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How To Win A Girl Over On A First Date Without Being Friend Zoned

Dating coach Connell Barrett answers your questions on the secret to flirting, effective approaching, and how to win a girl over on a first date without being friend zoned.

How To Win A Girl Over On The First Date Without Being Friend Zoned

I need your help to get out of the dreaded friend zone. I rarely go out on dates, and when I do it seems I always hear some version of, “You’re a nice guy, but I’m not feeling that chemistry.” It’s starting to take a toll on my confidence. Thoughts, coach? 

—Jesse, 34, Boston

The dreaded friend zone has tortured more people than the Rack. And I totally know where you’re coming from. I didn’t merely live in the friend zone. I owned vast tracts of real estate there… and paid property tax.

I had dozens of first dates that basically went nowhere, and it can really sting to receive that next day, “I’m not feeling it,” text message, especially if you felt that the date went reasonably well, with good conversation.

So, let’s handle this right here and now. Here’s how to finally free yourself from the friend zone on dates, of course, but also when you’re messaging women on the apps or over text, as well as when you’re on the phone or doing a video date.

The secret is blessedly simple. Tell her—in a true, authentic, real way—that a specific trait about her is very sexy.

And even if it scares you, I want you to use that exact word: sexy.

Friends don’t call each other sexy, but men and women who are romantically interested DO.

Let the feeling arise from a true place inside of you. A little voice may tell you, “Damn, she’s so smart/funny/cool. That’s so sexy.”

Tell her! Yes, even if you feel a little fear.

Telling a woman that she’s sexy sends her a loud, clear, confident message that lets her know, “I’m not here to be ‘just friends.’ I want something more than that.”

A real, radically authentic man must summon the cojones to show his romantic intent, in a charming, empathetic way. This lets your date know that you’re interested, and also that you have the courage to be vulnerable, and to take that risk.

And women both want to feel sexy, and they want to date confident, risk-taking men.

So, for her, it’s a win-win.

If you’re thinking, “Won’t I sound creepy?” No, not if it’s a TRAIT that you find super sexy about her, rather than just focusing on her looks or a part of her body.

Don’t misunderstand: Any woman would want to be seen as physically desirable to her type of guy. But complimenting her curves or her lips or looks is what all the other guys do.

But you? You will be that rare, insightful, courageous man who sees her inner beauty and sexiness… and women love that kind of man more than I love karaoke. (You should hear my “Total Eclipse of the Heart.”)  

So, on your very next date, take a moment and notice her inner sexiness—her wicked wit or presence or silliness—and say something like, “Wow, I really like [her inner quality]. It’s really sexy.”

Tell women you meet for dates that they’re sexy—and MEAN it, saying it from an authentic place—and that’s how to win a girl over on a first date.  

THE ART OF THE "DIRECT APPROACH"

Man and woman dating - how to win a girl over on a first date

I do approach women, but it doesn’t go anywhere. I say, “Hey, do you have the time?” or maybe I try to crack a joke or say something funny, but I never seem to create that spark. How do I approach with more success, to get numbers and dates?

—Troy, 29, Philadelphia 

Try being more direct in your “opener”—the first words you say when approaching a woman.

When you open a conversation with a woman, it’s not as much what you say as HOW you say it. You need full commitment, and clarity that tells her why you’re talking to her.

Your opener does NOT have to be clever or fancy—just good enough to get her to respond. I’ve begun conversations with openers as simple as these:

  • 
Hi
  • You have great style. 

  • How’s your night going? 

  • I feel awesome today, and I had to share it with you. 

  • What book are you reading? 

  • Is this the coolest club around here? 

  • Whoa, this line is long.

Being clever or funny is a nice bonus, but it’s just not necessary. Simple and clear is best.

And one of the best ways to be clear is to make your opener direct. What’s that look like? Quick story.

My client Oscar was having a drink with friends at a Miami lounge when he saw Anastasia, a tall, intelligent pharmaceutical rep. He approached her, they liked each other, and later left the bar together.

The next day, his impressed (and envious) buddy asked Oscar what he said to Anastasia. What amazing opener did he use on her? Oscar explained, “I just said, ‘Damn, who are you?’ My vibe was, ‘I’m into you. You into me? Cool. Let’s get outta here.’ I’m a man, and she’s a woman. Why would it NOT be like that?”

Oscar used what’s called a direct opener – meaning that his romantic intentions were clear from the get-go.

“Going direct” on your IRL opener means that your words and/or vibe convey clear romantic interest from the get-go. Here are examples of direct openers.

  • Hi, I saw you and had to meet you. 

  • You’re absolutely adorable. 

  • You’re gorgeous. Who are you? 

  • I’m here to flirt with you. 

  • You’re sexy and I had to say hi. 


The upside to being direct: there’s no chance of the friend zone. She’ll know whether or not she’s attracted to you, and why you’re talking to her. Lots of women love direct men, so it can ignite instant interest. And it can feel freeing to shed weighty expectations and just be real with women from the start, rather than trying to find something witty or clever.

The downside to being direct: it’s a polarizing technique, so plenty of women will reject you right away. If she’s not available or just not in the mood, she’ll hold up a big, fat stop sign. Either sparks will fly or she will—as she walks away.

Quick Tip: Directness is not a license to be vulgar. If you go direct, don’t make it about her body, and don’t say anything about sexual acts. “You’re sexy” is about as blunt as you want to be. 


Yes, it takes a shot of courage (if not Jim Beam) to deliver a direct approach. But when it lands, and a woman shows you that clear, immediate interest, it’s worth it.

YOUR PLACE OR MINE?

Man and woman at bar

When I meet a woman out at night, at the bars, what’s the best way to get her back to my place?

—Martin, 41, Hartford, Conn.  

I have a crazy take on this: Ask her!

Be transparent. Never hide your intentions or try to manipulate her. It’s dishonest and ineffective.

Once, while leaving a club with a girl I had just met, I took a pickup coach’s advice and gave her intentionally vague details about where we were going. “I’m taking you someplace you will love,” I said as we got in a cab, implying that we were heading to another bar.

When we pulled up in front of my apartment building, she was disappointed. “You know, you could have just invited me over,” she said. “I would have said yes.” I felt sketchy.

When you want to invite a woman you just met to come back to your place, do two things. First, invite her to another spot—grab another drink, go get pizza—so that you can both get more comfortable with each other.

Next, as things are winding down there, be sincere. Say, “I’m having so much fun with you, and I don’t want the night to end. Want to come over and [fun, PG-rated thing you can do]?”

It’s not about the “thing,” of course. It’s about the two of you getting more time together. Learning how to win a girl over on a first date isn’t hard. It just takes an honest, direct, and committed approach.

Want some tips on dating tips for shy guys or flirty questions to ask a girl? Read Connell's column here and subscribe so you never miss an update!

 

Want to be coached by Connell? Order the book Dating Sucks But You Don't, and learn how to approach women and get the girl here. It comes with incredible bonuses like live group coaching!

 

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 print in Maxim, O Magazine, and Cosmopolitan. Ask Connell a question below!

 

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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!

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NYC Dating Coach Connell Barrett

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