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How to Flirt with Women: the Wrong Way (DON’T do this) and the Right Way!

Featuring NYC Dating Coach Connell Barrett
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In this episode, learn how to flirt with women. Learn what to do and what not to do.

Chances are, you struggle with how to talk to women. You’re just not sure the right way to flirt or what to say, and you get stuck in your head. Or perhaps you come across as boring or not charismatic. And women just don’t seem to feel romantic sparks with you. It’s frustrating!

You’re in luck. In this episode of the Dating Transformation podcast, dating coach Connell Barrett shares the two BIGGEST mistakes that men make when trying to flirt with women. (Make sure you’re not doing them!) He also shares the RIGHT way to flirt with women, and how to do it with natural confidence and authenticity, to create real connections.



"When you flirt with true authenticity, you're giving women the gift that they most want: the real, best you!"

-Connell Barrett

Featured in the episode

Connell Barrett

Founder and Executive Coach of Dating Transformation




00:00 - Introduction

01:48 - The Right and Wrong Ways to Communicate with Women

03:02 - Waiter Persona: Navigating Over-the-Top Communication

06:43 - The Power of Being Present and Genuine

09:24 - Avoiding Supplicating Pitfalls: Mastering Dating Channels

13:20 - Authentic Attraction: Beyond Supplication and Cockiness

17:48 - Genuine Connection over Performative Acts

19:14 - The Power of Vulnerability: Connecting Authentically

21:12 - Real Talk: Forging Genuine Bonds in Dating

23:10 - Building Trust: Authenticity and Shit Detectors

24:38 - Breaking Barriers: Honesty and Connection in Dating

26:19 - Story Swapping: Crafting Memorable Conversations

29:47 - Outro

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Yeah. D don't take the red pill. Don't don't swallow that pill. I'd rather swallow arsenic than the red pill.


Welcome to the Dating Transformation Podcast. Here's your host, Dating Coach, Connell Barrett.


Connell Barrett:


Alright. Welcome back to the dating transformation podcast. I'm your host, Connell Barrett. I'm the dating coach for men. I help guys like you gain confidence, learn to flirt and attract an incredible girlfriend, all by being radically authentic, putting that real authentic self out there to make genuine connections with women as opposed to picking up artist moves. And If you're a guy who struggles with what to say and how to say it to women, then you're in the right place today because I wanna talk to you about The three main ways men talk to women, the wrong way, the really wrong way, and then the right way. And I know you're gonna want the right way. So at the end of the pot, I'm gonna talk about the right way to do it. but bottom line is what probably the biggest question I or the question I hear most often is, hey. How do you talk to girls? What do you say? How do you flirt, struggling with what to say, and how to talk to women? It really drives a lot of guys crazy on dates. It makes it hard to approach when you don't know what to say. It gets you stuck in your head on dates. And, basically, it makes it really tough to create those romantic sparks we want. So today, we're gonna talk about helping you fix that. So before we do that, let me tell you about the three different, let's call them, communication channels that men most often fall into. Before I get to those three, let me share a story with you to illustrate it. Before I became a dating coach, in my previous life, I worked as a restaurant critic. I was able to go out. I worked for a magazine. I was a writer and editor at the time. I worked for a New York City magazine, and I had a really cool job. I got to go out and do restaurant reviews. And I remember a certain week, years ago, when I was out reviewing restaurants here in New York City, I went to three different restaurants over the course of a week, and I had three very different experiences with the server who was serving my table. So the 1st restaurant I went to was a fancy fine dining establishment. And I remember the waiter We had the main waiter that my friend and I had. He was very supplicating to our table. He apologized for interrupting when he came over to the table. He treated my dinner companion and I, like, we were you know, kings. We were gods. And don't get me wrong. That can feel kind of good to an extent at a fancy restaurant because part of the reason you go to a restaurant is to be pampered a little bit to get a look to get spoiled a little bit. That said, there was something there was something about it that just left left me feeling a little bit like, ew. It it was it was a little bit it was fake for one, but also it just felt like Our waiter was putting us on a pedestal. Is there anything else I can get for your table? If you need me, I'm just a moment away, It just felt very, artificial and basically, supplicating but kissing for lack of a better term. And so that was the 1st restaurant, the fine dining place. Then a few nights later, I went to a steakhouse here in New York City, a famous one called Peter Luger. And, Peter Luger had a very opposite different kind of server, another waiter, a man, came over. And Peter Luger, the the waiter we had that night, he was talking at our table the whole time. He was basically it was almost like he was doing a monologue. reciting some, like, shtick, almost like lines he had rehearsed about the history of Peter Luger, why it was the greatest restaurant. I also remember him, like, sort of trying hard to, like, tease us and, and, like, make fun of us if we ordered something that wasn't the right thing to order on the menu, and that was also off putting. So it was like he was doing material. He was talking to us , putting on this persona of, like, oh, hey. I'm the cool cocky waiter who doesn't give that much shit. And I'll I'll fuck with you. And that was also a little bit off putting. Well, it didn't, it didn't ruin the meal. It's an amazing meal, but I just remember thinking that's just strange behavior.




I'm gonna read your mind. Ready? I'll bet that you would love to confidently approach women. Get great matches on the dating apps, flirt with charm, and attract your dream girlfriend. Right? But fear keeps you from approaching. You're not sure how to flirt. You struggle on the apps. and desirable women just don't seem into you. Well, I have great news. Dating Coach, Connell Barrett, can help. He's guided thousands of men like you to more confidence and help them attract their dream girlfriends. So book a free strategy called Today To see if Connell's coaching is right for you. On your call, Connell or a team member will give you personalized advice to help you have more confidence More dates and more fun. Oh, and you'll be dating women as your best self. A charming gentleman. That's because Connell does not teach creepy pickup artistry. He unlocks your most confident self, so you can make authentic, romantic connections. Your next steps, book your free call today and grab a time that works for you. Then you'll be on your way to more confidence, better results, and attracting bright, beautiful women. owe. So, you know, soon, Connell will stop taking on new clients. So book a call today while you still can. Go to and transform your love life. Bye.




And then for the third restaurant, My date and I went to another fine dining restaurant, but the 1st one was more like a white tablecloth, fancy see crystal glasses kind of place. This third restaurant, it's a restaurant called Gramercy Tavern. They are not a sponsor. I'm just That's where it was. And the cool thing about Gramercy Tavern, it's very casual. It's fine dining, but it's very casual. And what I remember about our server that night who who's a woman. I remember how genuine and chill she was. She was great at serving our table, but she did not talk to us like we were above her. She did not have any canned, planned material. As far as I could tell, she had no agenda. She had no script she was reading. She was just really present. and genuine. I remember a couple details about her, even though this was years ago, But I remember some details about her. She had a really cool, unusual clock tattoo on her right arm. I asked her, "What was it about the clock tattoo? Why did you get that? And she told the story about going to London when she was a little girl with her parents and the clock tattoo reminded her of her mom and her grandmother. And every time she came over to my dates, my table, my date and my table, our server was just such a genuine real connection. and she gave us a great experience. She basically gave us what she wanted to get back in a sense as she was being genuine. She was being real. Yes. She served us. But at no point was she being fake? She was just really real. She was just really genuine and real. And I left that restaurant feeling like, you know what? All three meals were great in terms of how the food tasted, but you know, the experience that we love the most was Gramercy Tavern, and that server. I forgot her name. It's been so long. We made a real connection. We felt like we were really connecting to that waitress. She even would come over and she wouldn't hover, but she would just chat with us and shoot the shit while also being an incredible server. And so those are the three categories of servers I had. The 1st one was the supplicant. The second server was, I don't know, cocky, cocky script reading performance. And the third was so genuine and real and natural. So you might know where I'm going with this. Those are the three most common channels that a single guy like you can get onto. Typically, most men when you go on a 1st date or approach a woman, or you're talking to a really cute girl at a party, it's really easy to fall into the 1st two channels to be that supplicating guy who puts the woman on a pedestal And if you do that, you come across very much like you're beneath her. You're serving her. It's a bit of a persona. You're not offering anything. You're just basically trying to make her happy and not sharing any glimpse of who you are. So let's call that the supplicant. Right? Have you ever been on a date? Or have you ever been talking to a woman, at a party or at a social event and you find her attractive. And you're just not sure how to behave, how to talk, what to say. So you just basically find yourself asking her questions, interview mode, And you are thinking, oh, gosh. I hope she likes me. You lean in a little too much, or you lean in a lot. You're very eager to please. That's what it is. Eager to please. Just like a supplicating waiter, you're like a supplicating dater. Oh, I think I just came up with the title of my next book. the sublocating data. So, I think a majority of men fall into this category. in terms of how they talk to women. So if you've ever been on a date and you just found yourself or talking to a cute girl and you just find yourself asking questions, putting the onus on her to fill the conversation, or wanting or agreeing with everything she says, finding everything she says, fascinating, even when it might not be always fascinating. That's supplicating data, much like the supplicating waiter kind of gave me the creeps at that fine dining establishment. I'm actually just thinking back, actually to one of my very 1st clients. Again, Jeffery, years and years ago, one of my very 1st clients, I took him out to approach girls, at a bookstore here in New York City. One of the things I do with my clients here in New York is to go out with me as their wingman. And Jeffrey was walking up to women, and he sounded at the time I called at the concierge, but I think if it's more now, it's more like that supplicating server. He was walking up to women saying, well, hello, lady, my lady. And how are you this evening? Are you finding any good books you'd like to read? I mean, he literally sounded like that. I'm not exaggerating. And that's not how Jeffrey talks. So he was putting on this persona, putting on this, please like me, give me your validation, you're above me, And that is a terrible vibe to put out there because it sends all the wrong signals to women. It sends signals that you are eager. You want her to like you a lot, which suggests you don't have many other options. And even if you don't have other options, which I totally feel that pain, you don't wanna come across that way. You wanna come across as if you have an abundance of options. So that 1st category, the supplement is what you wanna be aware of. Are you doing that? Are you over eager? Are you asking her all the questions? Are you thinking, please like me, please like me, please like me, please like me, Are you, basically, are you elevating her above her? Are you putting her on a pedestal? That does not work. Now the second category is also bad. I think it's worse, actually. So the 1st one is bad. The second one is really bad, the restaurant example is the cocky performance waiter who's, like, talking at you, trying to pretend like you don't care that much. Well, you know who you know where this comes from. This comes from YouTube dating experts who I will not name, but they fucking suck. This comes from the Red Pill losers, the so-called dating experts, almost exclusively men. who say you've gotta be an alpha male. You gotta be high value. You've gotta have a cool car. You gotta talk down to women. you've gotta be toxic. You gotta show her who's boss. That toxic alpha male complete fucking bullshit. That absolutely sucks. Now I know that that's not who you are at your core if you're listening to my podcast. but maybe you've tried that persona on. Or if you haven't tried it on, you've probably seen YouTube channels or other, dating experts, maybe podcasts where they say, yeah, be a bad boy, be an alpha male, take the red pill, if you've ever if you've ever gotten stuck in a quicksand, that is Reddit's red pill page. you know what this is about. And guess what? That's even worse than the 1st one because it's very agenda driven. It's you you're putting on this really this really fake false mask trying to be some kind of asshole, some kind of douchebag talking at women. And I know this from personal experience because when I was out there working on my dating life, I hired at least 15 different coaches. I work with coaches who were great, coaches who sucked, coaches who were somewhere in the middle. And I even had a coach who basically said, oh, yeah, Connell, do this for a month. go out and be an asshole. Go out and be an alpha male. Basically, do the toxic male thing. And I tried it for about 10 or 11 days. and it felt awful. It wasn't me. I felt like I was wearing an ill fitting suit. a really garish, ugly suit with chains and a fake hairy chest, and I don't know, a peacocking hat. It just felt so fake and weird. So that second zone also doesn't work.



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So you probably haven't used this very much, but if you see YouTube channels where they talk about being a man, being alpha male, women want a tribal leader, show her who's boss, red pill, please run screaming from that page. That's not gonna help you. It's not that's not what works. But that's also a mistake that men fall into. I fell into it myself. I tried it for about 10, 11 days. And then I finally said, you know what? This feels awful. I was saying really polarizing shocking things to get reactions. It didn't work. It was fake. It actually led to having a woman pour a glass of ice water down my shirt because I was being such a dick. and it was a well deserved glass of ice water. She absolutely absolutely absolutely deserved to pour down my shirt. so don't fall into that second class. Don't be that fake alpha male guy who's telling women who's boss. That's not what women want. And then we get to what does work, right, that server I had. She was just really real, genuine, listening, present. She was giving to our table what we wanted. but also she was letting us give back to her. She was letting us talk about listening to her as we were listening to her. She was listening to us. She was just putting her real personality out on the line, and that's what this that's really what this is about. If you wanna get good at knowing what to say, and knowing how to talk to girls. Then the first thing you have to do is drop the applicant. You're better than me. over eager persona, you have to definitely resist and reject the toxic alpha pickup artist BS. What you need to do is take the mask off and just be really authentic, genuine, what I call radical authenticity. showing women that true, real best self. And I was thinking, what does that mean? I mean, I know what it means. I wrote a whole book about it, but in terms of how to talk to girls in an authentic way, what does that mean? I think Here's a good way to think about it. I hope I hope you'll agree. I think this is a good way to think about it. Being radically authentic or seeking to make an authentic connection. It's about first giving to that woman. what you want to get back from her. It's about first giving to her what you want. So I hope what you want from her is some clear romantic interest. Great. Who wouldn't? So first, give her that from you in a vulnerable way. Empathetic, not vulgar, but vulnerable. So you first wanna show her some of that genuine interest before she gives you her real most vulnerable, emotional, personal side, you first have to give it to her. You've gotta give it to her first. as the man, you're gonna have to go first probably. So you wanna be the first one to say something flirtatious. You want to be the first one. to take a romantic risk and give her a compliment and let her know something about her that you really like. That vulnerability is part of being authentic because you would love that back from her. Right? Wouldn't you love a really smart, bright, beautiful woman to say to you, hey. You're really handsome, and you're really fun to talk to. I like you. Of course, you would. that'll change your life. That'll make your year. Well, then what you gotta do is go first. you've gotta give her that first. You know, to get, you've got to give. And the most valuable thing you can give is your true, real authentic, genuine vulnerable self. That's what that waitress was doing. years ago. Oh, gosh. I wish I could remember her name. She was just so vulnerable, cracking jokes, talking about her tattoo, telling stories about London. And then asking us about our stories. She was letting my date and I open up, and we were talking about the restaurant business. I think she has. I think she had children, and we talked about her kids. It was just such a real connection. And that's really what this is about. Authenticity, putting that real authentic self out there, is what leads to connection because a woman needs to trust you before she'll really open up and connect with you romantically and being real being authentic, being vulnerable, gives her a clear signal that you are a trustworthy man. because women have great shit detectors. I think we all have good shit detectors. And my shit detector was going off with the supplementing waiter, my shit detector was going off with the alpha male weird, cool, cocky funny waiter. And then as soon as I was being served by this authentic, genuine, chill, cool, quirky, kinda weird, but awesomely weird waitress, so We totally hit it off because I was seeing the real her. I knew I could trust her. And similarly, when you go on dates, you wanna show women that they can trust you. and that also so when you're truly authentic, you're not just saying, hey. I'm trustworthy, you're also saying, hey. I'm confident enough to show you my real self. And that's a really powerful and very often attractive thing to women is like, oh, this guy is just not afraid to be his real self. So a couple practical tips here for how to do this, how to talk to women in that radically authentic way. Here's a great rule you can follow. Something my very first coach ever said to me. The rule is what I'm thinking and feeling is what I'm saying and doing. Being really honest and real and raw with a woman. So you say you walk into the 1st date and you're nervous. You're kinda in your head a little bit. Maybe there's some sweat on your forehead. totally fine couple minutes into the date to say, oh, hey. By the way, I'm actually feeling butterflies right now. You're I'm I've been looking forward to meeting you all day. You're really cute, and I'm kinda hoping this goes well. So I'm feeling a little bit nervous. That alignment with what you're feeling inside the vulnerability and expressing it, that is so rare to women, and it's so disarming. and it will also relax you. So you can say those kinds of vulnerable honest things. That's one way for women. Another way to talk to women through the lens of being authentic and trying to make a genuine connection is to share your honest true opinions and feelings. If you agree with her, if you totally see things the same way, you can totally agree with her. Why not? Absolutely. It's great to see. It's great to have commonalities, but maybe you don't agree with some of the things she says. that supplicating guy is gonna agree with everything she says, and she's gonna smell a kiss ass. If you just kind of basically grow the stones or summon the stones to say, oh, actually, you know what? I disagree. I think X Y Z is a better movie. Or oh, no. I really really hated that album. What? Do you like that album? Oh my gosh. You have terrible taste in music. I don't know if I can date you. you'll grow more comfortable when you're when you start being authentic and honest with a woman on a date. And the more comfortable you get, the more confident you get, the more confident you get, the easier it is to talk, to flirt, to know what to say. and then one final tip about what to say and how to say it, from that lens of authenticity is I want you to think about sharing a true oh, here's a good way to do it. Come to a date or a conversation, be ready to share a true, honest, ideally vulnerable story from your past. That will be very compelling to her because, a, everybody loves a good story. b, you're being real and vulnerable, and that's really compelling. C, you're making yourself literally more charismatic at the moment. because stories get people reacting to us. And when you're getting somebody reacting to your energy, your authentic real energy, that makes you charismatic to them because they're the audience and you're on stage in a sense. So you become sort of that. cooler, attractive guy who's sharing, bringing her into your world. Also, the great thing about storytelling, having a really good personal anecdote from your life, from your past, is once you tell yours, that's gonna give her the green light to then have her open up about stories from her past. And you know what a really great date or flirty conversation can be. It can be two people swapping increasingly fun, funny, vulnerable life stories. It can just be a bunch of quick anecdotes and stories back and forth with some light playful chat in between. and because you're being your true selves, you're hitting it off. And because you're going first, because you're first giving her What she wants to give you, you're making a genuine connection because you're doing it from a place of contribution. You're giving in order to get it because remember, the supplement is trying so hard to get her to like him. That's agenda driven. It's also manipulative with a lowercase m. The alpha male pickup guy who recites all this bullshit, toxic nonsense, and canned lines, He's being manipulative with a capital m because he's doing it as a completely false persona and purely for his outcome. So that's manipulative, and that's also selfish. But when you're in that 3rd authentic place, you're giving first what you wanna get. And if you don't get it, that's okay. Maybe she won't give it back, and that's fine. At least you tried. But Take it from me. Women love a guy who first gives to them. and that compels them to wanna give back, especially when it's coming from that authentic good intentions place. Alright. Hope that makes all the sense. Thank you so much as always for listening. And don't forget, your future girlfriend, She's out there. And she may not have met you yet, but she already likes you. She just has to meet the real authentic you. Alright. I'll see you next time.




Thank you for listening to the dating transformation podcast. For lots of free tips, videos, and other goodies, Go to dating See you next time.


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Dating Tranformation with Connell Barrett

Welcome to the Dating Transformation podcast. I'm coach Connell Barrett, and I help men build confidence + connect with women by being their own authentic selves.

dating sucks but you don't #1 Amazon bestseller

Get this Book & Attract Your Dream Girlfriend


NYC Dating Coach Connell Barrett

106 W 32nd St, New York, NY 10001

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