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5 “Aha!” Moments that Took Me from Dateless to Dating Wonderful Women

Featuring NYC Dating Coach Connell Barrett
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Learn how to go from dateless to dating.

The reason dating coach Connell Barrett can fix any dating problem is because he had EVERY dating problem—and he overcame them. In this episode of the Dating Transformation podcast, Connell shares 5 game-changing “Aha!” moments he experienced that helped him get great at flirting, approach women with confidence, escape the Friend Zone, and more. Listen now to learn how to go from dateless to dating in no time.



"I used to believe playing it safe was smart. However, in dating and relationships, safety is risky and risky is safe."

-Connell Barrett

Featured in the episode

Connell Barrett
Founder and Executive Coach of DatingTransformation


00:00 - Taking Risks in Dating Is Surprisingly Safe
05:09 - Courageous Moves: Man Gambles on First Date
06:12 -  The Safe Bet on Taking Risks in Dating Approaches
07:18 - Bold Gesture: Risking Rejection by Tapping Her Shoulder
12:11 - Embrace Authenticity: Not Everyone Will Connect with You
15:15 - Transforming Fear into Confidence in Dating Encounters
16:37 - Genuine Connections: Sincere Communication Over Flirtatious Behaviors
18:00 - The Art of Flirting: Balancing Sincerity with Playfulness
20:58 - Unleashing Playfulness in Relationships
21:31 - Playful Dynamics: Debunking Dating Myths Online and Offline
24:40 - Substance Over Style: Personality Draws in High-Quality Partners
26:11 - Outro

Produced by Heartcastmedia

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Connell Barrett:


Welcome back to the Dating Transformation podcast. I'm your host, dating coach Connell Barrett. I'm here to help you let me start over again. Sorry, Matt. Welcome back to the dating transformation podcast. I'm your host, dating coach Connell Barrett. I'm here to help you learn to flirt, gain confidence, and attract an incredible partner, one who loves you for your authentic self. And that's the keyword, authenticity.Success with women is about understanding what doesn't work and understanding the core essential things that do work, and it starts with being radically authentic, showing women your true best, most confident self. And today's episode is gonna be a fun one because I'll bet that you play it safe on dates. I'll bet that you would love to approach women, but you never do because you just don't have the confidence. I'll bet that you try to impress women. Maybe sell yourself to them. Maybe even try to be somebody you're not. Cause, Hey, maybe she likes that version of you, not the real you. And or you might be struggling with good old fashioned not knowing what to say, how to flirt, what flirting even means, and how to make sparks happen with women on dates or online or in a conversation.

Let's do it. What are we gonna talk about today? I'm gonna share with you 5 of the biggest moments I have had in my dating life and that a couple of my clients have had. And I want to shatter some myths and give you the truth. So that's what today's episode is about. I'm gonna give you 4 or 5 myths that we're gonna take a sledgehammer to, and then I'm gonna give you the truth. With some practical tips, you can go out there and flirt with confidence. Approach and know how to do it in a way that gets results and, in a way that does it with charm and authenticity, not being somebody you're not. So let's get to it. Let's go through let's count down.Let me list 4 or 5 of the biggest moments I had. Here's the first here's a big moment I had once upon a time, which is I used to think that playing it safe was smart, but actually playing it safe with women and dating is risky, and playing it risky is really safe. In other words, safety is risky, and risky is safe. For example, if you go on a first date and you literally sit on your hands or figuratively sit on your hands, you never physically touch at all. You never break that touch barrier, or you're afraid to go for that first kiss, you're afraid that saying something flirtatious will make her think you're creepy or a weirdo, then that then you're playing it safe. But the thing is, playing it safe is very risky in that you have a high risk that she won't want a second or third date with you. On the other hand, if you go on a date and you take some measured risks, you say that true, honest, authentic thing. You tell her what you find sexy about her.You go to hold her hand when you think the moment is right. You go for that first kiss when that kiss window opens. Now you're doing something that will feel risky to you at the moment, but it's actually a very safe, smart move to make because that risk is a smart, safe bet in terms of results. If not with her, then on your next date or the one after that or future dates. Here's a couple quick examples. I have a client named Brian, and Brian was struggling with first date kisses. He wasn't even trying. He had never attempted to have a first date kiss in our time working together, and he lost out with some pretty wonderful women.Brian was struggling with he just didn't wanna come across like a jerk. He's a nice guy. He really is. He's a gentleman. And so he had this story in his head that, you know what? It's creepy and weird to make a move. But I said, actually, if you find her sexy, tell her she's sexy. If you want to kiss her, go for a kiss. It's rude not to do those things.

Why are you being so rude to women? Why aren't you going for a kiss? So Brian finally had a first date where he decided to go for it. And he had a couple drinks with a woman at a bar in his hometown, and he walked her out to his car, sorry, to her car. And he still hadn't made a move yet. But he finally worked up the courage and went for that first kiss. And then before you knew it, they were all over each other. In fact, they went from not kissing and touching at all to having a really hot, sexy make out as she leaned against her car. And then they ended up getting into his car and having a hot, steamy, passionate make out in the parking lot of this bar, like a couple of horny high school kids. How did he do it? He decided to stop being safe, which is a risk, and he started taking some risks, which is safe.

So keep this in mind. What you think is safe is actually really risky because you risk a woman looking at you as too timid, as too soft, as too nice. But if you start taking some risks, that's a really safe, smart choice to make. I'm remembering when I first started going out and approaching women in the late double zeros, I re I I had an epiphany. I realized that when I really took a risk, when I committed fully to the approach, it went so much better than the half hearted ones. So a half hearted approach would be like, I remember I was at a oh, here's a good story. I was at Barnes and Noble in New York City at Union Square, and I had done 2 or 3 really timid, safe approaches. What I mean is, like, you know, a woman was looking at the magazine rack or a magazine at the magazine rack.And I was like, hey, what are you reading? Oh, that's nice. I like magazines too. Do do do do do. All right. Well, nice meeting you. Very safe. Very safe. Nothing happened.And I just got so mad at myself. I said, you know what? It's time to take a risk. Time to your time to be a risk taker. And a young woman who looked to be in her early twenties, she walked by me, a gorgeous brunette wearing an NYU sweatshirt. She walked by me, and I just said, you know what? Time to take a risk. And I walked over to her, and I tapped her on the shoulder from behind, which is not necessarily good technique. But you know what? Technique is overrated, and risk taking is underrated. Tapped her on the shoulder.

She turned around, and I said, hey. I just saw you, and you're gorgeous. Had to meet you. Hi. I'm Connell. What's your name? And she looked at me with, like, her eyes and jaw dropped in a good way. She smiled, and she said, hi. I'm name.Let's call her Jen. And long story short, I got her number. We were on a date a couple nights later, and we dated for a while. I took the risk. It felt so unsafe at the moment. So don't get me wrong. If it feels very scary and risky, if it feels unsafe, you're on the right track. And if it feels super safe and too safe, guess what? You're on the wrong track.Okay. Next, Here is the next big moment I had, which is that you might think that you need to impress a woman on a date, but actually what you need to do is express your authentic self. Don't impress by being somebody you're not, Express who you really are at your core. I used to have a huge crush on a woman. I'm gonna call her Laura. And Laura is a beautiful, intelligent, smart, witty, funny, blonde, Great catch. And, we had 1 or 2 dates.

And I remember on our second date, I said to myself, you know what? She's not gonna like me. I've gotta be who I think she likes. And she's a big adventurer. She's into hiking. She's into paragliding and parasailing and all that adventurous stuff. And that's not me. I'm a nerd who likes Star Wars, who likes musical theater, and who likes writing. And I just said, you know what? She doesn't want that.So play up some adventure things. So what did I do on the date? I lied through my teeth. I said, oh, just so you know, yeah. I'm taking pilot training. I'm starting to get my pilot's license. Lie. And, oh, yeah. I'm thinking of swimming with sharks.

I went swimming with sharks once in the Caribbean. I think I'm gonna go down to Belize, swim the sharks again. Double dog lies. And as I'm lying to her, as I'm being somebody I'm not, I feel the sweat just pouring down my forehead. And I don't know if she knew for a fact that I was full of shit, but she could sense something was off. Right. Clearly, I wasn't telling the truth or at least I wasn't comfortable sharing this information with her. Long story short, she is friends with me.

And, that was it for a while. 6 or 8 months later, I'd started working with the first dating coach who really helped me a lot. And then I had another chance with Laura. And Laura and I went on a date, and I was completely different this time. I was authentic. I was being really real with her. I was not trying to be something I wasn't. I was cracking my jokes.

I was cracking dad jokes. I'm a natural born smartass, which is a real good quality to have if that's authentic to you. So I was letting my cheeky, sometimes cocky side come out. Busting her balls a little bit, a lot of banter back and forth. And I said, close your eyes, letting her know I wanted to kiss her. And she got all blushing and bashful, and she said, no. I'm not gonna let you kiss me. And I said, I don't wanna kiss you.

You have cooties. Ew. Gross. And she playfully punched me. She loved the banter and the teasing. And, by the end of the day, we were making out and really having a great date. And I didn't have to be anything I wasn't. I didn't lie.

I didn't give her a bullshit story. Bottom line here is that she already liked me. She liked me before, but I was getting in the way. I was trying to impress her by being somebody I'm not, instead of really leaning into who I am, which is a little cheeky, a little smart assy, definitely nerdy, and putting that self out there. She really liked me once I started being my real authentic self. So please don't forget this lesson. You've got to be authentic. You can't be somebody you're not.

You might not be able to keep it up for a date or 2, but you're gonna get found out just like I did. So put that radically authentic best you out there. Not every woman's gonna like you, but, man, the woman who really likes your type, she's gonna love you. She's gonna go crazy for you. Okay. The next myth I want to bust is this idea of how you, well, a lot of guys want to approach women. And you might want to approach women, but you probably don't do it because you say to yourself, I don't have the confidence. And that's a myth.

You don't need confidence to approach women. You don't need confidence to get results. What you need is courage. You need the courage to take action. Confidence is nice, but it's something you have to earn. You earn it with courage. Confidence is something that comes after you've taken enough courageous action to get confidence. So here's a quick story. The very first night I ever went out to approach women. This is the story that opens my book. It's chapter 1 of my book. I had never approached a woman before in my life. I was 38 years old. I'd never approached a woman. And about 15 minutes before it was time to go out on that rooftop bar in New York City on a July evening in 2009, I had to excuse myself. I had a coach with me, and I said, hey. I'll be right back. I went into the men's room, and I had a panic attack. I got the dry heaves. I started vomiting up stomach acid. I wasn't drinking. I wasn't eating. It was just a panic attack. And at the time, I thought, oh, this is, this is just butterflies. But, really, it was the fear of rejection. It was the fear of finding out that girls just didn't like me, at least not attractive women on a rooftop bar. They wanted alpha males. They wanted badass players. They didn't want nerdy, introverted Jinger Connell. And so it took so much courage that night for me to start going up to women. But with my coach's help and paying $25100, with my coach's help, I just said, you know what? Time to man up and be courageous. And I started approaching women, and I approached and I approached.I had no confidence at the start of the night. By the end of the night, I had some confidence. And most importantly, I clicked with a really wonderful woman named Kelly. And we ended up spending the night together and having a real incredible deep connection and a real fun, sexy night. So I did not win her over with confidence. I didn't have any confidence. What I had was a massive dumpster truck full of courage. I dumped a Brinks truck of courage out there, and that's what I want you to think about. Don't not approach a woman because you're not confident enough. If you wait for confidence, it will never come. Waiting for confidence is like waiting for Godot or waiting for a funny Adam Sandler movie. It's never gonna happen. But if you decide to use courage, walk over to that woman, say something vulnerable and real and authentic, she may or may not like you, but you have just bought yourself confidence that you'll have tomorrow and next week and next year. Think of courage as the currency that buys you confidence. Okay. Next, here's a big myth about flirting.You might think that it's hard to flirt. It's really hard to know what to say and how to flirt, but it's not. It's so much easier than you might think. I'd like you to use this analogy or use this image. Think of an EKG. And an EKG, you know, you have that baseline, middle line, And then you have these little spikes that go up or down. And think of flirting like an EKG line. And that middle line can be thought of as sincere, authentic conversation or communication.In other words, just being normal. Just talking about your life, yourself, and, sharing information, sharing information, sharing your viewpoint, sharing your personality, your sense of humor. And think of, think of 80 to 90% of your conversation with a woman on a first date or an approach or, for that matter, when you're texting on an app, 80 to 90% of it can just be that middle line. Just sincere. Just be authentic and sincere. In other words, saying what you're thinking and feeling, what's genuine and real. And then the flirting part of this is the spikes, the positive up spike and the negative, quote unquote, down spike. Positive up spike would be something like, hey, you're really cute, or you're adorable, or I love how confident and silly and fun you are, or, yeah.Wow. You have great taste in movies. So those are positive spikes, such as compliments. And then every so often, you can do what's called a negative spike. Not a nag. Not a pickup artist nag, but a negative spike where you might tease her. You might crack a joke about what a dork she is. You might basically show a little bit of, not negativity per se, but you're willing to have a full range of expression, up and down.

So the moment I want you to have is to be on a date talking to a woman just knowing, oh, I can be sincere. I can just speak normal thoughts, be sincere, be able to share about myself and ask about her. And then as long as you give her the occasional, just the occasional, 10%, positive spikes and negative spikes, you're gonna be flirting. You're gonna be giving her what she wants. Don't think that every other word out of your mouth has to be some amazing, weighty, awesome, funny, flirty, naggy line. It doesn't. 80 to 90% of what you say can just be you being sincere and authentic. And then give her some positive spikes.Give her some fun negative spikes. And guess what? You just got instantly good at flirting. It can be that simple. Gotta practice it. Don't get me wrong. You gotta practice it, but it can absolutely be that simple. Okay. Let's do one more. Here's a good one. I I want to talk about the power of playfulness. A lot of guys think, oh gosh, Connell, I don't know what to say. I don't know how to say it. I don't know how to text women. What do I text? What do I text? One of the biggest myths of how to text women is you've got to say witty, witty, amazingly creative things, good content, in other words. You don't have to. You just want to play with her.Just think playful. If some of your text messages are playful, then she's going to enjoy you. So you don't have to be clever. You do want to be fun and playful. In fact, I'm just thinking right now, live on air. Is this the single most powerful tool in your dating toolbox? It might be right up there. Playfulness and fun. Very few women.I don't know. I shouldn't say no women want to play with you, but man, I would say 98% of single women would love to meet a fun, playful guy who's got some good, fun, playful things to bring to the table. So how can we play? Couple simple strategies here. On dates or online, you can play games, like 2 truths and a lie. You can play, you can do thumb wrestling. You can play guessing games. You meet a woman out at a bar. She says, what do you do? You say, what do you think I do? Look at me. Look at my clothes. What would you guess I do for a living? Challenge her, but not in a dickish way. You're challenging her to play with you. You're basically saying, hey, let's play together. That's fun. It's different. I love staring contests on dates. I've played 1,000,000 staring contests. I like to thumb wrestle. I mentioned that, I do a game called the question game. We just take turns asking each other questions, and, the only the only rule is they you have to tell the truth. You have to tell the truth. So playfulness is not something that you need a lot of amazing, perfect for. Don't get me wrong. Being clever and witty is a nice bonus if you have that in your quote unquote game, but it's not required. There really isn't. So think of different ways you can be playful. And then the nice thing is you can be playful the same ways both online when you're texting but also in person. I was texting a woman recently for my YouTube channel showing guys how to do the art of getting phone numbers and dates, and I was just playing 2 truths and a lie with her, which is exactly what I used to do on dates. So find 3 or 4 simple ways that you can be playful, and you can do them both on dates. And for the most part, you can do them when you're texting as well. Okay. Let's do one more. Let's do one more myth I would like to bust for you. Maybe the biggest, one of the most prevalent myths in dating. I think one of the most prevalent myths in dating is that you have to be really good looking to get a woman attracted to you. You have to have Brad Pitt looks, male model looks, tall, ripped, perfect jaw. And you might think that's true, but the bottom line is it's not true. It's a nice bonus if you're good looking. Don't get me wrong. It's a nice bonus, but being good looking, it's kind of like owning a Jacuzzi. Good looks are nice to have, but overrated women get bored with it after a while. My girlfriend, Jess, she's not with me because I'm a male model. She's relatively attracted to my gingerness, I guess. I must be her type, but she's not with me because of my looks. She selects certain parts of my body that she's attracted to. She likes my arms. I have fairly nice arms, but, I don't have I don't have a 6 pack. I don't have low body fat. I don't have big muscles. I don't have the kind of face that makes women fan themselves as I walk down the street. So I've got to do it with other other assets. And that's the truth here. The truth is that women are different, women have a different blueprint for what they find compelling and magnetic to a man, and looks are much lower on the lists of most women than you think it is. Looks are much less important to women than you probably think. What's probably happening is you are projecting onto women the way we as men tend to feel, which is we're very visual. Men look at a beautiful woman and say, swipe right. Yes. I will date her. I will marry her just because she's so physically attractive. So physical attractiveness for attractiveness for men, it's kinda like a light switch. It turns on, especially if she's physically attracted to you. For women, attraction's more like a dimmer switch. It's something that gets turned up, and it's not from looks. It's more from confidence, presence, to an extent charisma, but not one size fits all charisma, your charisma. And, essentially, it comes down to the value that you can bring to her life.So I have dated I'm I'm not trying to brag when I say this. It's just the truth. I've dated women who are way, way, way, way more attractive than I should be able to date, models, model caliber women, and they have not chosen me because of my looks. They chose me because I had something to offer. I brought something to their table. Personality, a sense of connection, emotional connection, laughter, fun, playfulness. Basically, I brought a lot to her dating table. So please unplug from the bullshit story that if you are not conventionally great looking, you cannot get a quality wonderful woman in your life. That is not true. I've seen it too many times firsthand. Some of my coaches back in the day were not good looking men. They did it with swagger, with confidence, with a good, quote, unquote game. What I've seen that works best for me is authentic authenticity, confidence in yourself, and understanding how to make women smile. If you get how to make a girl smile and feel good about you by making her feel those good emotions, then you could look like Brad Garrett and she'll think you're Brad Pitt because you made her feel so good. Alright. That's it for today's episode.


Until next time, and remember, your dream girlfriend. She's out there. She already likes you. She just has to meet the real, authentic you. Adios.

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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

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NYC Dating Coach Connell Barrett

106 W 32nd St, New York, NY 10001

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