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First Date Tips For Men

Dating coach Connell Barrett answers your questions on first date tips for men, how to dial up romantic connection, and when you should NOT go on a second date.

FIRST DATE TIPS FOR MEN

My first dates all seem to go nowhere. We just have boring conversation, and she’s checking her phone before she’s done with the first drink. How can I make my first dates go better?

—Billy, 24, London, England

When it comes to first-date tips for men, here’s the secret to success in a single word: authenticity. Be real, be you. 

And I’ll bet you’re making a mistake that lots of guys commit on first dates: You carefully monitor your every word, trying to be “attractive” and not make a mistake. That stifles your most charismatic, awesome self, and leads to boring dates for her and for you. 

Forget about all that. Instead, keep it real, yo. We’re all searching for truth and realness, so get in the habit of sharing scary but honest feelings with women—as long as it’s not vulgar or negative, of course. This emotional nakedness is mesmerizing to others, and by going first, you free your date to do the same. 

Such phrases often start out like this: 

  • “You know what I like about you…”
  • “Here’s what scares me the most…”
  • “I want to share something with you, but I’m not sure if I should…”

To be extra brave, say one (or all) of the above phrases to your next date without knowing how you’ll finish the thought! As long as you’re being authentic and present, your brain will figure out the “right words,” and your date will know that they’re real.

There’s NOTHING boring about an authentic man putting his real feelings on the line. 

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“YOU’RE LOOKING AT ME LIKE I’M DESSERT”

First Date Tips for Men. Dating Chemistry.

I’m so tired of women seeing me as just a nice guy, rather than a potential romantic partner. On dates, I see other couples all over each other, but my dates never want to jump my bones. 

—Seth, 39, Austin, Texas

Seth, I totally get it. It can sting to see other people hooking up, and to be on a date with a cool, gorgeous woman who’s two feet away from you—but she may as well be two miles away, in terms of her attraction. 

But you CAN be a nice guy and learn how to have those sexy, fun, connected dates that lead to unforgettable nights. 

Once, during a trip to L.A., I met Valerie, an ambitious women’s-fashion expert. For our first date, we had drinks at a patio bar in Venice Beach, near my hotel. We seemed very different on paper. Her: a Black woman who went from an inner-city upbringing to managing a Santa Monica boutique—with plans to open her own place. Me: a privileged white guy from the Midwestern burbs. But our romantic chemistry was off the charts. 

We both felt the sexual tension rising as we teased, talked, and laughed. At one point, my wolfish eye contact made her say, “You’re looking at me like I’m dessert.” As we walked back to my hotel, she was unbuttoning her top before I had my key in the door. 

One of the tools I used that night is simple: I moved my eyes in a “7” pattern, which helped me unlock the mutual attraction that Valerie and I had for each other. 

So, to dial up the sexual tension on dates, move your eyes in a “7” pattern—that is, from her right eye to her left eye and down to her lips. This will amplify your attraction for her, which enhances something called “emotional state transference.” Emotions are contagious—what you feel, a woman will feel. If you let yourself get lost in her baby blues, you can transfer the desire that you feel onto her. 

For more tips, see "5 Flirty First-Date Questions That Spark Attraction."

WHEN NOT TO HAVE A SECOND DATE

Should I go on a second date even if the first date was just so-so?

—Michael, 44, Albany, N.Y.

Consider a second date with these 3 questions.

If you find the woman attractive and “your type,” consider giving them a second date—even if the first one was just so-so. Just as we have off days, we also have off dates. The two of you could be a great romantic fit, but if one of you was nervous, tired or just not on your game, it can throw chemistry off.

Now, if your date was mediocre because the other person is simply not what you’re looking for, then you should bail. But if they mostly match your blueprint for a partner, pull the trigger on date no. 2. There’s little to lose and lots to gain. 

Here are three questions to ask yourself before deciding on a second date. 

  • Was there at least a little chemistry? 
  • Did the conversation flow well?
  • Did she focus on you—and you on her—rather than just making it about yourselves.   

If you said yes to all three, a second date is a no-brainer. Two yeses? Lean toward having date no. 2. But if you said yes only once or not at all, cut your losses and move on. 

Life is too short to settle for disappointing dates. 


Connell Barrett is a dating coach from NYC and he has been called one of the best dating coaches in the world. He specializes in actionable advice for men to help them find their dream woman. His advice has been featured in talk shows such as Access Hollywood and the Today Show. Furthermore, his advice has been featured in Maxim, Cosmopolitan, O Magazine, and more. His new dating book for men is being released in Spring 2021. Ask Connell a question below.

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First Date Advice for Guys

NYC Dating Coach Connell Barrett

106 W 32nd St, New York, NY 10001

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