How to Get a Girlfriend with Connell Barrett - My Flirting Hall of Shame: 7 Times I Screwed Up Royally with Women (Learn from My F-ups!)

Episode Date: June 11, 2026

You can’t get great at flirting without making mistakes, as dating coach Connell Barrett learned the hard way. In this candid and hilarious episode, Connell shares 7 huge flirting mistakes he made��including the time a woman poured a pitcher of ice-water down his shirt. He also shares 7 lessons that helped him crack the code on male-female connection.NOT SURE HOW TO APPROACH BEAUTIFUL WOMEN? BOOK A FREE CONSULTATION WITH CONNELL: DatingTransformation.comGET A FREE COPY OF CONNELL’S BESTSELLING BOOK, “DATING SUCKS BUT YOU DON’T”: Email: [e-mail] (Write “Free Book” in Subject Line)

There's going to be a moment when you have to play to win. You have to take a chance. You can't succeed in dating and making connections happen unless you take some chances. Welcome back to the How to Get a Girlfriend Podcast. I'm your host, dating coach, Connell Barrett. I'm here to help you flirt with confidence, know what to say, get a great girlfriend, and do it all by being authentic, what I call radically authentic. No sketchy pickup artist moves needed here.

It's about being your best real self because mom was right. women like you for you. Today I'm going to share with you my flirting hall of shame. Seven mistakes that made dating so much harder than it had to be. Seven flirting mistakes. I wish I could tell you that I became so good at dating and so good with women because I'm some naturally charismatic, confident dude. It's quite the opposite.

I came from such a low place. I was largely dateless through my mid-30s. And the one woman who I met and connected with before then, she and I decided to get married. I settled. She settled. And then she dumped me nine weeks later. So I came from a place of struggling with dating. I had to learn how to get first just competent with women and then eventually confident and

really good at dating and flirting. I had to learn. And the way I learned was I made a lot of mistakes. So many mistakes. so many mistakes, especially with flirting and what to say and how to say it. The right and wrong things to say on dates, the right and wrong things to say when you approach, I made every mistake in the book and created some new mistakes as well. So today I want to share with you my flirting hall of shame. Seven mistakes that made flirting and dating so much harder for me that it

needed to be. And my hope with today's episode is that I can help you cut down on the amount of time It'll take you to have that next great date to find that woman who's going to change your life, who you'll be able to share your life with. So let me save you some years and months starting right now. Let's get to my dating and flirting hall of shame. Story number one, I call this be a dick. Be a dick. Let me tell you about the time a woman dumped a pitcher of ice water down my shirt because I was acting like such a dick, such an asshole. At the time I was working with my coaches who were mentoring me, and I had great coaches, I had bad

coaches. And I had one coach, a pickup artist dude, who said, Conall, you're too nice. Women don't want nice. They want bad boys. So go be a dick. Be a dick for like a month. Go out, approach women, just be a dick. And I didn't like the advice, but I tried it.

And I went out for a few nights and I put on this mask of sorts, acting like a dick, an alpha male and I would say obnoxious things to women. I remember telling some women on the dance floor, no dancing over here, no dancing allowed. And they looked at me like it was an alien. And another group of women I approached one night at a bar here in New York City. And I was really leaning into this cocky, jerky exterior that I thought, hey, I guess that's what you need to do to impress and attract women, right? And I was being such a polarizing asshole. that this woman I was talking to, her friend went and got a picture of ice water. And in the middle of my nagging, teasing self, a conversation with her friend, she poured a

picture of ice water down my back. And deservedly so. I deserved it. And that was the moment I said, okay, I've got to change things. I didn't like the way I felt, not just because I had ice water down my back, but because I just felt like I wasn't being me. I wasn't. being real. And so the big lesson for you here is I want you to ignore any so-called dating experts. It's always men, by the way, who say, be an asshole, be a jerk, be an alpha male. Fuck that. Don't do that. Be vulnerable. Be real. Be you. Speak your honest thoughts. If I was walking up to those women and being really honest and genuine, I would have said, hey, ladies, I have to be honest. I'm intimidated to meet you. You're also beautiful, but I wanted to come over and say,

say hi. And it was actually that kind of authentic approach that's that worked so much better than the fake be a dick persona I was putting out there. So don't be some fake alpha male. Don't be a dick. Be the true best you. A woman who likes you is going to love that version of you. Okay. Let's go to the next story. This one is I call this story playing not to lose as opposed to playing to win. So let me tell you about the time I screwed things up with Brandy because I was so afraid to go for the first kiss. Brandy is a woman I met on a dating app. We had a couple dates. We were at the end of our second date and I had not gone for a kiss yet. And we're sitting in a park on a park bench and she was giving me signals. There'd been some nice mutual touching,

mainly from her, touching my knee, touching my shoulder, twirling her hair. She was giving me all of these signals. And at the time, I just felt like, no, don't be creepy. Take it slow. Don't say or do anything that might come off as creepy or weird. And it's a Thursday night in this Brooklyn Park. It's romantic. It's summer. Things are going really well. There was a nice, long, romantically tense moment when we looked at each other's eyes and I could just see it's almost like there were words in her eyes that said kiss me now and I didn't do it. I was afraid and I just kept talking to yak, yak, yak. And I could see her disappointment.

A few minutes later we start walking away or she gets up and says, well, I'm going to go home now. And I knew what I had done. I knew I had screwed up. And I actually walked up alongside her and I tried to kiss her. And she pulled back and said, no, sorry, Connell, you had your chance back there. I've lost interest. Harsh feedback, but honest feedback. And Brandy was right.

And the big lesson that I took away from that night was stop playing to avoid losing. Stop trying to avoid losing. Don't play not to lose. play to win. If you're on a first or a second, in this case, date with a woman, then there's going to be a moment when you have to play to win. You have to take a chance. You can't succeed in dating and making connections happen unless you take some chances. And that was a valuable lesson. I never connected with Brandy, but thank you Brandy for teaching me an amazingly invaluable lesson about playing to win instead of playing not to lose. Okay, let me take a little pause here to

say, as you might know, if you listen, I'm a dating coach. I do one-on-one personalized coaching with men. I can coach men anywhere all over the world. I also do in-person coaching with men here in New York City who want to go out and do in-person approaching training with me. So if you're a guy who's interested in learning about how to talk to women or getting more confident and comfortable so that you can approach, which now is an amazing time to do that, What you can do is go to my website, datingtransformation.com, and you can book a free call with me there. I also am very active on Instagram and TikTok. And if you're on Instagram or TikTok, you can find me at dating transformation on Instagram.

And I believe I'm Connell Barrett on TikTok. And you can shoot me a DM if you have any questions about how my coaching works. Easiest thing, though, is to go to my website, datingtransformation.com. Okay. let's go to story number three. I don't have a catchy name for this, but let's call this, let's call this, you're sexy. That's the name of this story. And the story goes back to, I had already begun to approach women, but I want to tell you about the girl who taught me the truth about how to tell a woman she's sexy and do it in a non-

creepy way. I approached her at a cool venue in New York City called Beauty Bar. And I approached her. She was with a group of friends. And I will call her Amanda. Amanda and I are now sitting up at the bar. She moves away from her friends. She's really enjoying talking to me. I take her on what's called an instant date. An instant date is when you go from approaching a woman to sitting at the bar or wherever where you are and having a one-on-one conversation, basically an instant first date, even though I just met her 10 minutes earlier. So Amanda and I are talking, and she, I was dying to tell her how sexy I found her, but I was afraid. I thought that'd be creepy. You can't tell a woman. She's sexy, right? That makes it all about her body. Isn't that wrong? Isn't that weird? And I looked at her

and she told me that she had recently backpacked through Europe. And I said, you know what's really sexy about people who do that? It's so sexy and attractive when somebody just decides to go and travel on their own. I think that's so cool, so sexy. And I remember Amanda, her eyes got really big, and she leaned toward me and said, So, Connell, are you telling me that I'm sexy?

She was coaching me in real time. And I said, yes, yes, I'm telling you that you are. And she said, good, good job. And then she just straight up said, by the way, you can just tell us we're sexy. It's okay. We like it. In that moment, Amanda wasn't just talking to me. I feel like she was talking to all single men.

And I really appreciated that. And it was a big shift for me in that moment of realizing, you know what, it's not creepy or weird. to tell the woman she's sexy, you know, assuming you've gotten to know each other a little bit, which she and I had at that point. And that's what I want you to take away. If you're on a first date or a first date setting, if you find something cool, sexy, charming about her, tell her. And feel free to use the word sexy. It's scary. It's scary to look a woman in the eyes and say, you're sexy, but Amanda really liked it. Not only did she like it, she coached me into saying it to her. So thank you for doing that, Amanda.

All right, story number four. I call this dancing monkey mode. Here's the story of the approach I did that I thought went amazing, but boy, that I screwed up by making women laugh the wrong way. I was in Oslo, Norway, taking an approaching dating course from one of my coaches way back in the day long before I became a dating coach. And I felt like every woman says they like funny, right? So I'll just crack jokes. I'll be funny. And I approached a couple of women. And my coach, my coach, by the way, a guy named Alex was standing nearby. He was watching, being a good coach.

And he watched me approach these women. And I walked up and I started cracking jokes. I don't remember what the jokes were. It's been many years. years, but I had them laughing. I had them laughing, giggling. That sounds really good, right? And after two or three minutes of joke, joke, joke, funny, funny, then I take out my phone and I say, hey, by the way, I'm visiting here for the whole weekend. We should get together. What's your numbers? And one of them said, oh, no, thanks. We're not interested. But you're very entertaining. Have a good day. And they walked away. Incredibly. polite. It was one of the most polite rejections I'd ever experienced in that moment. And I was

really befuddled in the moment. I thought, wait, women like funny guys. I was funny. I made them laugh. Why don't they like me? And Alex, God bless him, was watching the interaction and said, well, you were funny, but you weren't basically attractive. You were like a stand-up comedian. He said you're basically in dancing monkey mode. Avoid dancing monkey mode. Dancing monkey mode is you will say and do whatever it takes to make a girl laugh, but that doesn't create romantic sparks. That doesn't create a kind of a flirtatious spark that we want in women. Here's what does or what can create that. There's a way to use humor in a way that can create romance and sparks with a woman. I found one of my favorite techniques for doing that is I call it faux arrogance, fake arrogance,

meaning I will say something to pretend that she is treating me like a sex object. So for example, on a first date, I have said this a few times. Feel free to steal this. A woman was looking down at my shirt, just checking out my outfit. And I would say, excuse me, my eyes are up here. please, I'm not a piece of meat. And she'll laugh. And I realized that's the right way to use humor in a dating setting that's flirtatious and that can create those romantic sparks.

As opposed to just trying to be a funny, joke-cracking dancing monkey. So that was a really valuable lesson I learned in Oslo, Norway. But man, there are plenty of other things I screwed up along the way, which brings us to, oh gosh, This is so painful. Story number five, fawning over Georgia. I want to tell you about Georgia. The Blake lively lookalike I used to work with at a magazine, but I screwed it up by fawning all over her and totally ruining my chances with her.

So I used to work at men's and women's magazines back in my journalism days long before I became a dating coach. And a woman named Georgia, I was absolutely. infatuated by her. She's beautiful, charming, funny, just dynamite, a total 10 inside and out as a person. And somehow I got her to agree to go on a date with me. I still don't know how I did it. Someone is beautiful and wonderful as she having, basically seeing something in me back then, still, still in a way surprises me. So we go on a first date. And the flirting mistake I made is I fawned. I could not shut up. I didn't want to get friend zoned.

So I said, don't get friends zoned, Connell. Come up with something. And so I said, let me just flirt with her and really put it out there. And I said, I said, your eyes are stunning. Your eyes are gorgeous. And a few minutes later, I said, by the way, your smile is dazzling. And later that night after we said goodbye, I texted her. This was amazing.

I'm so glad we got to hang out tonight. I can't wait to see you again. And there were three or four other comments that are lost to time because this was many years ago. But I would say I gave her five or six really intense your amazing compliments. Now, there's nothing wrong with complimenting a woman, but there's a fine line between fawning and flirting. And fawning is when you go, oh, so over the

top in your flirtatious compliments to a woman that you make her feel like she's a movie star and you're the autograph seeker. And I'm sure that's what Georgia was feeling. And valuable lesson. She ended up dating a different guy who worked in my department. That was tough to deal with because here's this guy dating Georgia. But it was a really valuable lesson. So the lesson to take away, it's not don't flirt, it's don't fawn. When you compliment a woman, and here's a good quick fix for making your compliments land in a non-fawning way, compliment a woman and let her know what you like about her, but make it a trait.

Don't make it your eyes are dazzling, your smile. I've been thinking about your smile all day. Avoid that kind of compliment. Think something, like if I can go back in time, I would say, Georgia, you know what's fantastic about you, what's really attractive and charming. You're so intelligent. You're so smart. You're so good at what you do. I find that really attractive, really appealing, really sexy, really charming. And that is not fawning. That's flirting because you're showing your romantic interest, but you're not lowering her to below her status. So a valuable

lesson that I learned, but I first had to screw it up to learn it. Okay. Continuing the cavalcade of Connell screwing stuff up. I made so many mistakes over the years. So many flirting mistakes, so many approaching mistakes. What should we move to next? Here's a good story. I call this one too cocky Connell. How about that? The two cocky Connell story. Let me tell you about the date I had where a woman stopped me right in my tracks during the date and said, does this cocky bullshit really work on women?

I had been seeing some positive improvements. I was finally getting out of the friend zone on a lot of first dates. not all, but many. And what had been working for me is being cheeky, being a little bit cocky. I am an authentically kind of cocky. I'm not a cocky guy. Actually, not at all. I'm a very solid, nice, kind guy, I like to think. But I have a smart ass side. When I was in college, my freshman year, I won Mr. Smartass. You know, they gave out like Dorm Awards. I won Mr. Smartass. They give out like Mr. El Niter, Mr. you know, future millionaire.

I got Mr. Smartass. So I'm a natural born smartass. So my smart ass side started to come out. And I saw some really good things happening on first dates. And I think it works so well for me because that's authentically who I am. And I thought, well, if a couple pills of smartassery are working on dates, let's take the whole bottle. And I had a first day to the lounge with a woman I met on Match. And I just hit her with so much cocky, cool, BS.

I was saying things like, you know, oh, you don't like XYZ TV show. Oh, it might not work out between us. There was a lot of that. There was a lot of, excuse me, my eyes are up here. Don't treat me like a piece of meat. A lot of that cocky nonsense. And a little bit of that goes a long way, but I was giving her a lot of it. It's one thing to take a couple aspirin.

It's another to take the whole bottle. And at one point, it's only like 20 minutes into a date. And I'm 20 minutes into this date with this woman. And I remember she looked so much like Jessica Alba. That's why I wanted it to work a little too much because she's so beautiful. And about 20 minutes into the date, she said, does this work on girls? And I said, what do you mean? And she said, this cocky bullshit, does this actually work?

Because I don't know what you're doing here, but this does not seem like normal talking. And I'm like, what are you talking about? This is normal. Cocky, cocky, this. And the date was essentially over at that point in her mind. I had no chance. It was done. But it was a really valuable lesson.

And the takeaway I want you to have is ignore the toxic bullshit guys who are like cocky, smooth. play it cool no just be vulnerable just be real let that genuine vulnerability carry the day for you because cocky does not work if it's too too much of a good thing becomes its opposite it becomes a bad thing anyway that was a valuable lesson for me and let's go to oh here's a good one I call story number seven I call this interview mode. Let me tell you about, and this will probably resonate with a lot of you out there. Let me tell you about one of the biggest flirting mistakes I ever made, which was falling into interview mode, something you probably know very well.

I had a first date. Also, I believe it was a Tinder date with a woman named Deborah. and back when I first started working on my dating life, I was a journalist. And so asking questions was one of my strengths. And I used to think, well, you know what? I do really good at work asking people, asking my interview subjects questions. I'll just ask the most amazing questions in the world. And I had a date with this woman named Deborah.

And I just interviewed her. like she was going to be on the cover of Time magazine or on 60 minutes. And some of the questions were good. Don't get me wrong. But it was such an interview. It wasn't just like, where you from, what do you do? It was like deep, deep, analytical, almost like therapy types of questions. And I just started going to therapy at that point as well in my life.

So I was really into like going deep, learning about a person's psyche. And at the end of the date, she said, you've asked me like 50 questions, but you haven't told me a single thing about you. And she wasn't complaining. She was just calling it out. And the date ended. And I asked her out again. And she texted me a very wonderful, sweet, heartfelt message.

She said, look, I got to be honest with you. I just don't have a sense. for who you are. I'm not sure that we're a good fit to date just because I don't know anything about you. And it was nice having the conversation, but I just felt like I was being interviewed. She literally used that word. And that was an eye-opening moment. It stung, but I learned a valuable lesson about dreaded interview mode. And so here's my lesson that I want you to take away from this. And it's a little bit paradoxical. It's a little bit paradoxical. It's It's okay to ask questions on first dates, but you don't want to be the only one asking questions,

and you don't want the questions to be overly informational, but nor do you want questions to be deep dives into her psyche. Think light, fun questions. So my advice here is not to not ask questions, but you want to ask questions, but you want to ask light, playful questions. The questions that are easy, breezy, fun hypothetical questions, questions like, what do you love to do for fun? Questions like, if we could travel anywhere in the world together, where would we go?

Now, that's a question I asked on many dates down the road once I figured out first dates that women love the, women love questions like, if we could go anywhere in the world together, we could be instantly transported right now. Where would we go? And why? That's a great question. I've had great success with the question, who should play you in the movie of your life?

What actor? Who should star in the Jennifer Smith story or whatever her name is? That makes women think in a light way, in a compelling way. So don't be afraid of interview mode. Be afraid of deeply deep psyche type question. and be afraid of only interrogating her with logical factual questions.

What do you do? Where did you go to college? What year did you graduate? When did you start that job at that law firm? How long have you been there? What kind of law did you think about practicing? If not that one, women don't want that. But they also don't want that deeper psyche stuff.

I have a client. I'll call him Brad, not his real name, but Brad is. currently working with me on going less deep with women. He's been hearing a lot of, you're a great guy. You're very attractive and very datable, but gosh, you're intense. That's a little intense for me. That's what Brad has been hearing when he came to me for coaching. So I'm coaching Brad and let's keep it light, fun, playful. That's generally the first date vibe you want and that's a valuable lesson I learned when Deborah said Connell she didn't say intense she said Connell I just felt like I was being interrogated the whole night I don't want that so thanks but

no thanks to the second date learn from my mistake please learn from my mistake okay thank you so much for listening I have many more mistakes I made maybe I'll do a part two seven more flirting mistakes I made over the years but I made them and I learned something and I guess that's a last thought I'll share with you. A lot of my clients beat themselves up when they make a mistake. And I don't want you to, whether you're a listener or a client, don't beat yourself up. Every date, every approach, every interaction you have with a woman, think of it as win, learn, not win, lose. If you look at every date, every approach, every text exchange as win, lose, oh, you're going to be covered in bruises. you're going to be giving yourself these bruises.

You're going to be beating yourself up left and right. Don't look at dates that way. Look at interactions with women as win-learn. It's a win if she giggles and laughs and the date goes well. Or you feel good about where it's going. That's a win. But it's not a loss if that doesn't happen. It's a lesson.

And if we turn dating from win-loss into win-learn, oh, man, your mindset stays more positive. it's easier to take that right forward action and you'll get a girlfriend all the faster. Okay, until next time, thank you so much for listening.