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:

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.

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 how to get a girlfriend 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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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.

APPROACH A WOMAN WITH CONFIDENCE

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.

HOW TO BE “COOL” ON DATES

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!

TO ASSURE DATING SUCCESS, TAKE 5!

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.

1: YOU ARE ENOUGH

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.

2: WHEN YOU FOCUS ON AN AMAZING OUTCOME, YOUR MIND MAKES IT HAPPEN   

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. 

3: RITUALS EQUAL RESULTS 

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.

4: FEAR IS YOUR FRIEND, NOT YOUR FOE

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.

5: FAILURE IS THE SECRET TO RESULTS

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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"Dating Sucks But You Don’t"

Dating coach Connell Barrett gives exclusive tips on his book, Dating Sucks But You Don't. In addition, he answers your questions on the right way to approach, how to defeat self-doubt, and online-dating openers that work.

Dating Sucks But You Don't

So psyched! I’ve just launched my new book, DATING SUCKS BUT YOU DON’T: The Modern Guy’s Guide to Total Confidence, Romantic Connection, and Finding the Perfect Partner.

Here are three common dating problems guys have—and three practical fixes taken directly from my book!

How do you approach women in a way that’s charming, rather than creepy?

-Leif, 27, Ohio

When I started learning how to attract women, I was at a trendy hotel lounge in New York City one night. My wingman challenged me to approach a table where a cute brunette and her blonde friend sat with a muscular guy.

At that point, I was still nervous about talking to women, let alone dealing with a potentially pissed-off boyfriend. And this guy was huge, like a bottle of Muscle Milk made corporeal. But I summoned the courage, walked over, grabbed an empty chair, and offered a warm hello.

The brunette’s eyes widened and she leaned forward. “Oh my god! You came right up and talked to us. Do you know what you are?” (I thought, Umm, a creep who’s about to get his butt kicked?) “You’re normal!” She tilted her head toward a fellow sitting a couple tables away. “That guy’s been staring at us all night, and it’s creeping us out!”

Oh, and the hulking dude I was worried about? Super friendly.

I traded numbers with the brunette, who was as charming and friendly as she was pretty.

Most men don’t approach women, often from a fear of appearing creepy. But it’s much creepier to want to approach yet do nothing and stare instead.

Confidence does not come free. You have to pay for it. How? With courage.

Courage is the currency that buys you confidence.

If you want the confidence to approach and attract beautiful women, you have to start doing it first, and the confidence will come… in time.

Your move? Follow the three-second rule.

 

When you’re in a social environment and you see a woman you’d love to meet, approach her immediately. Begin walking toward her within three seconds of spotting her.

The longer you wait, the harder it gets.

The longer you wait, the heavier the wait.

Use the three-second rule. Three, two, one… go!

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The Secret to Dating Confidence

I lack confidence with certain women. I feel they’re out of my league. How do I get to the point of feeling attractive and “enough” for them?

-Bill, 33, Knoxville

the secret to confidence. "Dating Sucks But You Don't"

If you feel “not enough” for certain women, it’s because your Lower Self is running your love life.

As my decade studying dating successes has revealed, you, me, everyone—we all have dual selves. A Higher Self and a Lower Self.

Your Higher Self is the hero of your life. In any arena that brings you joy, fulfillment, and results, your Higher Self is in charge. He’s confident, focused, and totally authentic.

He’s you operating at full potential. The job you love, the biceps you’ve sculpted, the great kid you’re raising—it’s the superhero inside of you running the show.

But every superhero has an arch-villain, a mustache-twirling bad guy. And that’s your Lower Self.

This is the fearful, doubtful part of you who’s been botching up your love life. It’s the voice that whispers, “Don’t approach her—she’s out of your league.”

The pain and frustrations you’ve felt—from settling to the friend zone to feeling unworthy of quality women—that’s all the fault of your Lower Self.

Higher Self = You at Your Best

Lower Self = You at Your Worst

There’s great power in understanding your enemy. On the first day of their training, I have my clients give their Lower Selves a name—a nickname to make them cringe. Fred, an attorney in his late thirties, came to me because he would feel a lot of stress and fear when he wanted to say hello to an attractive stranger—what’s called “approach anxiety.” His hands would shake at the thought of walking up to a woman and saying hi, so he named his Lower Self “Frightened Freddie.”

Me? My Lower Self is “Connie,” a grade-school nickname that I hated and that now reminds me of the pain my Lower Self caused.

Next, I have my clients recall a specific moment of awesomeness—a time when they felt fulfilled, confident, and present. These mental snapshots can really be anything, from crossing the finish line at a marathon, to playing electric guitar in a band, or laughing with close friends or family.

Then they give that guy a name, because he’s their Higher Self—and he’s capable of doing incredible things. “Frightened Freddie” became “Frederick the Great,” a guy who could soon successfully approach women almost anywhere. My Higher Self’s name? It’s so stupid that it’s brilliant: I went from “Connie” to “Connell Fuckin’ Barrett,” a bold man of action. (You can call me CFB for short.)

Your Lower Self contains all the pain and doubt and approach anxiety that contributed to your sucky dating life. But your Higher Self has bottomless confidence and can get lots of dates, and in time connect with one incredible woman.

To be clear, your Higher Self is not a persona or a mask. Nor is he you after a couple stiff whiskeys. He’s the inner you buried beneath layers of doubts and fears—that priceless, gleaming diamond encased by worthless igneous rock.

Dating Sucks But You Don’t is about how to drill down to that Higher Self and put him in charge of your dating life. It’s time to hand your Lower Self a cigarette and blindfold and let your Higher Self run your love life.

Your Higher Self is in EVERY woman’s league.

Open All Night: Dating App Openers that Work!

I get matches with women on Tinder and Hinge, but they almost never reply to my openers. Help!

-Charles, 36, Atlanta

opening lines for Tinder

Here are three fun, effective ways to write your openers.

 

1: The Compliment + Question

Look at her bio and see what strikes you as quirky, interesting, or cool—say, her style, her love for hiking, her fondness for Steve Carell movies. Tell her what impressed you, and ask her a question that she would enjoy answering. A great way to approach a question is to makes her an expert. (We all love being experts.) Use her name, and limit yourself to two emojis.

“Katie… I see you’re a Steve Carell fan. Awesome. OK, lemme ask you. Do you think he’s better in comedies or dramas?”

You’re making her an expert in a topic she’s interested in, while also showing that you read her bio. She’s likely to reply.

2: Compliment + Tease

You pay a sincere, specific compliment—but instead of asking a question, you tease her about something, such as her favorite TV shows or a silly accessory she’s wearing in a shot. (Never tease about anything she would likely take offense to, such as her weight, other bodily features, or anything that’s too personal.) Let’s say her bio mentions traveling in Europe, and in one shot she’s wearing a bold, colorful hat.

“Katie, wow! You’ve back-packed all over Europe? I’m impressed. But I’m curious… did the fashion police in Italy arrest you for that giant hat?”

A compliment paired with a tease can be very engaging, enticing her to spar with you.

3: The Knock-Knock Joke

This comes courtesy of “Great Love Debate” podcast host and fellow dating expert Brian Howie. Your opener is simply: “Knock-knock…”

That’s all! Believe it or not, this type of opener has a crazy-high response rate. She’ll likely reply with “Who’s there?”, and you proceed with the knock-knock joke of your choice. It sets the perfect playful tone. (I don’t know about you, but I wouldn’t want to date a woman who didn’t reply to a knock-knock joke.)

I prefer personalized openers, but here are five one-size-fits-all ice-breakers that also work well. (Make sure to include the woman’s name so it feels more specific to her.)

 

No. 1 Amazon bestseller Dating Sucks but You Don’t is available wherever books are sold. To order it, or to learn how it will transform your confidence and love life, go to DatingTransformation.com/book

Want some tips on what to say when asking a girl out or where to go on a first date? 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 such as how to get out of the friend zone. 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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Escape The Friend Zone

Dating coach Connell Barrett answers your questions on how to escape the friend zone on first dates, becoming more charismatic, and dating tips for a post-pandemic world.

Escape The Friend Zone

Do I have to go for the kiss on first date? I feel stuck. On one hand, I know I need to make a move or else I’ll have to escape the friend zone. On the other, I don’t want to make a woman feel uncomfortable with a forced kiss. What do I do?

—Eric, 27, Oklahoma City

Here’s a quick story, Eric, about what NOT to do when you want to escape the friend zone. It happened to me over a decade ago, when I was going on tons of dates to try to “crack the code” of connecting with women.

Stephanie and I were walking to the subway station after a first date.

“Kiss her,” I thought as we walked to the subway station. “It’s now or never.”

When Stephanie and I stopped at a crosswalk near the end of our first date, I went for it. But she had been checking her phone, so when she looked up, my incoming lips must have seemed like a sneak attack. She recoiled, and I caught the corner of her pursed mouth.

“God, I’m so sorry,” I said, feeling clumsy and creepy.

“Umm, it’s okay,” she said, vanishing down the steps to catch her train. “G’nite.”

There was no second date.

Looking back years later, I now realize my rookie mistake. I call it the Lunge.

It happens near the end of a date. Sensing that he’s been playing it too safe, a guy feels the pressure to make a move to keep from getting friend-zoned. But he doesn’t want his date to feel uncomfortable, especially in the #MeToo era.

Finally, feeling the need to do SOMETHING, he goes for the kiss, like a quarterback heaving a desperation, fourth-down pass. Surprised, the woman either pulls back or endures an awkward lip-lock.

So you definitely don’t want to sit on your hands for a three-hour date, and then lunge at her. She won’t appreciate the courage. It will seem try-hard and uncomfortable, for both of you. And she’ll probably not want to see you again.

Instead, take the “stair-step” approach. Take small, flirtatious steps—ALWAYS noticing how she’s responding so that you can adjust accordingly. (Empathy is just plain sexy.)

If you’re on a date, greet her with a warm hug. Move on to playful taps on her arm or shoulder. Hold eye contact. Open up and connect emotionally. Notice if she’s laughing, enjoying you, and initiating touch herself. Hold her hand. Is she holding yours back and leaning in? If yes, she’s ready to kiss. Go. Now.

Save your lunges for the gym.

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Yawn Maintenance

Maybe I’m just a boring guy, but women on my dates yawn a lot. Any suggestions on how I can keep their interest and just be more interesting and charismatic?

—Dominick, 29, Los Angeles

escape the friend zone. become more charismatic

Your dates are yawning? Easy fix. Instead of cocktails, take her out for a couple glasses of 5-Hour Energy.

Better yet, here’s a shortcut to charisma: Get good at storytelling. You want her dropping her jaw in awe, not in boredom.

We’re ALL hardwired to love stories. A good, personal story from your life makes you more charismatic, holds her interest, and invites her to share her own stories—which can amplify connection. Here are three storytelling tips.

1: Use a three-part structure: setting, conflict, resolution

Here’s a story from my teenage years that I’ve told on many dates: “I was in study hall in high school [setting] before a geometry test. I wasn’t ready, and if I failed I’d end up in summer school [conflict]. So I shut my textbook, went to the nurse, and pretended to have back spasms. When my parents came, instead of taking me home, they drove me to the hospital for an MRI and X-rays. I had to wear a hospital gown and everything. And the doctor diagnosed me with scoliosis—for fake back spasms! [resolution]. My poor mom started to cry, not realizing the whole thing was a scam.”

2: Details!

Specifics bring a story to life, making it more vivid. Your high-school English teacher was right when she scribbled on your term paper: “Show, don’t tell!”

In my story above, it’s the specifics (the textbook, the hospital gown, my mom’s tears) that makes it so vivid—and keeps the audience’s rapt attention.

3: Tell vulnerable tales

Avoid stories meant to make you look “cool.” It’s much cooler to laugh about an embarrassing moment from your past. For example, the time you struck out and lost the game, not the time you hit the home run to win the game. Vulnerability is powerful and attractive. My “fake scoliosis” story works in part because it makes me look like a schmuck. The story impresses not by trying to make me seem cool, but by my willingness to look like an idiot—and laugh about it.   

But don’t overthink it. Some of the best stories are just weird, funny incidents. Travel adventures work well. My client Craig loves telling his dates about the time his friends snuck him into Canada by rolling him inside of a carpet and putting him in the back of an SUV.

Getting Back in the Game

I haven’t dated in over a year because of the pandemic. For that matter, I’ve barely looked a person in the eye IRL. I’m probably gonna have to learn how to be with people all over again. Any help?

—James, 37, Fort Wayne, Indiana

post pandemic dating

If you feel anxious about “getting back out there” for IRL dating, remember—everyone will be nervous! In addition to dating butterflies, we’ll also have post-pandemic nerves. Remembering that we’re all in this together should relax you.

Here are some pointers to help smooth your journey from pandemic dating to a more normal world (bring it on!).

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 such as what to say on Tinder and how to get a girlfriend. 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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14 Deep Questions To Ask a Girl

Dating coach Connell Barrett provides deep questions to ask a girl, the secret to motivation, and the easy way to flirt with charm.

Deep Questions To Ask a Girl

I know I need to keep things light when getting to know a woman, but I also love having deeper, stimulating conversations. Is it OK to “go deep” and talk about real stuff? What are some deep questions to ask a girl?

—Carter, 40, Auburn Hills, Mich.

Early on in a recent relationship—two or three dates in—Brianna and I were sitting on her couch playing Scrabble when she asked me if I’d ever cheated on any of my exes.

“Yes,” I said. “More than I care to admit.”

Her reaction? Understandable shock at my infidelity, but she also felt something bordering on excitement. I was being so bracingly candid with her, and that part she liked.

I went on to tell her why I had been unfaithful, and how I had learned from it—and, of course, had mended my ways. (I used to be a mind-bogglingly self-interested person.) The talk brought us closer together.

Now, I’m not saying that on date no. 2, you should admit all your past sins. I just want to underscore the power of “going there” and having a deep conversation.

Yes, Carter, the overall vibe of your interactions in the courtship phase of dating should be light and fun. But you can—and should—burrow below the surface.

Real talk can create real connection. The right questions can help you both become more vulnerable and emotionally naked.

Here are 14 deep questions to ask a girl. (Heads up! Always be prepared to answer any question that you ask. And “deep” does NOT mean “depressing.” (Keep things positive!)

1: “What was the best day of your life?”

This summons good vibes, gets you both swapping stories, and makes you share a sense of gratitude. (I LOVE talking about my dad’s surprise 85th birthday party, which I planned with my three sisters… and which my ailing mom was able to witness not long before she passed. Best. Day. Ever.)

2: Who is your hero?

Whether it’s her dad, a former college professor, or Harriet Tubman, her answer to this question will give you a deep insight into who she admires as well as who she is at her authentic core.

3: What’s the most courageous thing you’ve ever done?

This question lets you take turns talking about being the hero in the story of your life.

4: If you could go back in time and give your younger self some advice, what would it be?

A fun time-travel thought experiment that lets you admit regret and share life lessons.

5: What’s your biggest flaw?

Don’t give the bullshit, job-interview answer here. (“I care too much.”) Keep it real, yo! It takes confidence to admit flaws, and women love confident men.

6. What do you love most about your job/career?

This question lets you both talk about work in a positive, emotionally evocative way, rather than boringly asking her, “What do you do?” And you can follow up with, “Why do you love that so much?” This helps her dig deeper.

7. What’s your hidden talent?

Can she do cartwheels? Rock the karaoke mic? Recite all the state capitals? This question allows her to show off a bit while also revealing a secret—and sharing small secrets builds trust on first dates.

8. What’s your dream travel destination?

Hey, everyone likes talking travel. It’s aspirational, and the two of you might find out you’re both just dying to see Machu Picchu, or run with the bulls in Pamplona.

9: Who would you want to play you in the movie of your life?

This question caters to your date’s ego—and the actor that she chooses will clue you in on how she sees herself.

10: Who did you see for your first concert? 

Music is a great first-date topic. Prepare to be impressed when she mentions Beyoncé, or playfully tease her when she admits that it was Nickelback.

11: What’s a favorite memory from childhood? 

A first date once told a great story from grade-school, about the time she got dressed up as a clown for Halloween and went to school… on the wrong day! All the other kids were dressed normally, while she sat there in her red wig and clown makeup. Sharing stories from childhood offers your date a chance to be vulnerable or tell funny stories. Also, teeing your date up to tell a story lets them shine, and take center stage.

12: What do you love to do for fun?

We all love to talk about our passions and hobbies, so this question is likely to kick-start a stimulating conversation. To take it up a notch, add some cheeky confidence by saying this, with a sly grin: “What do you love to do for fun—besides go on first dates with charming, attractive men like me?”

13: Who was your first kiss?

Everyone remembers their first kiss. This question takes things in a romantic direction, but also keeps the vibe innocent. But you can spice things up by asking…

14: What’s the craziest place you’ve hooked up?

If things are going well and you’re both opening up, feel free to ask this riskier, PG-13 question, which can help spark a sexy vibe. Just be ready to answer your own question!

Now that you have a list of fun, deep questions to ask a girl. Go try them out!

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What's My Motivation?

I know I should be out trying to date, but I just don’t feel motivated. And it’s taking a toll. I’ve gained about 20 pounds during lockdown, my social skills have all but vanished, and I’m lonely. I’d love to find a wonderful girlfriend, but I can’t get excited about dating. Can you give me some motivation?

—Gabriel, Portland, Ore.

couple outdoors - deep questions to ask a girl

At the end of “The Wizard Of Oz,” the Scarecrow, Lion and Tin-Man all learn that what they wanted—brains, courage, heart—was within them all along.

Motivation works the same way. No one can give it to you. You have to summon it from inside.

Here’s a great way to do that. Give yourself a clear, compelling, specific vision for your dating life that gets you excited and juiced.

I call this your Amazing Dating Outcome. When you lack this vivid vision, you lack direction and motivation, leading to loneliness and, in your case, low confidence and even weight gain.

This is the problem with New Year’s resolutions, which have an 80 percent failure rate. (Most people quit by mid-February.) You feel PUSHED by sheer willpower. But you need to be PULLED by excitement to achieve a great goal.

When you know exactly what your outcome is, even when you get off-track, you know your destination and can correct course. When a jet takes off from JFK for a coast-to-coast flight, it strays from its intended flight path much of the time, as the pilot adjusts for turbulence and other planes. But it lands at LAX right on the white stripe.

Your Amazing Dating Outcome should have three elements.

1: It’s amazing to YOU. It excites and juices you.

2: It’s measurable (examples: “two dates weekly”; “get a sweet girlfriend I love by the holidays”).

3: It’s an outcome—a place of arrival.

To turbocharge your Amazing Dating Outcome, know your WHY—the deeper reasons you want to achieve it. What will your outcome let you feel or give? How will you grow?

A strong WHY gets you in touch with your deeper purpose, fueling you to massive action. (At the same time, understand that life-changing results will take time. Your love life is like an ocean liner—there’s a lag between turning the captain’s wheel and changing course.)

Here’s an example of an Amazing Outcome from my client Brad: “To overcome approach anxiety so that I can meet women at night in the bars and also in the daytime. I would like to date around for a while and then choose a great girlfriend based on who I connect with the most. I would like to be in a relationship in six months or less.”

His WHY: “It’s about feeling more confident and attractive, knowing I didn’t settle. Also, I love being a boyfriend and having that companionship.”

Flirty Deeds

I’m single again, and I’m trying to flirt with women I talk to in my local coffee shop, but it’s not going well. I went up to one woman and said, “You are the most beautiful creature I’ve ever seen.” It didn’t work. Got any flirting advice?

—Chaz, 36, Atlanta, Ga.

deep questions to ask a girl. How to flirt

Don’t call a woman a creature—unless you meet in a black lagoon and she has gills.

Here’s the thing: There’s a fine line between flirting and fawning, and it sounds like you’ve been fawning over women, not flirting with them.

An easy mistake to make is fawning—being too impressed by a woman too quickly. Such comments might include, “You are just so amazing,” “I’ve never met anyone like you,” and “Wow, you are so beautiful!” Those things are fine to say after the two of you have made a genuine connection.

But if you lay it on too thick too soon, you can come across as her groupie, not her equal. That’s a big turn-off because  it makes you seem “beneath” her. And no one wants to date beneath themselves.

So don’t fawn. Flirt. I define flirting as showing a woman that she’s affecting you but in a casual, no-big-deal way. This makes her feel sexy and attractive, without putting her on a pedestal.

Here are examples of being affected by her but not fawning over her.

To see a master flirt in action, watch clips of comedian Craig Ferguson on his old CBS talk show, “The Late Late Show.” Whenever a beautiful starlet was his guest, he always let his attraction show with humor and class, and he never fawned.

Want some tips on what to say when asking a girl out or where to go on a first date? 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 such as how to get out of the friend zone. 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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Flirty Questions To Ask a Girl

Dating coach Connell Barrett on flirty questions to ask a girl, why rejection is no biggie, and how to get a second date.

Flirty Questions To Ask a Girl

It keeps happening. I always hear, “You’re great, but… I’m just not feeling it.” My first dates seem to go well, but it rarely leads to a second date. I think I need to be better at flirting. What are some flirty questions to ask a girl in those first few dates?

—Bradley, 41, Ottawa, Canada

The best flirting arises in the moment, but if you want a cheat sheet of pre-planned questions to help you dial up the romantic tension, here’s some help. Here are five flirty questions to ask a girl.

“What’s the sexiest place you’ve ever visited?”

Everyone likes talking travel, but some destinations are sexier than others. (There’s a big difference between Paris, France and Paris, Texas.)

Free to tack a cheeky joke onto the end of the above question: “What’s the sexiest place you’ve ever visited? I mean, since you haven’t seen my apartment yet…”

“What celebrity do you think would be best in bed?”

This gets you both thinking about S-E-X, but without you having to ask in a vulgar way.

“What’s one thing you want to ask me but are too nervous to?”

A superpower question! This gives her permission to ask you something personal or intimate, and when you’re both being more vulnerable, it can heighten romantic connection.

“How old were you when you first felt those, you know, feelings?”

It can be intimate and bonding to talk about how it felt when the hormones kicked in. Pro tip: Go first, to see how she responds. I’ve said this on a date or two: “I pretty much began puberty when watching Jennifer Beals in Flashdance. Legwarmers still drive me crazy.” By leading the conversation, you give her the green light to open up.

“What’s something exciting you’re dying to try?”

Save this question for well into the date, after you’ve both loosened up. She may hit you with a sultry answer (“I think it’s pronounced, ‘ménage-a-trois’…”). But hell, even if she says pizza-bagels, don’t worry. She’ll send the same question your way, and you say, “Do you want my G-Rated or R-rated answer?”

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The Life-Changing Magic of Getting Rejected

Arrg! I constantly see women I want to approach, and no matter how hard I try, I can never man up. Help! How do I smash through this?

—Seth, 39, New York City

man with tie - flirty questions to ask a girl

I know how it feels to want to approach a beautiful woman yet not be able to. It can feel like there’s an invisible force field that you just can’t break through.

I wrote on how to beat approach anxiety. Literally.

My new book is called Dating Sucks but You Don’t, and what “sucks” more than anything? Rejection.

Dating sucks because rejection sucks. You take a chance with your heart—you ask a girl out, you send that flirty text, you approach—and if you get turned down, you feel wounded.

But what causes the pain is not rejection itself? It’s how you interpret it. You give it a painful meaning. You turn it into evidence that you’re not attractive to the kinds of women you want to date.

You see, all men (and all people in general, really) want to feel special and important. This driving force is hardwired into our psyche. It’s why we climb mountains or pump iron. Hell, I wrote a book in part so I can tell the world, “I’m an author, bitches!” It makes me feel cooler.

One of the most powerful ways to feel special and important is through dating. Validation from the right woman can be intoxicating. It helps you realize something powerful: You are enough. And there’s nothing wrong with this.

But when you get rejected, it can make you doubt your romantic worth. You feel less special, misinterpreting that rejection as a sign that you’re unattractive. Then you extrapolate: If you’re not attractive to women, if you’re not enough, then maybe you won’t get to give or receive love, and that would lead either to loneliness or to settling—both awful outcomes.

That’s heavy stuff.

Viewing rejection through this lens turns any romantic risk into Judgment Day for your worth as a man. So you don’t take risks and approach the kinds of girls you’re drawn to, because rejection would cut deep, making you feel unattractive and less of a man.

And if you DO take a chance and, say, approach a woman you find attractive, you can’t relax and be your best self, which leads to MORE rejection. It’s a vicious downward spiral.

I want you to see rejection through new eyes.

When I take a client out for in-person wingman training, I WANT him to see me get rejected. I have him choose a scary approach situation—say, a large group of girls on the dance floor—and I go in, talking to the cutest one.

I often (but not always) get rebuffed. I do this not because I’m a masochist. My client needs to see rejection not as something to fear but as part of the dating process. It’s required.

You can’t approach women and NOT get turned down from time to time. You can’t get Tinder matches and NOT get ghosted occasionally. It’s part of putting yourself out there.

What if you saw rejection as painless? What if you were immune? What if you gave far fewer fucks? You could take new, bold actions and with lots of confidence.

I want you to see rejection for what it is: no biggie. A woman’s rejection is not—I repeat, NOT —evidence of your worth or importance. It’s merely evidence that she’s not interested. Maybe you’re very attractive but just not her type.

Rejection means next to nothing. You can brush it off, just as you do when the restaurant hostess “rejects” your request for a brunch table on a busy Sunday, or when the Delta ticket agent “rejects” your request for a business-class upgrade.

Look at dating rejection the same way. Your worth isn’t on the line. It’s not personal.

The truth is, a woman who barely knows you can’t truly reject you.

Now, if your girlfriend says, “I don’t love you, you’ve never made me orgasm, and I’m leaving you for Fabio,” okay, now THAT is rejection.

But if a woman you barely know blows you off, she may simply be saying she likes the Beatles, and you’re the Stones. No shame there. The Stones flippin’ rock!

How To Ask For a Second Date

Are there any differences in how you ask for a second date by text, as opposed to in-person?

—Cody, 33, Biloxi, Miss.

how to ask for a second date

In person, you want to let your emotions inform the words you use to ask her out. With texting, you can craft the precise, flirty message you want to send.

Here are five text messages you can send after a date, ranging funny to sincere to cheeky. Each one lets you ask for a second date with charm.

Want some tips on how to get more swipes on Tinder or what to say when asking a girl out? 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 has been called one of the best dating coaches in the world. He's appeared on talk shows such as Access Hollywood and The Today Show. He's also been published in magazines such as O Magazine, Maxim, Cosmopolitan, and more. Connell helps men get out of the friend zone and find the women of their dreams. Ask Connell a question below.

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Where to Go on a First Date

Dating coach Connell Barrett answers your questions on where to go on a first date, why “alpha males” aren’t a thing, and the dating-app opener that never fails.

Where to Go on a First Date

Now that the pandemic is ending—I hope!—do you have any tips on where to go on a first date? My go-to date is dinner, but that gets expensive.

—Devlin, 27, Birmingham, Ala.

OK, pop quiz! Which of these first-date propositions sounds more inviting?

A) “Hey, how about a couple glasses of wine and some stimulating conversation?”

B) “Hey, how about an elaborate, three-hour, white-tablecloth dinner where we sit across from each other, struggle to hold a conversation, and try not to make weird chewing noises?”

Ding, ding! If you picked “A,” you’re correct! The more fun and low-stress you make the date sound, the more likely your potential partner will be into it. Drinks are a classic option, as is coffee, smoothies, or ice cream. Activity dates like bowling, karaoke, or trivia nights can also be a blast and give you built-in stuff to talk about.

For first dates, stay away from doing dinners—they’re too expensive and time-consuming, and you’re liable to feel stuck if there’s no chemistry. No movies or group dates, either. Make it just the two of you.

Avoid big and elaborate gestures as well. No gifts, poems, or standing outside her window with a boom box playing Peter Gabriel songs. That kind of rom-com stuff reeks of desperation. (There’s an Onion article titled, “Romantic-Comedy Behavior Gets Real-Life Man Arrested.” There’s a reason for that.)

Remember that the most important thing to do on a date is to have fun together. So, ideally you want to choose an activity that you really enjoy doing and at the same time, allows you to connect.

For a LOT more first-date ideas, check out my new book, "Dating Sucks but You Don't."

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Am I Alpha Enough?

I see a lot of videos and articles about how women want to date alpha males. Is that true? What if I’m just not an alpha guy? Is there hope for me?

—Barnes, 47, Boston

where to go on a first date. No alpha males

There’s no hope for you. Sorry. Forget your hopes of finding a soft, warm girlfriend—unless she’s inflatable.

I kid, Barnes!

I was once in a BO-drenched Las Vegas conference room, watching a strutting “pickup artist” on-stage praising the supposed panty-dropping powers of being a dominant man. “The Alpha male gets all the tail,” he said with Johnnie Cochran flair.

But there’s a problem here: Alpha males aren’t a thing. It’s a big old myth.

The idea of the alpha male first gained credence in the 1970s when wildlife biologist L. David Mech, an expert in wolves, published a book that documented the existence of alpha wolves in the wild. Two decades later, he tried to replicate his findings, but he couldn’t.

He was horrified. It turns out, the “alpha” behavior he thought he’d observed was simply mom and dad wolves caring for their pups. Mech renounced his original findings, but it was too late; the myth of the alpha had cemented into conventional wisdom.

It’s also informed a lot of bad dating advice. There’s no concrete, scientific evidence for “alpha males” getting to mate with all the females—in any animals, including humans.

Take our close relatives the chimpanzees. Studies show that the aggressive chimp doesn’t necessarily become the group leader, and that smaller, more docile chimps become dominant by completing more feminine tasks, such as grooming other chimps. And our closest biological relatives are bonobos, apes that live in a matriarchal society. (Humans and bonobos are the only species that French kiss.)

Traits like assertiveness, courage, and boldness are absolutely essential in dating. A woman must sense your strength. But the idea of the alpha male is a myth, and a troublesome one.

At worst, alpha-male behavior stifles growth and encourages men to view women and “beta males” as inferior. At best, it leads to wearing Axe body spray, chest bumps, and saying things like “brah” and “baller.”

Reject the “alpha” mask. It just doesn’t work, plain and simple. Yes, there are times when you must take decisive action, “man up,” and make a move. But studies show that non-alpha qualities like kindness and generosity are the key indicators of fulfilling relationships.

Knock-Knock. Who is There? A Great Opener...

My openers on Tinder rarely get a reply, and it’s driving me nuts! Any all-purpose openers that you can recommend? I’m so tired of getting all excited by matches, and then never having the women reply to me.

—Max, 23, Utica, N.Y.

date app opener

Behold, the dating app opener that (almost) never fails. It’s two simple words that we all know from childhood: joke-telling.

Knock-knock…

I know, I know. This shouldn’t work. But the knock-knock opener is super effective because it’s both playful, and it creates curiosity. Plus, we’re all conditioned, Pavlov-style, to reply, “Who’s there?”

The cheesier the joke, the better. I like this one, myself.

Knock-knock.

Who’s there?

Nobel.

Nobel who?

No bell! That’s why I knocked.

She will groan, and possibly mock your joke selection. But she WILL write you back.

Want some tips on how to get more swipes on Tinder or how to talk to women? Read Connell's column here and subscribe so you never miss an update!

Connell Barrett is a dating coach from NYC that specializes in actionable advice for men. He helps men all over the world find their dream woman. In fact, he's been called one of the best dating coaches in the world. Connell's dating advice has appeared in Maxim, Cosmopolitan, and more. In addition, he has been featured on Access Hollywood and the Today Show. Ask Connell a question below!

Ask a Question

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The Secret to Finding the Right Woman

Dating coach Connell Barrett answers your questions on the secret to finding the right woman, how shorter guys can connect with women, and an easy way to feel more masculine.

The Secret to Finding the Right Woman

Your tips on dating with courage, action and authenticity has changed my life! In fact, I’ve gone from settling for so-so women, to dating “Amanda.” She’s amazing—smart, sweet, beautiful, and we have such a deep connection. I think I’ve found the right woman for a LTR. But how do I know for certain?

—Brett, 36, Denver, Colo.

Nothing is certain in life, except for death, taxes, and sucky Adam Sandler movies.

But there’s a way to be pretty darned sure.

I’m stoked to hear that you’re no longer settling. The truth is, every potential relationship falls into one of four categories, depending on where you are in your search for love. Here they are, from worst to first, as laid out in my new dating book, Dating Sucks but You Don’t.

Wrong Person, Wrong Time: This is when she’s not a good fit for you, and you don’t even want a relationship. But dating sucks, and you don’t want to be alone, so you relent. The ultimate in settling.

Wrong Person, Right Time: You’re ready to commit to someone, but you have a scarcity of options, so you settle for what you can get. This is most men, I believe.

Right Person, Wrong Time: You weren’t looking for romance, but how could you not lock down such a dazzling woman? She’s awesome.

Right Person, Right Time: She’s the whole package—brains, beauty, kind, and is cool with your bad-movie marathons and likes your dorky friends (OK, that last one is just for me.) She turns you into a human heart-eyed emoji, and you’re ready to dive in for a LTR. This is the ideal.

As men, deep down we all want true love, but we tend to settle for something comfortable and convenient. Something “good enough.” But when you settle, you miss out on finding the right person.

Don’t settle for “good enough.” You want to raise your standards and go after a truly great relationship with a quality woman who is right for you.

If you feel like a woman might be the right person at the right time, ask yourself three important questions before pursuing a relationship.

1: Do We “Just Fit”?

Do your souls dovetail? Do you just fit? Listen to your gut.

2: Does Our Big Life Stuff Align?

Are you compatible in areas such as core values, wanting a family, religious views, political beliefs and cultural backgrounds? Granted, you may only want a girlfriend right now, not a wife, but a great relationship should have strong long-term potential.

You could have lots of “stuff” in common, but to make it work in the far-off future, you need most of Your Big Life Stuff to align, or else you could hit huge roadblocks.

3: Will We Grow Together?

Can you see the two of you blooming together, complementing one another? Because if a relationship isn’t growing, it’s dying. There’s no in-between.

If you answered a hard “no” to any of these questions, there’s a chance you’re not with the right person. Remember, you’re a Radically Authentic guy with an abundance of dating options. Never settle.

If you answered “yes,” then you may be ready to get exclusive and, in time, go all Beyoncé and put a ring on it.

finding the right woman

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The Highs and Lows of Being Short

I’m 5-foot-5, and my height hurts my confidence when I’m out meeting women or when I go on dates. I know that women like tall guys, and I’m not one of them. Can a shorter guy do well with women?

—Richard, 41, Philadelphia

I’m about 6-foot-2, but back in the day I felt about 2-foot-6, because my confidence was so low. Being tall is a nice bonus, but it’s hardly a magic pill.

One of the biggest myths about dating is that short guys aren’t attractive to women. But the truth? Women like guys of all shapes and sizes.

Dating is about connection and giving your best, truest self to another person. Do those things and you can have an abundance of romantic options. You can land a great girlfriend, whether you’re six-foot-four or four-foot-six.

Women don’t necessarily want tall guys. They want guys who aren’t shorter than them. The average American woman is five-foot-four, so if you hit that spot or above on the tape measure, you have lots of options.

And yes, you can also attract girls who are taller than you. For a woman, it’s not really about a guy’s height. It’s about how a guy’s height makes her feel: namely feminine, smaller, and safe. A shorter man can give her those same feelings by adding muscle at the gym, carrying himself with confidence, using his voice in a dominant way, or getting great at flirting.

Here’s a tip: Feature what you can’t fix.

In business, there’s a marketing concept that says, “What you can’t fix, you feature.” By highlighting a products' weakness, you turn it into a strength. In golf, a nine-holer isn’t a lesser track; it’s an “executive track.” A car isn’t too expensive; it’s a “luxury automobile.”

If you’re shorter than average, you can joke about it, turning it into a signifier of confidence.

I once went out for the night and found myself wing-manning with a cool, five-foot-four guy named Darren. He was phenomenal with women—way better than me at the time.

Not only did he not care about his height; with several girls he met, he led with it. He told one woman, “When we get married, I can be on the wedding cake,” and she laughed so hard, she spit out her drink. To another: “I promise, I’ll never look down on you.”

But what really made him so magnetic was that he decided he was gonna give fewer f*cks about his height.

So feature what you can’t fix. It tells people that you’re secure in who you are. And that kind of confidence is sexy to women of all heights.

dating advice for short men

No Apologies

It’s really hard for me to make a move. I can’t go for the first kiss. I can’t tell a woman she’s sexy. I’m afraid she’ll think I’m creepy or weird. I’m lonely, and I want a relationship, so I feel stuck. Once, this woman I know invited me to spend the weekend with her. We even slept in the same bed—her idea—and I never made a move. Help! What’s wrong with me?

—Douglass 47, Sacramento

There’s nothing wrong with you, Doug. You’re good! I’ve been exactly where you are.

It sounds like you have an inner conflict: One foot is on the gas, but your e-brake is on.

The source of your inner conflict? On one hand, you’re looking to date a great girl, so you want to “make a move,” in the right situation. But you fear that if your move is rejected, a given woman will see you as a creep, perv, or weirdo. Feeling that way would hurt, so you avoid taking risks—but at a steep cost… loneliness, lack of love, and crushed confidence.

You need to buy into the fact that you’re a man with desires and needs. There’s nothing wrong with trying to meet those needs—as long as you respect woman, of course.

Our job as men is to lead and take action and, in dating, make some moves now and then. And it’s the job of women to say yes or no. And either answer is 100 percent OK.

Here’s a mantra I want you to say out loud—with strong, resonant vocal tonality—five times a day for the next month. Repeat after me: “I’m a man, I have desires, and I make no apologies for them.”

Internalize this new belief every day, and you’ll soon feel less afraid of “making a move” on dates because you’ll buy into doing your job as a man.

Want some flirty tips first date tips  or dating tips for shy guys?  Struggling to get women to chase you? Read more in Connell's column and subscribe so you don't miss any updates!

_______________________________________________________________________

Connell Barrett is a NYC dating coach for men. He specializes in helping men date with authenticity and provides advice on finding the right woman. Connell has a new dating book coming out Spring 2021 and has appeared in print many times. He's been featured in several publications, including Cosmopolitan, Maxim, O Magazine and others. Furthermore, he also appeared on the Today Show and Access Hollywood. Ask Connell a question below!

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After a Second Date, Now What?

Dating coach Connell Barrett answers your questions on third-date strategies, unlocking true confidence, and how to approach in a NON-creepy way.

 

After A Second Date, Now What?

I’m good on first dates, but then I’m not sure how to play the second or third date. I seem to lose a woman’s interest right before we start dating exclusively. It’s a problem because I’m 40 and I want to settle down with a great girlfriend. But I can’t get past date 3. After a second date, now what?

—John, 40, Los Angeles

 

Such a great question: After a second date, now what? I’ll bet you’re putting too much pressure on yourself on the third date.

The stakes are higher on date no. 3 because it’s the gateway to a relationship. Date 1 is about seeing if there’s chemistry and mutual attraction. On the second date, you get a sense for how comfortable the two of you are together. And on Date 3, you decide if you’re a good fit long-term.

Think of the first few dates like a series of job interviews: By the third, you’ll both know if you want the “job” of being in this potential relationship.

The stakes are higher, but you DON’T want to try too hard to be more impressive.

Repeat after me: To impress, do less. I don’t mean not to try. Just don’t strain too hard. Many guys feel the need to “up their game” on big dates—to plan elaborate activities or spend a bundle at a white-tablecloth restaurants. This can backfire because trying too hard conveys neediness. That kills romantic connection and attraction.

Don’t try harder. Go deeper. On the third date, try to connect over Big Life Stuff: careers, religion, wanting kids, politics, your core values. When you and your date find that your Big Life Stuff aligns, it’s easier to move toward becoming boyfriend-girlfriend.

Also, make sure that the woman you are dating feels a sense of progress—that every date is taking things further along.

There should be no rush to score, but you do want to be circling the bases. If there’s no physical connection by Date No. 3 (a good make-out, at least), something is off. Either it’s a lack of chemistry, or someone is not making moves—likely, you.

Many men get stuck on the same base for multiple dates. If you reached first base on date no. 1 and are still there two dates later, it can lead to the “friend zone.” The other person doesn’t feel things are progressing, so they lose interest.

In terms of physical connection, try to keep moving forward. The pace around the bases doesn’t matter. You can be Rickey Henderson or Big Papi. It’s all good, as long as you’re not stalled on first.

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Crisis of Confidence

how to gain confidence

Connell, I feel so down on myself. I’ve only had one real girlfriend my whole life, and she dumped me. Most of the women I’ve been intimate with, I had to pay. I mean escorts. I’m so lonely, and sometimes I wonder if I’ll ever find someone who loves me for me.

—“John,” 44, Dallas

 

John, thank you for sharing in a vulnerable way. That kind of candor takes real strength, and I honor you for it.

I know exactly how you feel. I used to feel unattractive to women. Girls just didn’t like me in high school or college. And when I finally met the rare woman who wanted me, I married her—and she dumped me nine weeks later.

It was over so fast that we could have fought for custody of the wedding cake.

As I drove away from her house in my red Honda Civic—the backseat loaded with unwrapped wedding gifts to be returned for store credit—I felt rejected by an entire gender.

I would soon hit my low point. I paid for sex, too. I went to escorts and massage parlors. I was ashamed. In my mind, I was unworthy of wonderful women, so I had to pay them to be with me. While my friends were getting engaged and coupling up, I was in seedy hotels handing strangers envelopes full of cash, fearing arrest and feeling terrible—all for scraps of intimacy. My self-esteem was at rock bottom.

Finally, I said, “Enough!” And I went off on a decade-long path that transformed me from lonely and dateless to an international dating coach.

Here was the first step I took, and I want you to do it, too.

Take a sheet of paper, and write your “Awesome List.” Write out at least 25 reasons why you’re a GREAT choice for women.

To start to rebuild your confidence, you must get clear on what you OFFER women, rather than telling yourself bullshit stories of all the things you THINK you lack.

Don’t overthink this list. Under-think it! Any reason is good enough. Your 25 reasons should focus on ANYTHING, great or small, that you have to give. Maybe you speak a second language, or you can cook, or you’re well-traveled, or are a good son or brother. Perhaps you’re funny, smart, sweet, and have a good job or are working on getting a cool job.

Confidence comes from the inside. And guess what: Women LOVE confident men.

So write out 25 reasons why you’re a great choice for women, and you’ll notice how much better you feel when you focus on what you offer, rather than on what you THINK you lack.

Get writing!

 

 

How to Never “Run Out of Things to Say”

after the second date, now what? Couple holding each other

I get stuck in my head when talking to women, either on dates or out socializing. How can I keep conversations going in a way that women like, without choking under pressure?

—Kevin, 29, Athens, Ga.

 

How to not run out of things to say—it’s one of the biggest problems single guys face. “What do I say? What are the right words?”

Here’s what to do.

Make a shift. Lower the bar for how good your conversation has to be. You’re not giving a TED talk or doing a stand-up act. You’re talking to a woman. Your words don’t need to be amazing. They just need to be honest, authentic thoughts from the real you.

You likely think that every word has to be witty and clever, but you’re already cool and charismatic enough. You are already an authentic man of value.

So lower that conversational bar. In fact, I give you permission to be borderline boring. I’m not saying TRY to be boring. Just lose the “I Must Be Amazing” filter and let the words flow without overthinking them or judging them.

Free-associate and speak AUTHENTIC thoughts. If you’re talking to Super Hottie at the Party, and your mind is thinking, “Wow, she’s hot, and I’m kinda intimidated,” then THAT is what you say.

Tell her, “Hey, can I be honest? You’re just hot, and pretty girls intimidate me. Anyway…”

This kind of authenticity and vulnerability is mesmerizing to women because it’s rare, and it takes so much courage. Bonus: It will relax you because you’re not holding back. You’re putting your best, more real self on the line.

Don’t try to make your words perfect and amazing because it only creates tension. That makes it harder to connect.

You know who women find amazing? A guy who’s not trying to be amazing—rather, he’s expressing his best, most authentic self and thoughts.

 

___________________________

Connell Barrett is a NYC dating coach for men. He specializes in actionable advice to help men all over the world find their dream woman. Barrett's work has been featured in Maxim, Cosmopolitan, and more. Look for Connell's new book coming out Spring 2021.

 

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How To Get Women To Chase You

Dating coach Connell Barrett answers your questions on how to get women to chase you, escaping the friend zone, and what to text when a girl goes quiet.

How to Get Women to Chase You

It seems like I’m always the one who’s asking women out, making moves, and chasing after the girls I want to date. I really want to know how do you get women to chase you?

—Charles, 37, Seattle

How to get women to chase you? Simple. Flip the script and make HER the seducer.

This is a fun, effective, win-win technique that shifts the normal “boys chase girls” dynamics, and that lots of women love because it gives them the power.

A great way to do this is to misinterpret an innocent comment as “evidence” that your date wants to seduce you. It's sort of reverse psychology to make her chase you instead of being like every other guy she's talked to. By accusing her of objectifying you, you give her all the agency, and you subtly tell her, “I’m not like those guys.” Also, it takes things from a logical, friend-to-friend context to a romantic, flirty one. And it’s just a blast. For example:

HER: “I recently redid my bedroom...”

YOU: “Listen, I’m not going to bed with you tonight. I know I’m sexy, but we just met, so let’s take it slow.”

Look for opportunities to say the kinds of things to women that women always tell guys. (As a joke! You’re not actually accusing her of anything.) Such as…

Bonus: Some women enjoy this role-reversal so much that they fully commit to the seducer role, insisting that you go back to her place, or that you take her to yours. And, well, it’s just not gentlemanly to say no to a lady.

Escaping the Friend Zone

how to get women to chase you. Escape the friend zone

How do I escape the friend zone? I don’t get many dates, and then I always get that next-day text: “Hey, you’re nice, but I’m just not interested in dating you.” That hurts my confidence.

—Caleb, 23, Nova Scotia

The friend zone has tortured more men than thumb screws. And I feel your pain. I didn’t just live in the friend zone. I was the mayor, and my face appeared on currency.

I had countless first dates that went nowhere, and it sucks to get that “I’m not feeling it” message, especially if you thought the date went well.

So let’s fix that. Here’s how to escape the friend zone on first dates, but also when you’re texting and messaging women or having a video or phone date.

It takes courage, but it’s simple. All you need to do is tell her—in an authentic, real way—something that you find sexy about her.

And I want you to use that word: sexy.

Don’t fake it. Let it arise from a real place. That little voice will tell you, “Wow, she’s so witty or funny or cool. That’s sexy.” Tell her! Yes, even if you’re scared.

This sends her a clear, confident message that lets her know, “I’m not here to be ‘just friends.’ I want more.”

This is who you need to be, OK? A real, authentic man who has the cojones to show his romantic interest in a charming way. This lets her know that you’re interested, and that you have the courage to be real and vulnerable.

If you’re asking, “Won’t this be creepy?” No, not if it’s a QUALITY that you find sexy about her, rather than a part of her body.

Don’t get me wrong: A woman wants to be seen as physically desirable. But complimenting her legs or lips or looks is what most guys do.

You’re gonna be the rare man who sees her inner sexiness, and women love that kind of guy more than I love Broadway show tunes.

So, on your next date, notice her inner hotness—her wit or presence or quirkiness—and say something like, “Wow, I love your [quality]. It makes you super sexy.”

Tell her she’s sexy, and you’ll escape the friend zone once for and for all.

All Quiet on the Texting Front

Be confident

It’s so frustrating. A texting exchange is going great, and then… nothing. Total quiet on her part. I don’t get it! What do I do when a woman I’m messaging with goes quiet?

—Derek, 30, Vancouver

I know, it can make you scratch your head when a woman you’re messaging with just stops replying. Imagine how strange it would be if the same thing happened while you were talking to a cute girl at a bar, and in the middle of the a nice chat this happened.

YOU: “So anyway, how long have you been into skiing?”

HER:

YOU: “Did you hear me? We were talking about skiing.”

HER:

YOU: “Umm, are you OK? Why aren’t you talking? You’re just staring at me.”

HER:

YOU: “Am I on a hidden-camera show, or something?”

It would be weird A.F., right? But this happens ALL THE TIME with messaging and texting.

Why? Well, long story short: An attractive woman has a LOT of dating options, and if she gets distracted by other guys, she might go quiet on you. It’s not personal. It’s just dating in the Tinder Age.

What you don’t want to do is give up after one unreturned text message. Show some persistence, coupled with charm.

First, don’t write anything that sounds needy or try-hard. Don’t write, “Hey, did you get my last message?” or “Hey, do you like me? Should I stop messaging you?” Never send a message that conveys a lack of confidence.

Instead, send her a “value text”—something to make her smile. And it could be a totally different topic from the previous message you sent.

Let’s say you send a woman a message such as, “Hey, how’s your day?” She likely won’t reply because, well, that’s a boring message. It’s a cliché, and it doesn’t offer her anything.

But don’t give up. Remember: Texting is about giving her value. Send her a follow-up message that can make her smile. A meme or a GIF or a link to a song she might like—something of value.

Most guys are sending needy, boring messages that offer nothing. You should be the rare guy who makes her smile and laugh and feel good. And that will keep her writing you back.

Another technique is to simply change the topic. Forget that last, unreturned text message and send her something on a different topic. You might write, “OK, what was the coolest thing you did last weekend?” A new conversational thread shows persistence but not neediness or pushiness.” Bonus: It’s a GOOD question to ask because we all love talking about the cool things we’re doing in life.

Don’t mistake one unreturned message as you being blown-off: Try one or two more times with a “value text”—and notice how often women reply to your charming follow-up text.

________________________________________________________________

Connell Barrett is a NYC dating coach for men. He specializes in actionable advice to help men all over the world find their dream woman. Barrett has also appeared on the Today Show, Access Hollywood, and more. He's also been a guest on many podcasts along with his own podcast on how to get a girlfriend. Connell has a book called Dating Sucks But You Don't, available here.

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

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