How to Get a Girlfriend with Connell Barrett - 5 Flirting Moments that Broke My Brain (and Rewired What I Thought Was Possible)

Episode Date: June 23, 2026

When you get good at flirting, you’ll be shocked by what you can achieve. Dating coach Connell Barrett sure was. Once a dateless introvert stuck in the friend zone, he never imagined his love life would include instant make-outs, fun flings, and beautiful women pursuing him. In this episode of “How to Get a Girlfriend,” Connell shares five brain-breaking flirting moments that shattered his dating limitations. What might be possible for you?03:11: “You Want Me to Approach Her? She’s with that Guy!”09:39: Three First Dates, Three First Kisses18:20: Why So Many Women Prefer Older Men24:54: The Date that Truly Broke My Brain36:17: How to Manage a Ménage: It’s as Easy as One, Two, “Toi”NOT SURE HOW TO TALK TO WOMEN YOU FIND ATTRACTIVE? 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)

I texted her, hey, I just wanted you to know that you had a good time last night and you want to see me again. 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 and connect with women in a really authentic way without having to use sketchy, weird pickup artist moves. Because mom was right, women like you for you. And your dream girl will like you for you. Let's have some fun today. I want to tell you about five flirting moments that broke my brain.

These are moments when I saw what's possible with women and flirting and connecting. These are moments that made me say, wait, what? That's possible? Before I go into the five brain-breaking flirting moments, first I want to give you a little background on me. If you don't know me well or if you're listening to this for the first time, I came from a really low place with women. I was not good with women.

I'm naturally introverted. I went to an all-boys high school. I barely dated in college. In my 20s, I had one girlfriend. And I settled for her. And she settled for me, by the way. It was a mutual settling. And I didn't think I could find anybody else who wanted to be with me.

So we got married. And that ended very much. briefly thereafter, only nine weeks later, because I was making dating choices from a place of scarcity. And I was pretty much dateless into my early mid-30s. And that's when I said, okay, I got to figure out my dating life. I've got to figure out why am I that guy who's always in the friend zone? Why am I that guy who struggles? So I came from a really low place, a place of self-doubt, a place of loneliness, and feeling like, you know what, I'm just not that guy, women like. I'm the guy, a girl's a friend with, but then she wants to date or hook up with the cooler,

more outgoing guy. So it wasn't until after I went on this five, basically a five-year journey of hiring coaches and taking a lot of action that I figured things out. So these five stories are mile posts during that five or six years stretch before I became a dating coach while I was learning to get really good at flirting and dating. And so, yeah, there are five moments that made me go, wait a minute, maybe dating and flirting and connecting with women isn't what I thought it was. So here we go, five brainbreaking moments in flirting and connecting with women.

And stick around to the second to last one. The story with Natalie, I think, is going to really blow your mind because something happened on a first date that I thought was literally impossible. So a little teaser there. Let's start with the first story. So I'm in London and I was there working with a dating guru who worked out of London at the time, East End of London. And I had just begun approaching women. I was still nervous and unsure about how to do it. I'd had some success, but not very much. And so I'm in London and my coach who went by the name of Ozzie, I think that's his real name actually.

And Ozzy said, okay, go approach that couple over there. We're in a club, in a bar, in the east end of London. And I see a really pretty blonde talking to a bloke. And their fingers are intertwined. They're making googly eyes at each other. And they're clearly a couple. And he said, go approach them. And I said, what are you talking about?

Why would I approach them? And he said, eh, give it a shot. Why not? He didn't mean go hit on her. He just meant be social and go talk to people. So I approached, by the way, no pressure. I felt no pressure counterintuitively, even though I was approaching a couple who were all into each other,

that in a way that took all the pressure off because there was nothing at stake. So I walk over. I say, hey, guys, what's up? how's your night going or something generic like that and the craziest thing happened he got really nervous this guy he pulled his hands away from her and he started to get a little bit nervous and talking quickly hey what's up mate how you doing oh where you're from you don't sound like you're from here talking really fast and i watch her watch him watch me and i can see this really interesting dynamic happening where he is talking a lot he's nervous he's in his head and i see her look at me

and give me these big eyes and i basically ignore him and i start talking to this really cute british girl cute british blonde i forget her name it's been many many years i have no idea what her name is and next thing i know she and i are dancing talking kissing and she's she's all over me, we're all over each other, maybe five or six minutes later. Where'd the guy go? Well, once he realized she was into me, he just wandered away. And early in the interaction, I realized, oh, they're not a couple. They had met five, ten minutes earlier. The connection that two people have in a nightclub on a Friday or Saturday night, it's very tenuous, at least for the first five or ten minutes. A couple, two people might look like they're together and they're

just they just met. And that was a really big brain-breaking moment for me. I realized that it's okay to approach a couple. You can walk up to a man and a woman in a bar in a nighttime venue. Don't get me wrong. As a dating coach, I would say gravitate toward cute girls who are by themselves or with female friends. Don't try to approach men and women. But you can walk up to a woman who's with a guy and you just never know what the what the situation is and again what was crazy is i didn't do anything i just walked up and i was myself and i think that's what made her attracted to me also keep in mind i'm an american new yorker and maybe i was like a unicorn at that london east end club and that might have made me seem like the shiny object the bottom line is he he was gone he disappeared he could see

that she was into me. And she and I were together for a little while. I didn't like leave with her or date her. Nothing crazy happened that night. I wish I had some amazing story of my romantic conquest that night. No, it was just, she was with me for 15 or 20 minutes. I got her number, I think, and that was that. But man, that was fascinating. What really happened there was she looked at two men and I was more comfortable and relaxed in my own skin because I had no outcome attached. I didn't think there was a chance of anything good happening. So in a way, that relaxed me and that was the best thing that could have happened to me. He was the one who was overreacting to me.

That was a really powerful lesson. I learned because sometimes I would be talking to a woman and a guy would come up to us. And I always remembered that lesson. I said, don't do what the British guy did that night. don't get overly defensive, don't talk fast, don't try to distract away from what's happening or how I'm feeling. Just be grounded in the moment. So that was just a moment where I thought, damn, you don't really have to do anything with some women. Just be really grounded in who you are, and that's enough for some women. And it's okay to go say hi to a man and a woman who are at a bar

or a club. There's nothing wrong with that. Use common sense. Don't hit on her if she's with a guy. Here's a quick bonus tip. If you do approach socialize with a man and a woman at a venue, one of the first questions you should ask is, how do you two know each other and always ask the woman? The guy will lie to you. So that night in London, I believe, maybe about 30 seconds in, I said to the blonde, hey, how do you two know each other? And she said, oh, we just met. And now I had the intel that I needed to know. I would never have, you know, flirted with her or showed that romantic interest. If she had said that was her boyfriend, that would be really effed up on my part. So this is a really important question to ask. How do you two know each other? It's a great question to ask a woman when she's with a guy or a guy is standing there in her

presence. That way you understand what the dynamics are. But that moment broke my brain. If you would have told me that, yeah, I can approach a quote-unquote couple. And two, three minutes later, she leaves her for him. Whoa. Brain broken. Brain broken. Okay, let's go to brain-breaking flirting moment number two. This story is called three dates, three makeouts.

And this was around the same time. I'm just really taking action, figuring out my dating. I launched an online dating profile and was able to get enough good matches, enough to work with. I'm lucky in that I live in New York City and have for over 25 years. So if you have a reasonably good profile, there's a limitless number of dates in a big city, which is a nice bonus. So this brain-breaking moment was the benefit of a big upgrade I had in my flirting, my communication on dates. I'm a natural-born smart ass. I'm very playful, very sarcastic.

But I was hiding that on dates. I was hiding it. I was being very much overly supplicating, try-hard. guy on dates. I got and I got put in the friend zone a lot early on. You know, I'd lean forward and hang on her every word and just hope, hope, hope that a given woman liked me. And that rarely worked out. And so I remember when I started to really embrace this idea of authenticity, what does that mean? Well, it means channel your true personality and part of that is your true sense of humor. And my true sense of humor is I'm a smart ass. I loved Letterman. I grew up

loving David the David Letterman show and his kind of snarky, sarcastic humor. That was me in high school, so much in high school and grade school and college. And I just sort of developed a natural smart ass side. My freshman year in college in Indiana, they gave out dorm awards, you know, like Mr. All-Nighter, Mr. Party Animal. A lot of dorms used to do that back in the day. I don't know if they still do. And I won Mr. Smartass. Clearly, I'm a smart ass.

But I was hiding that side on dates. And being cocky and cheeky, it's not for every guy, but if that's your genuine personality, you want to let that come out. And I'm a cheeky smart ass. And so I started showing that on dates. And I remember this one week when I really started getting momentum, I was really letting that smart. hard-ass, cheeky, borderline cocky side come out. And I could see women looking at me differently

than they had been. And I remember I had one date with a woman. And I came up with a couple funny lines. I think they came out in the moment. Her name is Katie. And I remember our first date, my first of these three dates. So I had, sorry, sorry, let me back up. I had three first dates lined up in three successive nights, Thursday, Friday, Saturday, all from online dating. So full dance card. I was super excited about that. And Thursday night was Katie. And I remember she kind of fiddled with her phone and kept dropping her phone or like dropped

her phone twice. And I teased her about that. You know, I said something like, oh, why do I love? like such cute, dorky, clumsy girls. You're so clumsy. You're like a rom-com character. And she giggled and liked it. And I could see how women were responding to my snarky, playful, teasing comments. Now, your mileage may vary. Every guy has to find his own style, but that's my style that I could see working. And we made out. I remember I was walking her to a taxi. And I never had a woman say this to me. She said, she made it clear. Here's what had been happening. What had been happening

is quick, dry hug, or sorry, quick hug, no kiss or dry cheek kiss, and then she walks away, clearly no interest. Katie was different. I walked her to the right street corner waiting for a taxi, and she turned to me and smiled and said, you really want to kiss me, don't you? Which of course is code for, I want you to kiss me. And even I back then could take. take that hint, and I kissed her. And the next day, I kept the cheekiness going, the snarky, smart-ass side. The next day, I texted her as something that I still teach my clients all these years later. I texted her, hey, I just wanted you to know that you had a good time last night and you want to see me again. And Katie and I dated for a while. And she later told me how she loved that text

message that made her smile. She said she was watching her phone. or she was with her girlfriend when that text came through and they both they both laughed anyway so that was date number one make out with katie adorable katie and then the second night i think the second night my first date i forget her name it's been many many years but again similar vibe met at a bar couple drinks i tease i joke we had a really nice kiss at the end of that date and then the third night i remember this woman's name is elizabeth very petite very petite a little bit shy and very pretty, very smart. I love smart, brainy women. I always have. And I remember that third date with Elizabeth. Again, I could tell she was into me. My confidence had been growing

so much. I just had back-to-back really good dates. I had a couple drinks, a couple strong beers. I drank at the time. And made out. Great, sexy make-out. And I remember walking home. I live in New York city where you can walk so many places. I remember walking home from that date, had a little buzz going. And I just thought, wow, Connell, three dates, three makeouts. Clearly three women all want to see me again. Boy, I didn't know this was possible. I thought that women just didn't like me or that very few and far between women liked me. And that was just a pretty incredible week where I went three for three, so to speak, after, you know, well, 30-some years of being alive and decade and a half of dating or trying to date,

finally having some real measurable rewards and wins, three back-to-back dates, three first kisses, three great sexy makeouts that broke my brain. The closest thing to a magic bullet, and there's no such thing as a magic bullet in dating, but in terms of flirting, the secret weapon I was discovering was when I combine the right combination of cheeky snark with sincerity and just being conal, being warm and normal, but also smart ass. Gosh, a lot of women really like it. And three in a row was a pretty big brain-breaking moment. By the way, as you might know, I'm a dating coach. I do one-on-one personalized coaching. All my clients, we work one-on-one together.

And if you would like to have brain-breakingly good dating results, then go to my website, datingtransformation.com. You can book a free call to talk to me about how my coaching works, and I can share with you sort of, okay, here's what's holding you back. Here's what you need to do to get more dates, to flirt better, to approach, to get out of friend's own. Maybe it's online dating. Sometimes I overhaul a guy's online dating profile. Basically, I help guys get girlfriends and help them get dates in a girlfriend. So if that's something that you might be looking for, go to my website, datingtransformation.com. Book a free call with me.

If you're not looking for coaching, totally cool. Most guys aren't. I still want to give you something. Email me, Connell at datingtransformation.com. A subject free book. And I would love to send you a free copy of my dating book. Dating sucks, but you don't. Came out a few years ago, and it's basically a roadmap about how to date with authenticity, what I call radical authenticity, being yourself. It's how to channel that on dates and on your profile. And anyway, you can email me, free book at Connell at datingtransformation.com, and I'll send you my free book. No strings attached. also my emails on the show notes as well okay let's go to brainbreaking flirting moment number three

what's a good one for number three here's a good one this was a brain breaker for me this happened a few times but this is a memorable moment to sort of sum up a larger a larger narrative it was about a year before the pandemic so 2019 i'm in san an san anna monica with my client edward Edward hired me and I became his coach and we did in-person coaching in Santa Monica. And we're at a place called Bungalow in Santa Monica. I think it's still there. I haven't been there in a few years. But we're at Bungalow and Edward is, I'm Edward's wingman.

I'm his wingman for the night. And it's like, go approach these girls. Go say this. Go do that. And I had him approach some girls sitting on the couch at Bungalow. And at the time, I'm 48, I think, 48 at the time. And Edwards talking to these women, and I'm being a wingman. And I'm talking to one of the women in the group of girls he's talking to.

He's talking to one of the girls. And I'm talking to one of the other ones. And I remember her saying, I remember saying, I remember saying, I remember grabbing her number and she said yeah she said here's my number and then she just looked me in the eye and said by the way I want you to know I really like older guys oh I remember we played a little age game I would play a little game sometimes women would ask me how old are you and I'd say hell do you think I am play a little age guessing game which can be fun for a lot of women anyway we've I think we played that game and she was one of the rare women who guessed my age pretty close I'm um um uh

fairly fortunate in that I tend to be told that I look younger than my actual age. I've always looked about five to ten years younger than my age. Thank you, dad and mom, for the good genes. And this woman at Bungalow, we played that game and I said, how old do you think I am? And she said something like, I think she guessed it either right on the number or pretty close, like 47. And I was like, damn, you nailed it. And I remember she looked at me and said, that's okay. I really like older guys and she sort of leaned into it. And I want to say she's probably mid-20s. And that represents a larger brain-breaking moment I've had, which is that older men, as a general rule, get more attractive to younger women. And I want you to know this if you're a guy who's, I don't know,

approaching 40, wondering, oh, man, is it over for me when I hit 40? Is it over for me when I hit 50? is it over for me when I hit 60? Whatever number you're approaching, I want you to know that, gosh, older guys are so attractive to so many women. That was a brain-breaking lesson that I've learned many times. You might think that being an older guy disqualifies you. That is not true. If anything, it makes you more attractive.

And even if it doesn't make you attractive to more women, it's going to make you more attractive to a significant subset of women. So many women who like older guys. My girlfriend, Jess, and I have a 28-year age gap, I think. Is that right? Yeah. She's 33. Is that right?

No, I'm sorry, 22. I suck at math. 22 years. Not 28 years. You're like, geez, Connell. No, 22 years between myself and my girlfriend. And not that it's about age, but she likes older guys. Or at least she likes the traits that often come out in men who have lived a life.

lived a bit of a life. And I remember I dated a woman. This was also right before the pandemic. So I remember it was like I was beginning to approach 50. And I was thinking about it a lot. I was like, oh, no, I'm almost 50. What happens when I turned 50? And I had a short little fling with a woman who was in her 20s.

And she showed me some. I forget if it was Instagram or, TikTok, but she showed me some giant online group of women who like daddies, women who like older guys. And there were like 400,000 people in this group. I forget if it was TikTok or Instagram or what it was. But it was something online. She was basically saying, there's so many younger women who like older guys. And so that has broken my brain many times. Are there some women who want to date their age or close to it? Hell yeah. Absolutely. There's that too. Think about age. Your age is like any other part of dating. There's all kinds of bias baked into dating. You know, there's bias about height, about age, about skin color, about ethnicity, about wanting kids, wanting kids. Just think of age as another data point of bias, but it's not a disqualifier.

So don't forget, if you're turning 40 or 30 or 50 or whatever age you're intimidated by, take it from a, Take it from double nickels here. I'm 55. I turned 55 back in May. My sister said, hey, happy double nickels. And I thought, that sounds pretty cool. Call me double nickels. But take it from Mr. Double Nichols,

generally, there's a lot of truth to the idea that as a guy gets older, he gets more attractive. Not to all women, but to a lot of women. There's definitely a large niche of women who are like, I want me a, what's the term, Zaddy? I want a Zaddy. Okay, let's get to story number four. This is the one that broke my brain bigger than almost any brainbreaker. I can tell you.

I want to tell you about Natalie and one of the most holy shit brain-breaking first date experiences I ever had. This goes back to when I was getting competent and starting to see some good results. So this is after my three dates, three makeouts story. I met Natalie. And again, I want to pause here. I hope this doesn't sound like, oh, God, Connell is bragging about another win. Man, I had so many losses along the way. Please keep that in mind.

I had 30-some years of dating losses and friend zonings. And, oh, man, I was on a date once, and the woman was so not into me, she left the date and went over to another guy at the bar. That's how bad things got for me. So keep that in mind. This is not an ego trip for me. I want to share with you brain-breaking moments so that you can have breakthroughs. You can have hope.

You can have some guidance and hope. Anyway, so I'm getting in a really good stuff. I'm getting really good at first dates at this point. This is predating coach, but I'm getting really darn good at this. and get a match on a dating profile and Natalie. Late 20s, I'm in my 30s at this point. Late 20s, brunette, chef, beautiful chef. Imagine like a hot, sexy chef on a TV show.

I don't know. Monica from friends. Or imagine Carmi on the bear. I don't know. is flirting with a beautiful chef. She was that kind of, that kind of person. And we matched. And we did a pre-date phone chat, kind of like a vibe check.

And we get on the phone the day before our date. And she said, hey, you know, nice talking to you. I'm looking forward to tomorrow. And then she said to me, by the way, just so you know, the last four or five guys I've met, I haven't clicked with. So, you know, no offense if it doesn't work out. I just wanted to give you a heads up. It was almost like a preemptive friend zone.

And she wasn't doing it as a move. She wasn't doing it in any kind of way to get me in my head. She was trying to give me a heads up because this is a beautiful girl, successful, well-dressed, stylish chef, or like a sous chef at some fancy restaurant. It was down in Tribeca, I remember. And she was trying to give me a heads up. She was trying to say, hey, dude, probably won't go anywhere. She told me that the last guy she had a date with, she couldn't date him because I remember this detail.

She said he was holding the umbrella and he whined that the umbrella was heavy and his arm was tired. And that was it for him. I do remember that detail from all those years ago. That's what Natalie said. And I don't know what to do with that information. I just thought that was a memorable detail. If you hold the umbrella, don't whine about how heavy it is. There's your tip right there.

So anyway, we have our little pre-date chat. Next night, I'm waiting for her. I was really good at picking spots. Dark, moody bar called, I think it's still there in Tribeca, called the room. Wonderful bar called the room. Or maybe the other room. I think it's the room. And the room, it's like dark candlelit.

but not like over the top romantic candlelit, more like just kind of like neighborhood dark and a little bit grungy, a little bit classy, wine and beer bar. They had cocktails too. Anyway, really good spot for a date. And you have to sit next to people. That's what I like about it. It's like it's set up with sofas and seats all next to each other, no sitting across, which is great.

It's why I picked it. It was a really good first date spot. Anyway, Natalie arrives, looking beautiful, looking gorgeous. She gets there. She sits. We start chatting for five, ten minutes. And then she starts telling a story about, I forget if it was shoe shopping or makeup. She tells like a kind of a girly girl story.

And I'm listening for three or four minutes. And I'm trying to be a good present, active listener. But it's a really boring story. It just is. and I didn't have a coach at that point, but I did have enough. I had consumed some good advice from some online people, coaches. And I remember one coach saying something like, take control of the date. Be the man.

Take control. Or take responsibility. He didn't say take control. Take responsibility for what you do talk about. And I thought that was really good advice. I like that idea. Lead. And so I said this.

I interrupted her and said, hey, can I be honest with you? I've totally lost interest in your story. But listen to what happened to me today. And then I went into a story about whatever I wanted to talk about. And I vividly remember the look on her face. She cocked her, she cocked her head a little bit. And she looked at me. She shot me a look that said, did you just interrupt me?

and like tell me I'm boring. She didn't say that, but she looked at me that way. And it was the most interesting look. It was a combination of, oh, no, you didn't with, damn, I'm impressed. It was this interesting cocktail of both. And I got to be honest, it's been many years, but I'm sure I was nervous. I know I was. I was not like Mr. Confident. Remember, I'm coming from the most friends-owned, lonely, never-dated,

largely dateless guy. I never used to say stuff like that. I'm a nice boy from Ohio. I never told women to stop talking. I'm going to talk now. Not that I said it that way. But bottom line is it was a risk. It was absolutely risky, but it had an incredible effect because it, I survived. She didn't walk up and leave. I stand up and leave. I talked about the thing. And I think the reason she was attracted to it was because she said, finally, a guy who takes the lead. And I think, I'm pretty sure, because the date went great, that she realized, oh, he's taking charge.

I like that in a man. And I did other things as well really well on the date. teasing humor. I'm sure I teased a little bit. I'm sure I cracked some jokes. But here's what I remember. And I remember about 15 minutes in, she threw her leg over my leg,

like in a very casual way, kind of like we're on the couch watching TV at home, except we're in this bar, a very casual thing to do, physical touch that she was initiating. And then, you know, the chemistry amped up. And about 20, 30 minutes later, she crawls across me and sits on my lap and says, I think I want to sit here.

Oh, I remember what she said. So I told a story, a true story from my childhood about how I'm, my joking nickname for me as a kid was Miracle Baby because I'm the youngest of six. And I was the unexpected surprise Redhead. And I said, you can call me Miracle Baby. And I remember she crawled across the couch and sat on my lap and said, I want to sit on Miracle Baby's lap. And then, of course, at that point, not much. There's no bigger indicator of interest than a woman sitting on your lap. And my confidence is rising, among other parts of me.

And at one point, and her top, she wasn't wearing a low-cut top, but she was wearing a white top that had a little bit of, like, air between the collar and her skin, so a little bit of movement. And she said, you know, if you're good, I'll give you a peek. She was being very childlike. Sorry, not childlike, not childlike, but girlish, very girlish. She's like, do you want a peak miracle baby? It was like that. If you're good, I'll give you a peek.

And completely different energy than the woman I talked to on the phone the night before who was like, hey, just so you know, the night before it was like, just so you know, you're probably in the friend zone. And now it was like, so a miracle. baby, want a little peek at my cleavage sitting on my lap, we kiss. Even I can take the hint that I can kiss a girl if she's sitting on my lap. We kiss and make out, the bartender and a couple other people are looking at us like, dude, guys, get a room. Jeez. And it's like 90 minutes into a date, maybe an hour into the date. And it was going so well that she, while sitting on my lap, she said,

oh, I know what we should do for our second date. We should go get a massage. She had gotten, oh, this was right after Christmas, and she had gotten a gift card for a massage and said, oh, we should go get a couple's massage together. Wouldn't that be a nice? And I might give you a peek, meaning a peek at her top. Very flirtatious, girlish. I've never had a woman that into me, certainly on a date, not a woman that beautiful and not such a total 180 from what she was warning me against on her. phone call the day before. And again, made out, great second date. We did date for a while. We had a short-term fling. It wasn't meant to be long-term, but very much a successful, a little fling.

And talk about a brain-breaking moment. And to me, the big lesson, by the way, I want to be really clear about something. Do not try this at home. Do not just tell women, hey, I'm talking now. don't say I've lost interest in your story. And now I want to tell mine, don't do it as a move. I wasn't really doing it as a move. I was doing it because I was really understanding, I was beginning to make my new religion just tell the truth, be yourself, speak in the most unfiltered way you can.

And I was literally just speaking my thoughts. That's why I talk so much about authenticity is I'm just speaking my thoughts. there is just as good of a chance that she or another woman would have said, how dare you tell me that you, that was rude and it could have blown up. It would have blown up with some women. It's just that with Natalie, it absolutely worked. So the lesson here is don't tell women to stop talking.

I wouldn't advise that, frankly, to anybody, including myself, if I was going on dates. But the point is that Natalie finally met a guy who was taking the lead who had the strength, the confidence to say, hey, your story is not helping the date. Let me tell a better story. And I sense that she understood I was doing it for the greater good. I was doing it for both of us. I don't want her to have a boring date with me. I don't want to be friends-owned.

She doesn't want a guy who just sits there and nods and nods and listens and says, I hope she likes me. and that's why she sat on my lap and kissed me and invited me for a second date of a sensual massage. So that was definitely a brain-breaking moment for sure. Okay, brain-breaking moment number five. This is in my book, but I'll tell it real quick. I was dating a woman, I'll call her Amanda, and I'll just be really honest with you. I had never been with two girls before.

What is most every straight man's dream to at least once have a menagerie? I love that episode. I love the episode of Seinfeld where Jerry's like, I think it's pronounced menage a three. I'd never had one before, and I'm dating a woman named Amanda. And we'd already hooked up a couple times. It's early days. and I didn't see it going long term, but I still liked her.

We were having fun. So I said, you know what? I got nothing to lose. One Sunday afternoon, I sent her a text message. It read something like this. The exact words were in my book, but it went something like this. Hey, Amanda, I have an idea. I have a question.

I would love, I've never been with two women at one time. and I would love to experience that with you. If that's something you might be open to. If it's not, it's totally cool. I just feel like doing something like that would be incredible, especially if it was with you. What do you think? And then I sent it.

Was I afraid to send it? Oh my God. I was terrified. Am I a creep? Am I a sex? Sex fiend? A sex obsessed guy who just wants sex. and threesomes and orgies.

No, I'm not, but I felt that way when I sent that text message. And I sent it, I don't know, 2 or 3 p.m. on a Sunday. I just remember it was a Sunday. And, you know, check my phone every so often. No message from Amanda. No message. No message. Three, four, five hours pass.

And gosh, it must have been like 9, 10 p.m. I doze off. And at this point, I'm thinking, well, you screwed that up. she thinks you're a creep and a sex-obsessed loser and you're never going to hear from her again. And at about midnight, maybe 1230, my phone's ringing while my bell for my apartment is being pushed. And I'm like, what's going on? I wake up. I look at my phone.

I see Amanda's calling me. I'm like, okay, well, I think this could be good. and then turns out she's downstairs in my apartment complex trying to wake me up. Like texting me, are you there? Long story short, she showed up with a girlfriend of hers for a three-person hangout. Let's call it. And all I did was send the text message. And I was not expecting that to happen.

I thought she might, if she was open to it, I thought we would talk about it, we would maybe have a conversation, she might know somebody. I also thought she might tell me, hell no, weirdo, I don't want to have a threesome. I want to date you. That's not what I'm into. My big lesson here is it was about taking a risk and asking for what I wanted. And that, to me, that speaks to a larger lesson that I've learned so many times and shared with so many clients, look, this is not about threesome. Your life isn't going to change if you ever have a threesome. It was wonderful, but I was still me the next day. And I mean, with problems and rent-to-pay and a boss on my butt. But I'm so glad I did it. I think every guy who wants to

experience that should experience it if he can find two willing participants. And what What an amazing outcome. And all I did, all I did was send that text message. Hey, basically, sweetly, nicely. How about a threesome? For what it's worth, if you want the secret sauce of what made her, I think, want to do it, is the way I phrased it was, hey, I want this to be something we experienced together. You, Amanda and me, Connell, and then, obviously, that resonated with her.

and I was not expecting in a million years you would just show up with a like a singing telegram, a threesomeogram. Oh my God. I would never have imagined that. So that was a brain-breaking moment, not just because of the rewarding outcome was what really made it happen was just asking boldly can create opportunities that you never thought might have happened if you play it safe. And I'll leave you with that final thought here. we need to take risks. Take them with intelligence.

Take them with empathy. Take them with kindness. Use your head. But you've got to take some romantic risks. You have to be willing to be told, no thanks. I don't want to do that. Or whether it's an approach you want to make or going for a kiss on a first date or giving a woman a compliment and being afraid of,

getting rejected, we have to take romantic risks. Whether it's a G-rated, sweet, first-date compliment you want to give or a raunchy text message looking for a threesome or anywhere in between, we've got to take those courageous, authentic risks. If I could take everything I teach and boil it down to one sentence, it would be take authentic, courageous romantic risks with a lot of kindness and empathy toward women, but you've got to be courageous. You've got to take chances. And anyway, that was my final brain-breaking moment. Stick around. I'm going to do part two, another episode, five more brain-breaking moments.

In part two, they're not going to be my stories. They're going to be client stories. You're going to hear about some amazing brain-breaking, flirting moments of dating and flirting moments. Incredible wins. Incredible obstacles. My clients overcame that led to incredible brain-breaking wins. So that will be the next episode. Until then.