn’t so bad.” 

And then you can swing for the fences. 

Connell Barrett is a dating coach who provides dating tips for shy guys. He helps men learn how to get out of the friend zone and find the right woman. Connell has been published in magazines such as O Magazine, Cosmopolitan and Maxim. He's also appeared on talk shows including Access Hollywood and The Today Show.

You May Also Like:

Dating As An Introverted Man Podcast Episode 

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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