How to Get a Girlfriend with Connell Barrett - Ask the Dating Coach: ‘How Do I Start Conversations with Women without Making It Awkward?’

Episode Date: November 19, 2025

If you struggle to start conversations with women, this episode of “How to Get a Girlfriend” will help. While taking questions, dating coach Connell Barrett gives you a simple, reliable ice-breaker you can use anywhere to talk to women—without it feeling awkward. He also reveals how much height and looks actually matter to women (hint: not much!). And you won’t believe what one guy is willing to do to his body to become taller.Episode Highlights:01:32: “Connell, How Do I Make Women Chase Me?”08:25: “How Do I Start Conversations without Making It Awkward?”11:55: “What Actually Makes Women Attracted to Men?”17:30: “How Important Are a Guy’s Looks to Women?”22:57: “Should I Get Leg-Lengthening Surgery to Become Taller?”DO YOU WANT TO ATTRACT YOUR DREAM GIRLFRIEND? BOOK A FREE CALL WITH CONNELL TO LEARN ABOUT 1-1 COACHING: http://www.DatingTransformation.comEMAIL CONNELL FOR A FREE COPY OF HIS NO. 1 AMAZON BESTSELLING BOOK, "DATING SUCKS BUT YOU DON'T": [e-mail]

Looks don't really matter all that much to women. Good looks are like jacuzis and dating. They're nice to have, but they're way overrated. Welcome back to the How to Get a Girlfriend Podcast. I am your host, dating coach, Connell Barrett. I am here to help you flirt with women confidently, get more dates, and get a great girlfriend. and date with authenticity, do it all with integrity and authenticity, showing women the true best you. No sketchy pickup artist moves needed. Today I want to help you solve a couple of very common

problems that men struggle with, such as how do you start a conversation with women in real life without making it awkward? I'm going to help you do that. And if you've ever wondered, how do I get women to chase? What do women chase? How do I get a woman interested in me? Well, I'm going to help you with that as well. Because today we're going to play an episode of or do an episode of Ask the Dating Coach. I get a lot of questions from good guys like you, inquisitive guys who just want help. And so I've taken five or six of the most interesting, pressing, and in one case, jaw-droppingly, shocking questions. And I'm going to help answer, I'm going to help you in your dating life by answer.

answering these questions. So let's get right to it. Let's play a little bit of Ask the dating coach. The first question comes to me from Jason on Instagram. Jason says, hey, Connell, how do I make a woman, quote unquote, chase me? I see a lot of social media content about how to do this, how to say that to get a woman to quote, chase me. What's your take on this? What's your advice on how to get a woman to show interest and pursue me? Seems like I'm always the one chasing women, always pursuing them. I want them to show interest in me. Hey, Jason. Okay, if you want a woman to chase you, steal her purse.

Just make sure that you're wearing really good running shoes. Okay, enough dad jokes. So one of the biggest myths in dating and one I'm so tired of hearing about is this idea that you can make a woman quote unquote chase you just with certain lines or by tactical, in tactical ways, like playing it cool, wait two days. to message her, play it cool, use tactics, but none of those will work in and of themselves. Tactics, lines do not make a woman chase a guy. Okay, Jason, what women chase is value. A woman will chase, quote unquote, chase, show interest, pursue a guy if she sees a lot of romantic value

in you. Basically, it's what you can bring to her dating table. And if she doesn't perceive you as bringing that to her table, then she won't pursue you, no matter what you say or how tactically compelling the mobs might be. So I want you to ignore all of those pickup dudes, the male quote-unquote experts, most of them don't know jack shit, who say, say this to get her chasing you. Do this to get her chasing you. None of that's going to work. Women don't chase lines and tactics. You can use the best lines in the world, but if she does not see you as somebody who adds something meaningful to her love life, she won't chase you. You'll just come across as weird and unrelatable, or she'll ignore you. But the reverse is also true when a woman

does see real value in you, when she can see you as boyfriend material, or you're the kind of type of guy she wants to have a date with or you make her laugh you bring value to her love life then yes a woman will pursue she will show that interest she will quote unquote chase you to an extent and this is really this really comes to life uh with online dating it's a good way to see chasing or not chasing happening when you have a really good profile when you have photos that show your most attractive self, good style, good portraits, a photo that shows you leading an interesting life, then that's what a woman might chase. For example, I have a client, I'll call him Mickey. Mickey, we overhauled his profile. We got a couple of really good portraits where he's

looking he's dressed well he's looking as handsome as he can look not a male model but you know we're working with what we have and he's got handsome qualities good style great portraits some photos of him playing guitar he loves to play guitar so he's got a little bit of a of a artistic lead guitarist energy that's valuable to women women are often chasing quote unquote chasing Mickey because they see what he brings to their dating life. It's not because of the things he texts them. It's not because of any moves. They're chasing value. We all chase things that we value. That's what we chase. So that's why guys like Mickey, and sometimes me, every so often on the dating apps, I'll have a woman message me first. How would you like this opener from the dating apps?

A woman message you first, and for her opener, she gives you her phone number and says, hey here's my number you should call me or you should text me i'd like to meet you that's chasing and it's not a egotistical thing i don't i don't even like the word chase i'm only using it because jason asked is used that phrase in his question i hate this idea of making women chase no we pursue things in life that have value to us so i want you to make your profile or make your whole dating presentation on a first date when you approach online dating Make yourself so attractive, so authentically attractive to women that women who like your type are going to pursue you show that interest, or at least make their interest known. But man, that was an amazing aha moment I had back many years ago when I realized, okay, I've got this version of my profile that makes some women literally send me their phone numbers right away, or at least very quickly, sometimes without even me asking.

So I want you to unplug Jason from the games that these so-called dating experts do on TikTok, on YouTube, on Instagram, do this tactic, do this trick. Women don't chase based on tricks. They chase based on value. So stop focusing on tactics and start focusing on becoming even better, maybe an even better profile. Or if you want them to, quote, pursue you, show that interest. after a date become even better, more valuable on a first date, more grounded, better at flirting, secure in who you are? That's when women show interest. Because when you show women that real

high, quote unquote, high value version of yourself, the chasing will take care of itself. And I wouldn't use the word chase at all, but when my girlfriend, Jess, and I had our first date, the very next day I remember being so nervous. I was like, I hope she likes me. I hope she wants to see me again. And I opened my phone. I turned it on. I was like, oh, did Jessamine write me? And she had. And she told me what a good time she had. And she basically let it be known that she wanted me to ask her out again. She called me suave. And that made me feel so good. And the reason is not because I did any tactics. My first date with my now girlfriend was tactic-free. Everything was about chemistry, fun, light, banter. And essentially,

she saw in me, oh, this guy has real value to bring to my love life. That's why she showed that interest. That's why I chased her while she chased me just as much. Okay, next question comes from Ken in Chicago. Ken writes Connell, I'm shy. How do I start conversations with women in real life without being awkward. Ken, use my what-to-say method. I call it the what-to-say method. Three reliable ways to start a conversation with any woman anywhere with little-to-no awkwardness, and you can do it in a very spontaneous way. Plus, you don't have to remember any scripts. It's basically rejection-proof and zero-percent creepy. So here's my what-to-say method. It's, think of it as in three parts.

You see a woman out in the world, a bar, a coffee shop, your gym. Give yourself three options, A, B, and C. So you look at her, you read the room, so to speak, and think, okay, option A, give her a G-rated compliment, something light, such as, hey, you have really great style. Or maybe she has an awesome tattoo. Hey, I really like your tattoo. You have great choice, great choice in tattoos. That's option A. option B ask an appropriate question based on where you are and make it contextual so for example

let's say you're at a coffee shop you might say to her hey excuse me are you going for ice coffee today or hot coffee she's not going to reject that 99% of the time that will not be rejected because you're asking a normal question not a weird creepy one what is she going to say how dare you ask me what kind of coffee I'm getting here at Starbucks. If she does that, she's the weirdo, not you. And option C is you make an observation and you call out that observation. So you notice something slightly unusual about her or the environment and you comment on it. So for example, let's say you're at a bar and you see that a woman and her friends are all drinking the same red, fruffy, fruity cocktail. You might say, hey, you guys have matching drinks. Interesting.

what's the story there? You're asking her why all their drinks match. So you're looking for something slightly unusual or a detail that jumps out at you. That's how you grab an observation. So again, A, B, C, A is you give a G rated compliment, B, ask a question that's appropriate, and C, you make an observation and you call out that observation. And these three options work because they're simple, they're normal, they're appropriate, they're socially normal, they're non-creepy. You'll always know what to say. And you won't have to plan it and you don't have to, you don't have to memorize it. You don't want to go through the world memorizing things to say to women. That's how you run out of things to say is running out of memorized material.

You just simply go with A, B, C. Quick, quick example from my life. I met my now ex-girlfriend, but at the time, this was me approaching her. My ex-girlfriend, Donna, I met her at Barnes & Noble. She was in the business books section. I just walked up, and I went with option B, ask an appropriate question. And I said, hey, how's your search going for the right business book? That was the first thing I said to her, and we were on a first date. One night later, two nights later, I think, all began with me just choosing that option.

It's as simple. It's as easy as A, B, C. You struggle with dating, right? Sure, you have a good job and cool friends, but you just aren't sure how to flirt. The apps don't work for you. And sometimes women put you in the friend zone. It's frustrating. Hey, I struggled with dating too. As an introvert and a total nerd, I didn't just live in the friend zone. I owned real estate there. But I escaped. Using the dating philosophy of radical authenticity, which I've used to help thousands of men in 17 countries find love. It's what I wrote about in my best-selling book, Dating Sucks But You Don't. And radical authenticity is why psychology today called me the best dating coach in America.

And now I want to personally help you attract your dream girlfriend. So go to datingtransformation.com and book a free call with me. On our call, I'll tell you how my one-on-one coaching will help you find your dream girlfriend, and you'll be doing it by flirting with confidence and authenticity. No creepy pickup tricks needed. So go to datingtransformation.com, book a free call today, and let my personalized coaching help you get a great girlfriend. Okay, next question comes from Vikram. Vikram in New York City.

Vikram writes, hey, Connell, what actually makes a woman attracted to a man? Well, Vikram, different women are attracted. to different traits in different men. But here's one thing that virtually every woman wants, which is a confident man. Pretty much every woman wants confidence. Pretty much every quality woman wants that. And the fastest way to become confident is to become what I call radically authentic, which is simply about knowing your romantic worth to women and showing that worth as the

real you. So to me, dating is all about authenticity. That's where it starts with. And think about it. There's four billion men in the world, but there's only one you. It's only one you. You're unique. You're singular.

So when you finally start to realize how effing special you are, and you actually believe it, that's important, you have to believe it, women can just smell that confidence on you, like good cologne. But when you doubt yourself and you feel like, oh, man, I'm not enough. I'm not what women want. well they can smell that self-doubt like it's too much bad cologne too much drachar noir or too much x body spray just makes them go ew and this is why the whole fake pickup artist alpha male thing this is why guys like that come off as weird or creepy to women because they're masking

their insecurity beneath a pickup line or beneath a fake persona but when you know you're enough and you lean in to being your radically authentic self, you give women the two things that they crave, okay? Number one, authenticity. This makes you confident because you already know how to be you. Women love confident men. And number two, authenticity also creates trust in women. Women deal with so many men who are players, who are fake,

who have an agenda, who pretend to be somebody they're not. but when you tell the truth and you show that true self to women, you give them the trust that they want. So women want confident men and they need trustworthy men. I'll say that again. You're giving women what they both want and need. Women want a confident man. They need a trustworthy man.

And an authentic man gives them both truly authentic man as I define it. I remember the first time I really got this. And you can use the exact same tool yourself if you want to meet women, especially with approaching. I remember the first time I approached a woman in a truly authentic way. I was at a rooftop bar. She was wearing a silver dress. And I remember she looked like Jennifer Beals, my movie crush from Flash Dance. I started puberty watching Flash Dance in the early 80s.

So I saw this woman, and I'm like, oh, man, that's the kind of woman I've been dying to approach for years, but I wasn't doing it until very recently at that moment. Now, I felt nervous because I'm shy, but I really wanted to meet her. So I walked over and I just said to myself, before I said anything to her, I said, what is the most honest, truthful thing I could say to her that's not vulgar? So I walked over and I said, hi, I'm introverted and I'm shy, but you're my type and I had to meet you. I'm Connell. She was blown away, blown away. She said, hey, hi. Thank you for not using some weird line, she said.

She said, thank you for being normal. I'm Amy, and she was into me. And I was just being me. I felt so grounded. I felt so myself. I walked home that night, looked at her number in my phone. I just walked home thinking, damn, this is how I want to meet women. This is so simple.

it wasn't easy it was terrifying at first but it was simple so when you when you use rehearsed lines or you act like somebody you're not it's kind of like you're diluting your true self it's like you're taking the real core you but you're watering yourself down like a wine spritzer but when you're authentic it's like you're like a shot of top shelf 12 year scotch the good stuff the 12 year barrel age good stuff. Now, not every woman wants whiskey, but women who like your brand of quote unquote whiskey, she's going to catch a buzz off of you. So if you want a bonus tip, if you really want to dial this in, take authentic action. The next woman you see out, like at a social event, a bar, a lounge, think somewhere social. That's a good place to hit the ground running.

walk up to a woman and say exactly what you're thinking and feeling about her as long as it's g-rated don't be vulgar don't make it sexual again i could have walked up to that woman and said something sexual that would have been authentic it would have also been way too sexual too soon but i kept it g-rated and i just said hey you're my crush you look like my crush jennifer beals you're my type i had to meet you but i'm actually really nervous and that vulnerability that authenticity she loved it. Okay. Burning, here's the next burning question. Connell, women say I use too much tongue when going for the first kiss.

Any advice from Jeff in San Diego? Jeff, let me answer this as the movie lover I am. If first kisses were movies, aim for Sleepless in Seattle, not face off. Next question. Hey, Connell, how, oh, this comes from Anonymous, okay. Anonymous sent me this email. I mean, I know his name, but he said, please make this anonymous. I respect that.

He wrote, hey, Connell, how important are looks to women? Well, you might think that a man's dating success comes down to good looks, but that's not really the case. Looks don't really matter all that much to women. Good looks are like jacuzzis in dating. They're nice to have, but they're way overrated. So, yeah, if you have chiseled Liam Hemsworthian features, good for you. But take it from me, the guy who's dated some pretty incredibly beautiful women, even though I look like Ron Weasley's brother,

you don't need to be great looking to have a great dating life. Looks don't really matter unless you make them matter. But as men, we get so hung up on this myth. I know I did back in the day I think it happens because as men we tend to value physical beauty in women because we're very visual if not shallow I'm pretty damn shallow I'm a very shallow I am the kitty pool shallow right I love a pretty face and as men we tend to project onto women the way we see women and we think oh well as men we're pretty visual we love a pretty face an attractive figure.

So we project our preferences on to women and assume that they see us the same way. But they don't. They really don't. So you might want to date a gorgeous woman who's got model caliber looks. And if you do, then you probably assume the reverse is true,

that women want to date Hollywood handsome looking guys. And I'm not saying women don't want a handsome guy. I'm just saying it's not nearly as important to women. looks are not nearly as important to women as they are to us that's what i'm saying so i'm not saying looks are irrelevant i'm saying they just don't matter nearly as much here's some proof of that here's a fun fact there's a health there's a health app called clue clue is a health app that uh six or seven years ago they surveyed 64 000 women and asked women what traits they most want and want in a male partner and here are the top five traits these are the top five traits these are the top five

things women want in a male partner according to a survey of 64,000 women. So this is very scientifically sound. Number one, kindness. Number two, intelligence. Number three, education. Number four, supportiveness. Number five, confidence. Good looks did not even crack the top 10. So if you're not Hollywood handsome, don't sweat it. Feature what else you can bring to the table. Maybe it's your intelligence, your wit, your heart, your get good at flirting, which is what I do, what I teach, I should say. And your sense of humor, basically lean into other things that you bring to the table if it's not your looks. Don't sweat it. Bottom line is good looks. Women want swagger, confidence, a man with that steely self-worth. And when you believe

in your worth to women, you're going to come off as sexy as Brad Pitt. even if you look like Brad Garrett. All right. And then one more question. This is a classic question. I read this one a few months ago, but it's back by popular demand. Somebody wanted to hear it again. This comes from a guy I will call John in Dallas.

This is not his real name, but this is a real question. I kid you not. Hey, Connell, I'm 5'4, and women always reject me, both on the apps and off. So, I'm considering a painful surgery. in which my legs will be broken in multiple places and lengthened to make me 5 foot 7. Gaining about 3 inches, John says. It costs about 100K. Should I do it?

Whoa. Okay, 100K to have your legs broken. John, I know a guy down at the docks, Nikki the Nostril, he'll do it for way less. A bargain. like 100 bucks 100 bucks anyway i feel your frustration john or any guy who's on the shorter side so i say this with utmost respect are you effing bonkers do not do this do not have your legs broken and lengthened let me get this straight you want to pay a hundred grand have both of your legs broken in multiple places the bones are going to be slowly pulled apart screws are going to

be inserted to keep the bone apart so the bone can regrow in the broken places and you're going to spend months in a painful recovery to maybe gain two or three inches so we're talking wheelchairs crutches pain physical therapy you're going to miss work and you could have re-breaks you could be shooting baskets a year from now and you come down after a free throw and then crunch re-break your leg? All of that for height? Don't do it. Don't do it. Let me ask you, John, quote-unquote, John, are you sure that gaining just a few inches of height's going to fix your love life? Are you sure a few inches taller is going to make things okay because it won't? High is not some magic pill. I'm six foot two. I'm pretty much the perfect height. I'm not too tall. I'm certainly not too short.

And I had epic dating struggles back in the day before I figured out my love life and how men can connect with wonderful women. So your height is not the problem, not the main problem. The real issue, John, is how your height lowers your confidence. And by the way, dear listener, I am not only talking to John. I'm talking to you as well right now. If you are under 510, okay? If you're in your head about your height, listen up.

the real issue is how your height or your perceived lack of height lowers your confidence your your very belief your perception about your height that is hurting you so much more than your actual height look different women go for different things as I said earlier in the episode every woman pretty much every woman wants a man with self-confidence so the way you feel about your height is hurting your most attractive trait, your confidence. And it's a lot easier to strengthen your confidence than to lengthen your legs. By the way, lean back up here. This whole idea that women only want tall men.

Big fucking myth. Bullshit. The truth is, women want men. A woman wants a man who can make her feel safe, feminine, protected. now some women feel that way if a guy is tall that helps but the thing is a shorter man can give a woman those same feelings just in different ways he can get strong at the gym he can get ripped he can develop charismatic personality he can get really certain and strong and confident in who he is which is what i teach no matter how tall you are you can get really good of flirting there's lots

of ways to give women that sense of certainty that they are with a quote unquote man take it from a six foot two guy who sucked with women for 35 years 35 years i sucked with women if height was everything i would not have struggled so badly but i was so low in confidence it didn't matter there's another little myth for you buddy you think that women want only women only want tall guys no Now, sure. Is tallness, is height a nice bonus for a lot of women? Sure. Absolutely. But most women simply want a guy who isn't shorter than she is. There's not some magical rule in dating where if you're under six feet, women aren't into you. The truth is women, the women who do have a height preference, it's really just, I don't. They feel like I just don't want a guy who's shorter than me. Many women feel that way. So if you're 5'4, John, guess what? you have tens of millions of potential dating options in the USA anyway because the average height of an American woman is five foot four. You are five foot four, which means that roughly half of the adult women are going to be at or lower than your height, which means they're in your

dating pool because women really only care about. I want a guy who's not shorter than me, not that he has to be six feet. So what's hurting your love life isn't your height. it's how your height hurts your confidence and how that makes you insecure that's what turns women off so what do women actually want they want a confident man who knows his worth and who makes her feel special and that's true of women whether the guy is six foot four or four foot six so you don't need towering height you need towering confidence so my advice is build your confidence up from the core, from your very core, not from breaking your legs and having longer legs. That's not going to be a magic bullet. I tell every one of my clients, you are enough. You are enough. And in your case,

John, I mean that literally there is enough of you. You don't need three more inches to become worthy of love. What you need is to see how worthy you already are and begin to believe that. All right. Thank you so much for listening. Until next time, later.