
Robbie was once so anxious around women he couldn’t even say hi to his crush, the cute cashier. And the idea of approaching women felt impossible. Then came one unforgettable Friday night. With dating coach and author Connell Barrett as his wingman,...
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A
But when you can walk up to a woman and be yourself and say, hey, what's up? I'm Robby, I want to meet you. What do you think of my style? You don't have to, you're not, you don't have to be stuck on the dating apps. The world becomes your dating app. Welcome back to the how to Get a Girlfriend podcast. I'm your host, dating coach Connell Barrett, here to help you get a great girlfriend and to do it by, by knowing exactly what to say and flirting like you mean it. And I have a really special guest today because joining me is Robbie. Robbie is a former client of mine who now has a girlfriend and he has absolutely crushed it with me and he is going to share some of his approaching and flirting struggles he used to have and then talk about some of the breakthroughs that he had, including one of the most amazing nights I've ever seen a client of mine have. Welcome to the podcast, Robbie.
B
Thank you very much for having me.
A
Thanks for being here, man. I cannot tell you how inspiring you are to other people. So you first came to me way back last year and you were struggling. As I recall, you were dealing with some things like social anxiety and you just wanted to be able to meet women out in the real world, flirt, chat, get some dates, tell us about where you were when you first spoke with me, 100%.
B
So I think I'll basically go on a tangent about my life, how I always dealt with low self esteem, how that pretty much, pretty much I wouldn't, wouldn't want to say ruined my teenage life, but impacted in a really bad way. So I'm the kind of kid who always dealt with really bad low self esteem. I never thought of someone who's good looking or is deserving. On top of that, I always had like social anxiety. So not just dating, even in terms of just talking to people, I always struggled with that. So basically if you had social anxiety and also low self esteem, whether it's your social life or your dating life, both is going to be heavily impacted. And that's what happened to me when I was in my teens also. It kind of translated over to my adulthood as well. So I, I think till I was of a certain age, I'm, I'm in my early 20s, but let's say till I was 22 or 21ish, I always struggled to talk to anyone, just not in terms of dating, but just making friends in general. And I always felt that why would anyone want to talk to me? I'm not Smart. I'm not someone interesting. I don't really have any value to offer. So I really had to work on myself in terms of self confidence and stuff. That's when, when I was, when I turned 21, I had to work with a therapist who helped me, who with whom I shared pretty much everything about my life in terms of the low self esteem phase, confidence and stuff. And that's when she started helping me out. Rebuilding my low self esteem. Rebuilding my confidence and self esteem. Around the same time I was introduced to this book called Law of Attraction. Okay. And it kind of talks about how if you believe in something, you are really close to turning that into a reality. And that was a really life changing moment to me, coupled with the therapy I was going through. And that's when I really started to, let's say, rebuild my image or my confidence that I have in my own mind. I was the kind of person who. I wouldn't respect myself that much.
A
May I jump in, Robby, and ask you a question?
B
Go ahead.
A
Because self doubt is the big bad wolf of men who struggle with dating. Feeling like they're missing something, they're not valuable, they're not worth something. Not tall enough, not good looking enough, not charismatic, not something enough. What was the thing you doubted about yourself?
B
That's a really good point. You bring up. So pretty much everything. I'll just go into the details. My hide was definitely of the things I was insecure off.
A
How tall are you?
B
I am about five, eight.
A
Okay.
B
I, in my teen years, I used to have buck teeth. So that's something I really struggled with. I didn't get braces until I was 21. Okay. Then I was losing hair when I was 19. I'm. I'm under some medication, so now my hair is in okay condition. But there was a time when I would say I was literally half bald. So I wasn't really happy with how I looked in the mirror. I wasn't in the best physical condition as well. I wouldn't like what I would see in the mirror.
A
Right. Okay. And so when your mind is focused on not tall enough, don't have the hair, what do my teeth look like? It's hard to have the confidence to go socialize with people, let alone go approach a beautiful woman.
B
Right, exactly. Totally agree.
A
Yeah. So yeah, I didn't mean to jump in, but like a lot of guys say, Connell, what do you say? What do I say when I approach a woman? And I've got all the best flirty moves in the world, but if they're not. If those flirtatious lines aren't coming from a guy who believes in himself and knows he's the shit, how well is it going to work? Right.
B
Exactly right. So I was at a position where I didn't have respect for myself in the sense that I wouldn't think I'm deserving of anything. And that's when my, my therapist came in to help me and she would emphasize on the importance of self respect, self confidence. And that's when along with the book I was reading, Law of Attraction kind of changed my viewpoint on myself. And I strongly believe if you have a hard time respecting yourself, there's a high chance you're going to struggle respecting someone else as well.
A
Yeah.
B
So that's when I started working on my self confidence. But I still felt there was something missing and that's where Mr. Conor Barrett came into the picture.
A
Well, I coach my younger self and I saw so much of the younger me when you and I first spoke because I used to be racked with self doubt. You know my stories better than anybody. But the first night I ever went out to approach women first I had a panic attack in the bathroom because I was so afraid that, oh, women don't want some nerdy, shy, nice, funny, but not sexy, charismatic ginger to come talk to them. They want chads and alpha males and cool guys. So I'm literally puking in the bathroom because I was so nervous. That's what that fear self doubt basically turns an approach from a guy talking to a girl, which is all it is to, to judgment day on your worth as a man.
B
Right.
A
And I remember when you and I first talked because I do these consultation calls. Anybody can chat with me and tell me what's going on, see if I can help them. And you told me a story that resonated with me. Remind me if you would. Wasn't there a cashier who you had a crush on but you couldn't talk to her? How did you ask her out or, or show your interest? Tell that story if you would.
B
That's a pretty embarrassing story. But now I'm finding, I find it extremely funny now. And I think it's the embarrassing situations which really sets you free. And you can once you're okay with making a fool out of yourself in this world, that's when you're like free to literally do anything. I feel. And as much as I was embarrassed back then, now I kind of see it at some form of milestone. Probably not the best one, but yeah, it definitely had an impact in my life. So I. So I remember I was. During that time, I was still going through a really rough breakup and I was super depressed. And I would ask myself, why didn't my relationship work out? And right around that time, I. There's the supermarket close to my house. One day, one evening, I just go there and I find this extremely beautiful cashier. And the first thought in my mind I was like, you know what? I've had a rough breakup. And I think this is a sign from the world. Let me just go and ask her out, okay? And coupled with my depression, my low self esteem, I couldn't even look into her eyes. I was so freaked out. I. I just didn't have the courage at all. So I remember I went back, not being able to talk to her, beating myself up. And I was like, no, no, I have to come up with a strategy. I have to come up with something to finally ask her out. And I remember I had literally wrote a letter, like traditional, old school style. It was. I think I still have that letter somewhere. It's so embarrassing. I don't. I try not to look into it that much, but. But I still have it literally in my desk, which is right next to me right now.
A
What do you remember about anything that you wrote to her?
B
It was something like the moment I saw you, the beauty, everything. I was mesmerized by your looks and I couldn't stop thinking about you. And I want to take this moment to let you know that I am deeply in love with you. All sorts of stuff, all sorts of old school stuff that you can imagine
A
off to a woman you never talked
B
to, I never talked to.
A
And did you give it and tell us what happened next? Did you give her the note?
B
I tried probably four to five times. I would just go to the store, buy random BS for no reason just so that I could talk to this girl. And the only conversation we've had till now is, is. Hi. Do you need a bag?
A
Yeah, sure. Plaster her. And all she knows is paper or plastic.
B
Pretty much.
A
So did you ever give her the actual note or.
B
No. No. I could never have enough courage to go up to her and tell her that I liked her. And yeah, that's, that's, that's one of the stories, which I wouldn't call it an unfinished love story or whatever, but I'm kind of glad it happened because that's one of the times which really asked me, like, what's, what's wrong with me? Why can't I just go to anyone, approach Someone whom I like. And that's around the same time when I decided that, no, I need someone with experience to help me out.
A
Right. Well, it's an understandable question. What's wrong with me? Of course, the answer is, nothing is wrong with you. There is something a little bit funky with the way your, what I call the lower self, thinks about himself. Right. What's wrong with me? Oh, those stories of I'm not my teeth aren't good enough, I'm not tall enough. Why would she want me? That's the problem, not you. It's basically, you are a state of the art computer, but you had Windows 97 operating system. Look, look at me dating myself. Windows 97. But I had a similar story way before I ever got my dating life handled. I had a crush on a cute Starbucks barista at The Starbucks on 33rd street in Park Avenue here in New York City. And I wrote her a little love note on my business card at Golf Magazine at the time. And I, I walked up and I came, gave it to her, but I didn't say a word. And I. Not literally, but I felt like I ran out of the Starbucks. Like, here's, here's a note. And it said, you know, hi, I'm Connell. I come here all the time, and you're so pretty. And I wondered if you might want to go on a date, something like that. And shockingly, I never heard from her. What a, what a shock.
B
And perched right here.
A
Yeah. And so that's not the kind of communication that's going to get a woman's attention.
B
Right.
A
There's nothing wrong with taking a chance. It's how we do it.
B
Right.
A
And so you and I started working together. And do you remember the first approach you did while we were talking together? I don't mean that night out, but I know, I know you did some approaching before we went out for a fateful night that you had, which we're going to get to. But tell me about how approaching felt to you at first.
B
I still remember the approaches I did before the night out we did. And one of the things I remember, I think I was just walking down somewhere in Faidi, New York, and there's this beautiful lady. I think she was doing some sort of TikTok video or something. And I was like, you know what? I just want to go up to her and compliment her. I don't have to ask her out or anything. And even then, I was struggling with building up my courage and everything. And I remember I went up to her, I Couldn't even like lock in my eyes with her eyes. And I remember I was just like this. Hi, you look really pretty. I just wanted to let you know that I just left and I think she, she thanked me, but before she couldn't even reply, I just ran away from that, from there.
A
I wonder who is running faster, you from her or me from the cute Starbucks barista? Uh, we could have had a. A two, A two man foot race. But at least you did it. You started right, you took some kind of action. And did you find that it began to get a little bit easier? Because every approach, typically it gets at least 1 or 2% easier every time you do it. What was your feeling for the first half dozen or so? Any breakthrough moments, not counting our night out?
B
So what I realized is every approach ends up teaching you something. So from that moment specifically, I realized I wasn't making eye contact. And if I'm not making eye contact, sometimes even a person would be struggling to know if I'm really trying to talk to them. Am I really serious when I'm talking about literally anything?
A
Yeah.
B
Maybe there's a chance that that person just might not take me seriously if I'm not making eye contact,
A
Right?
B
Absolutely.
A
One of the biggest mistakes our minds make when we want to approach a woman is we look at it as win lose. Either I get her number and she likes me, or I failed and I'm unworthy and I should probably go marry a real doll or become a monk. You know, we look at approaching as win loss, and that's why it feels so high stakes. What? But you said something great. You looked at it as win learn. Right? Let's learn. Let's approach and learn a lesson from it. Better eye contact, louder voice. Try a different icebreaker. And that's a really smart way to do it. Because if we take approaching from a win loss to a win learn, then we stop associating so much pain to it. Start associating with, well, no matter what happens, I'm going to get value from this. I'm either going to get a cute girl's number, which would be amazing, or at least I'll learn something about myself or grow in some way 100%. Okay, so let's talk about an amazing night. It's one of the most incredible nights I've ever seen a client of mine have. Just explaining the background here. I do something about once a month called Fearless Friday, the night of 100 approaches, where a handful of my New York City guys or anybody who's In New York, who I'm coaching, we go out for a night and we try to as a group get to 100 total of approaches. I even brought up, bring a little ticker, a little clicker. You might remember that the guy who approaches the most girls tonight, I'll be his coach for life. I think that motivated you. So talk about that night. Talk about the beginning of the night. What happened that night. Tell us a little story about the night. Fearless Friday, what happened with you?
B
The viewers were in for a ride. It was, it was one of the, the most awesome, yet strange, in a good way, kind of a day for me. And I remember I had a photo shoot session the same day, right?
A
Online dating, right? Yes.
B
And I was talking to the photographer friend of mine. She's lovely, she's amazing. And we're just talking about dating in general, the kind of experience she's had and she has someone who's more experienced than me. How would she, how does she think about it and stuff. And I was sharing my insecurities and stuff with her because she's such a great friend and she was, I remember she was telling me, you know what, don't worry, I'm sure like you're gonna be one of the better looking guys out there today.
A
Okay?
B
And I was like, okay, that, that helps. Cut to you, myself and other clients actually meeting up.
A
Yeah, we're in the beer, we're in a beer garden, Houston street. Six or seven of us. Take it from there.
B
So literally every guy I saw just gave me a new sense of insecurity. Not gonna lie, I'm just keeping it as raw as I can.
A
How so?
B
So I, so somewhere I, I was really my pants that day because I've. It's, it's approaching night. It's, it can be scary. And as it was for me and somewhere, I don't know, I was just trying to justify myself being there. And one of the things I had in my mind was I just tried to be one of the better looking guys that night in that bar. Okay.
A
And for some reason, you mean your style or just how you felt?
B
I felt how I looked naturally as well. And every guy that came up that day, that night I felt was either taller than me, blue eyes, nice looking hair, better looking beard. Yeah, I feel I, I remember Taylor.
A
Remember Taylor? I think Taylor looks like Bradley Cooper.
B
I agree.
A
I, I'm a straight dude. I'm kind of into him. I mean this. We're going out tomorrow night. I hope we'll make out. Anyway, go ahead what were you saying?
B
So I was. I think there was like some. I think six or seven of us, right? Yeah. And there was a time when I was like, I have to be. I hope I'm just better looking than. I shouldn't think, like, this way, but I'm just keeping it as raw as I can. And I was like, I hope I can just be taller than one single guy out there, be better looking than one single guy there. And I was. I was literally shitting my pants every time someone new would come up. And I'm like, no, there's no way I'm doing anything tonight.
A
And then Ryan Gosling came up and joined us, and you were like, connell, come on, man, you're killing me.
B
That was literally my reaction. That's great.
A
You're tuning into something important. Because what we do when we go out to a bar to approach girls, we look around the room and we try to make sense of where do I fit in the.
B
The.
A
What's the word? Like the status of this bar. How confident can I be? Am I better looking than him? Am I taller than him? And that is what the lower self, that voice of self doubt does it with us. It is like pouring poison into our ears. And don't. We don't want to fight it. You just want to be aware of it. Like, there's this concept in Zen Buddhism called watching the thinker. Eckhart comes from Eckhart Tolle. I think it originates with Zen Buddhism. You watch the thoughts, but you don't get sucked into them. You're like, oh, I'm noticing how tall and attractive all these other guys are. Interesting. As opposed to going, oh, man, I'm just not attractive and as cool as all these other people. People. And then that hurts your emotions and confidence. And then you don't approach anybody. So, okay, you had your pre. Approach kind of nerves or moment of I'm not good looking enough, by the way, you are measurably H27 times handsomer than I am. I can say not even. And you actually have muscles, unlike me. But okay, so you're in your head, you're comparing yourself to all these other guys, and then it's the moment of truth. I say, all right, guys, night of 100 approaches. Fearless Friday. It starts now. And then it was time for everybody to start approaching. I did a quick approach. Just talked to a couple girls nearby. Nothing amazing happened. My girlfriend is with us, right. I'm approaching girls with my girlfriend there. But she's cool with it. She understands. And. And Then I. I got a couple approaches down. Then I'm like, okay, guys, now it's your turn. Do you remember what happened next with you and me?
B
I 100% remember.
A
Go on.
B
And I'm not sure if you recall the same event, but I'm just gonna say it. I don't know if you remember my first approach of the night.
A
I think I do, but you tell me.
B
And I. I mean, just making an assumption. I think that was probably one of the more, like, embarrassing situations. Just probably embarrassing only to me. But what happened, I remember was there was this group of girls, probably five or six of them, and they were, like, dancing to some song. They were, like, really vibing. I remember you coming up to me, and you're like, so you're gonna make your next move now? And I was like, yes. I see a group of girls, and I think I'm gonna go talk to them. And you're like, that's what I mean. That's right. Make your move. I tried my best to build up all the courage. And I remember I'm walking past them, and I lose all my confidence, all my courage. I didn't make any eye contact, and I just said randomly, hey, girls, I really love the way you guys are dancing. And no one looked at me. Except one girl. Even when she looked at me, she probably was thinking, like, who the hell is this guy?
A
Yeah.
B
And I was so embarrassed, I just kept walking. I just kept walking straight, acting like, oh, I have something important to do, someone's calling me, so I'm just gonna pick up this phone call on that side. But in truth, nothing like that happened. They just completely ignored me, I felt. Or maybe I just didn't approach the right way.
A
Was I there watching?
B
Okay, we're there.
A
So that I did notice. You do that, right? Remember what happened right before? Remember the deal I made? I told the guys the headlock approach or headlocks. Hold on. My cat is about to knock over. Okay, hold on. Say hi to YouTube. This is. This is Reggie. This is my little kitty, my little ginger boy. Anyway, okay, I don't. Don't want to knock this guitar over. So, as I recall, I make a deal with my clients. We go out to approach girls. I say, all you got to do tonight is take action, and you and I are going to be good. But if you don't take action, if you don't approach a girl when I want you to, I'll put you in a headlock, and I will walk over to you with you under my arm. And I will say to these ladies, excuse me, my friend, my, my buddy Robbie here wanted to approach you, but he was too big of a pussy. Say, hi, Robbie. So it's either approach like a man or get a headlock approach. I think you knew that and you just said, okay, it's time to start talking to women.
B
Exactly.
A
Oh, go ahead. I'll shut up.
B
I remember once I kept like walking straight and I was acting like I was on the phone with someone. You came up to me, you're like, what happened there?
A
And I was like ending the call.
B
Right. I was, I was so nervous at that point. But yeah, I didn't want to cut you off.
A
Well, this is a great lesson because the first approach of the night is always the hardest. You're in your head, you're not in the zone. You've been thinking about all this stuff. But I remember you doing maybe one or two more approaches. And then all of a sudden I saw you talking to two women who were seated at a bench. And you're, your body language looked different. You just looked really chill and relaxed. Tell us about the second and third approaches and specifically what started to happen about how you felt.
B
Great question. And just to give you some, a bit of context, I think it was Taylor or someone else who approached those two girls already. Okay. And I remember to myself, I was like, Taylor, such an amazing, such a good looking guy. And he already approached and I don't, I don't remember him getting the number. So I was like, there's no way I'm gonna get their number by any means. But you know what? I'll just shoot my shot. What's, I mean, what can really go wrong, right?
A
Yeah.
B
So I went up to them and in my mind I was like, instead of telling them straight up that, hey, you look really beautiful, I want you number or something, let me just start the conversation a slightly different way. So I went up to them and I was like, ladies, on a scale of 1 to 10, what do you think of my outfit? And I remember them taking my time, literally scanning top to bottom. Nice. And they, they tell. I think I remember, I think they told me. They gave me a 7 out of 10.
A
Not bad.
B
That's also another conversation opener. So I was like, why 7? Why not 10? What can I fit? Why don't you guys like it? You guys are just haters. So they, they were really genuine or at least nice enough with their explanation. And they were telling me, you could have added this to your outfit, this or that, but it was A really good conversation opener. And we were chatting for like a good five minutes about it, my outfit, their outfits. Then something came in my mind and I was like, you know what, if I guess your ethnic background in the next three attempts, you're gonna give me your number.
A
I didn't know this story. You became a game show host.
B
I literally was.
A
I literally was guess the ethnicity. I'm your host, Robbie, so keep talking. What happened next?
B
And guess what? I failed. I failed even on my fifth attempt. And I think I passed probably on my seventh or eighth. And I remember then they were like, you know what, I want to guess your ethnicity now. And they, they also took probably like five or six attempts, but they were right. And it was a funny game. I remember. And we talked for a good 10, 12 minutes and I kind of felt the conversation wasn't really going anywhere and I failed anyway, so I just told them, you know what, it was lovely talking to you guys. So I'll just.
A
You did so many things well there. The opener was great. I've, I've never seen. Hey, can I get your opinion on my style opener get rejected? I don't think I've ever seen that in all my years coaching men with approaching. That's a great go to opener. Hey, excuse me, but I like yours better. Not just what do you think of my outfit scale of 1 to 10. That makes her think. And a great approach strategy is make her an expert. We all like to be experts, right? You're a tech guy, right? I was going to ask you tech questions or finance tech questions. You probably feel like, oh, Connell, let me tell you what's up. Women love being asked what they think of a man's style, so great job. And then you turned it into a guess our ethnicity game, which is very playful because approaching dating. So much of it is about playfulness. That playful vibe is what women like.
B
And guess what? It doesn't end there.
A
Go on.
B
Right as when I was trying to leave, she stopped me and she said, so you're just gonna leave without asking me for my number? And I was like, now we're talking. And then she was telling me how she really appreciated and she found it really brave that I came up to her and talked to her and I was like, this is lovely. Just 10 minutes ago, I was living inside my head. I was like, this is the end of the world. No one's going to talk to me. I'm done. This amazing, this good looking guy, Taylor, he went up to them and I don't use the word rejected, but maybe he was, which is not a big deal, But I was like, if he gets rejected, there's no way I would ever get their number. And here I am. They are telling me how attractive they find me. They are telling me how brave of stuff that I'm doing. And I ended up with a number.
A
Yeah.
B
And she takes my phone. She also puts her name on it, and then she also puts the name of the bar in it. And she also says something. I forgot the exact line, but she made that assumption that I probably got a lot of curls. I probably do this all the time, and I'm, like, really popular out there or something. But are you saying she was trying
A
to make sure you remember which babe from your bevy of babes? She is? Exactly. Oh, that's so funny. Stacy. Houston bar, pink top. You know you remember me, right? What a stud.
B
And then I remember I hugged her. And then I came up to you guys, and I was like, I don't remember. You guys all are, like, cheering for me. It was. It was lovely.
A
I love that story because she told you something powerful women like a guy to come approach. It shows bravery. It shows this guy's got options. But he's talking to me. Think about the signals that sends. The very act of approaching a woman tells her, this guy's worthy of me. And, boy, did you find that out.
B
Yeah. I mean, I still. I would still remember the incident from time to time. But guess what? That was only the beginning of that night.
A
Right? Exactly. So that was your first number at Houston Hall. That's where we were. Right. Did you get any more numbers there?
B
I think I got a couple or three more at Houston Hall. Yes.
A
So, yeah. So you're crushing it. I'm with my girlfriend. I'm helping other guys who are not taking nearly as much action as you. That's okay. You were just in the zone. And how were you feeling at that point? After two or three numbers? How are you feeling about yourself?
B
So I still remember that moment. I think right before I made my first approach, I was constantly thinking, should I drink something before I go approach? So that it kind of, like, calms me down a little bit. And then something just told me, you know what? No, you. You gotta face this fear. And at that point, after that successful approach, I was thanking myself for not drinking or being under the influence of alcohol. And I was like, you know what this feels? I think this achievement feels way better than compared to if I was under the influence of any form of alcohol.
A
Yeah.
B
And I I had this high where I was like, I was on the top of the world. I could achieve anything. The book, the Law of Attraction. Everything is like my manifestation is coming into reality. That's what I was feeling like.
A
Well, that identity that you named yourself when we first spoke, supremely confident Robbie, you could feel that supreme confidence rise, right? And then we switched venues. We went to a different place. Place called the Broken Shaker. And that was really. When I saw you floating, you were, like 2ft off the rooftop there. You were just kind of floating around the bar, walking up to different women. There was such an assumption that this was going to go well. There was even a moment when it was Jess, my girlfriend. Myself and my personal trainer Zach came with us and a couple other clients. I said, everybody, watch Robbie. Look at him. This is what higher self in the zone looks like. And you approached. I think I even. It was the only time I told you to approach again, and you did it fearlessly. But I said, dude, look at those two women over there. And you just said, oh, I'll be right back, and went over to the two Dimes of the rooftop, other than my girlfriend, of course, the Two Dimes. And then they were. I don't know what happened, but they were just like, hi, and they loved you. And I don't know what happened there, but. And what were you. What was your highlight moment from the second spot?
B
So I think the first approach, it went for. I think I talked to the ladies for a good 20 to 30 minutes. That was. That was really fun. I remember it was probably a group of three or four people. And I remember. I think it was you, Jess, myself, and a couple of other guys. And I was telling you that, yeah, I'm kind of like scanning throughout the entire bar, like, whom to approach next. And you're like, why don't you start with them? And I was like, you know what? I will.
A
Nice.
B
I use the same opening line again. Hi, ladies. I don't want to waste your time. I don't know if I should have said that, but I did. Just want to let you know. And right to the point. On a scale of 1 to 10, what do you think of my outfit? And I remember all three or four of them walking on me, and they're, like, scanning top to bottom. And the girl that I really liked, who was in the middle, she was like, why don't you give us a spin? And I remember lending my hand to her, and I'm like, why don't you spin yourself? Spin me yourself. And she like, spin me 360. She was like, I could tell by her body language or like all the girls there they were finding extremely funny. And I remember she gave me some really good compliments. She also told me, I think it was another like a seven, seven and a half out of ten. I was asking her, why, what am I, what did I do wrong? How can I improve? And she was giving me some really good advice, actually. Some, some advices that I still follow till this date.
A
Amazing. Think about the guy you described earlier, the guy who couldn't even give a love note to the. The grocery store, the cute grocery store cashier is at two venues grabbing what, five, six phone numbers that night? How many?
B
Yeah, I think around that. 6 or 7. Ish.
A
6 or 7 phone numbers from cold approaching. And how many did you get any mean rejections the whole night or like distant, you know, get away?
B
No, no, not really.
A
Yeah. So you went from being that in your head guy who wouldn't even give that love note to the cashier to the guy who was grabbing six or seven phone numbers and just totally in the zone. If you can go, if you could give a piece of advice to the guy watching and listen or listening to this and say, here's what you need to do or say to have his breakthrough night out approaching, what advice would you give based on what you experienced that night and. And beyond?
B
The first thing I would recommend is to be comfortable in their own skin. Anyone who is going to ask out any girl, you know, you can cut that part out. I don't know what I was thinking, but yeah, start again. So, so great question. And the way I'm going to answer this is this. In my priority list, the number one thing is going to be self confidence, okay. And being comfortable in your own skin. Because if you're not as self, if you're not that confident in your own skin, somewhere you're going to feel that you're not deserving. And if you're not, if you don't feel that you're deserving, you're never gonna go and ask that girl out, Right? Somewhere you have to think of yourself highly and you have to think yourself in the sense that you have a lot of value to add to this world. You have a lot of value to add to the person you're going to approach to their life.
A
Exactly. And how do we do that? Every guy's got to find his own way. But I suggest to the listener, when you go out, tell yourself three things about yourself that you know Makes you a really great catch, whatever it is, and make them specific. You know, in your case it might be, I have a good job, I'm really good style. And you're great personality, great sense of humor, great personality, whatever it is that gives you a little bit of oomph. Because what this does is this takes your brain away from all that. Why am I not as good looking as him? Which is just going to drag your confidence down and makes you say, hey, what do I know? I offer, bottom line is women aren't looking at you and saying, why aren't you as good looking as that guy over there? Women are looking at you saying, okay, do you believe in yourself or not? That's pretty much all they're waiting for.
B
Makes sense to that point. It kind of reminded me of one other story that happened in that same republic approach. Okay, so as I was talking to all the girls, I think one of our dear friends also tried to like join us. And I forgot the gentleman's name, but I remember this tall guy, blue eyes, really good hair. And I was like, there goes my chance. Now all the girls are going to talk to him, they're going to forget about me. He comes into the picture with a girl that I was interested in. She just look at him once. And then she still maintained eye contact with me. She just didn't care. She was so fascinated by me and the questions I was asking and my wit. So just for anyone who's thinking, if they're not good looking, they're not enough. I mean, this is a great example.
A
That's a great moment of looks overrated, nice to have. If you're good looking, that's great, good on you. But you don't have to look like Brad Pitt, you know, if you look like Brad Garrett, you can still get somewhere as long as you believe in yourself. Here's why. Every beautiful, attractive woman has beautiful, attractive male friends. Gay friends, often. And these women aren't necessarily attracted to good looks. They're attracted to our presence, our personality, our ability to play, flirt, have fun with them. And more than anything, that core sense of your worth, that core confidence that comes from understanding your authentic value. So take it from a middle aged man who's, you know, I look like the lead singer from Weezer. I don't look like some male model. And back when I was single, I dated the most incredible women. They weren't hooking up with me because of my one pack abs. They liked my personality, they liked who I was. And the same goes for you. So yeah, good looks. Overrated.
B
Can. Can only go so far.
A
Yeah, that's nice if you have it, but overrated. Are there any. Look, I know you're in a relationship now. Can you share how you met your girlfriend? Did you meet her out in the real world? Was it an approach? Was it a social circle? How did you connect with your now girlfriend?
B
So I'm glad you bring that up. And yeah, it's. It's a pretty beautiful story. And she's, She's. She's amazing. And I met her through a friend. Basically, I have this group of friends that we're going to go for, like a random dinner one night, and she's basically a friend's friend, and she happened to come out the same night as well. And I remember, I think the first time we met, she was. She was a bit intimidated by me. That's what she tells me. And it has more to do with. According to her, I was so confident and I was there dictating the entire conversation, and she said, this is what she tells me now. But back then she would tell me, like, she was really intimidated by me, this and that. But now she tells me that she actually had a crush on me, but she, she wasn't willing to tell me at that time that she did. And that's something I've noticed with a lot of girls. They wouldn't. They. They wouldn't want to tell you straight up that they have a crush on you. They have their own way of delivering, letting you know at some point.
A
Yeah, they're more subtle, aren't they? Yeah. Women like to communicate in more subtle ways. Drop hints. Most women aren't very direct. Some are, but not too many. True. Not too many. And so for the guy who is thinking, okay, I want to go out and I want to get a couple phone numbers. Maybe five or six or seven, but at least one or two for a guy who wants to approach but he's afraid, or. Here's the thing, I hear more than anything else, Robbie, I don't know what to say. What do I say to that woman? What is your answer? What is your advice for the guy who is like, help us, Robbie. What do I say?
B
That's. That's a good one. And I. This is just my opinion, and that is just try not to sound too artificial, for lack of better words. Try to be authentic and trying to, like, use a topic that you can talk on for minutes or hours. For me, I love fashion. I love nice clothing. So that's why when I said or used A line. What do you think of my outfit? On a scale of 1 to 10, I know I knew exactly what I was talking about. I knew my stuff. And depending on whatever response they would have, I always knew a follow up question or things to add to it. So being authentic and probably picking a topic you love to talk about I think is probably one of the ways to go. But at the same time, you got to understand that not everyone's going to vibe with you or vibe with the things that you love all the time. And that's, that's how it is. We are all individuals. We all have our unique abilities or unique likings and everything. And if you approach 10 girls, probably five with five of them we're not even gonna vibe with. And that's fine. Just you're. And I think it's, it's for the better if you're not vibing with the person. Might be with the person. Be with someone that you have shared interests with.
A
Absolutely. You're not supposed to attract all of them. It's cold approaching. It's, it's like baseball. The best major league players in the world fail to get a base hit seven out of 10 times. If they get there three out of 10 times, and they do that for 20 straight years, run the hall of Fame, they're supposed to fail 70% of the time. And with approaching, that's actually a pretty close to good batting average. Once you get, once you get in the zone like that night on that fearless Friday, you got six or seven numbers. Do you remember about how many women you talk to?
B
I, I remember it was around the, around 25ish or something.
A
Okay. Yeah, there you go.
B
And I think I was lucky enough to get that many numbers because I, I would have been happy even if I got a couple of numbers out of the 25.
A
Yeah. So yeah, six or seven out of 25. So I'm bad at math. But you know what? One and it's like one in three more than.
B
Yeah, it's kind of like 30 or something.
A
Yeah. I talk about this in the, in my book the rule of one and four. My old coaches call it the rule of one in three. I think one in four is closer to accurate. One in four. When you are approaching, you get into a good zone and you're being really genuine and you, you know how to flirt, know what to say, within reason, but you just are in touch with that core worth. At a place like a bar, about one in four women will be pretty darn attracted to you. And that Gives you permission to not have three out of four be into you. You're allowed to not have them into you. We almost want to be so polarizingly, authentically raw and real that we're super attractive to women who like Connell's type or Robbie's type and then women who don't. That's cool. It only takes one to change your life as your girlfriend. Only takes a couple phone numbers to get into a really good zone.
B
Exactly.
A
The other thing. Oh, sorry. Go ahead, bro.
B
Yeah, I was gonna say that as long as you're putting in the reps, you're eventually are gonna get someone.
A
Yeah, yeah. You put in reps long before that night that were paid off that night.
B
Exactly.
A
Planted seeds that sprouted. And the other thing you did that night, I didn't even realize it until this conversation, but it sounds like you had, like, that back pocket opener you were using. Right. The style one. And that came out of an organic expression of what you were. What was on your mind that day? Right. You were getting new clothes with my stylist, Rianne. You were looking good or. Okay. And wanting to know what women thought of your new outfit. Right.
B
I think one of the things that helped me was Rhiann. She was really, like, complimenting my clothes. I. I would like to think she really liked my fashion, and somewhat that. That really helped me out in terms of. With my confidence. And this is what I've realized. If you can start off your day with just, like, one or two good compliments, it really sets up your day in a good way. Right. So that. That's what it kind of did for me. And I remember after the first couple of approaches, when it went wrong, I was like, okay, what is the one thing that happened to me was good? And I was thinking back to the time when Rihanna, she was giving me compliments about my clothing, and I was like, you know what? Let me make something out of that and use that as my opening line.
A
Yeah, I love it. I like how you were using what was in the ether. It was. It was just on your mind. And a lot of guys think, oh, I need to say the right thing. I need to say the perfect thing. Well, why don't you just share something that's on your mind right then and there, which is, hey, ladies, what do you think of my new outfit, scale of one to ten? Oh, my God, you could do that all night long. And I like that you had a back pocket opener. And that's another thing that helps if you. If you have a, Like, Break glass for approach. Opener in your back pocket. You'll have that to lean on if you need it. But then you probably won't even need it that much because you have it. So you can just be in the present moment. You know, women don't want to be approached by a robotic guy. Hey, ladies, have you ever walked up to a man? You know, that's just. That gets in the way. I was at the same venue we went to on a different night, and Jess was with me, and I left her to go work with another client. And this guy approached Jess, very pretty, my very pretty blonde girlfriend. And he came up and said, hey, I'm. I'm on a pirate treasure hunt. Will you help me find my lost treasure? And it was just like clearly something he had read on a Reddit for him or somebody told him to say. And she looked at him and said, awesome, sweetie, here's my boyfriend's business card.
B
I mean, she is badass.
A
She's an amazing wing woman. Okay, so you have gone from Ravi, the guy who could not give the cashier a little I like you note, to the guy who's grabbing six, seven phone numbers at a couple different venues. The lord of the club. What is your parting dating advice that the guy watching or listening to this, what should he go out and do in the next week to get him on the path to approaching success?
B
Great question. And I would have to go back to one of the same points that I mentioned. Back to self image again, confidence again. Once that is in place, I'm trying to think, what else can the person do? I would say fashion can also be a great point if you're well put together. No one, I mean, let me put it this way. If let's say you're not well put together, there's a high chance girls wouldn't want to talk to you versus if you are. Even if you're not the best looking, you still look presentable. And girls love that, right?
A
There's a poll I mentioned in my book. Women were asked, what are the five most attractive traits in a man who you meet for the first time in a dating context and looks good. Looking was not in the top five. Number two was looking good, meaning style. I think that was a men's health survey of women. Second most important thing women notices is this guy's style, right? Relatively well put together. You know, hair, grooming, clothes. So that's partially probably why you got into such a good zone that night is you looked good, you saw women respond to it, and yeah, Try not to dress like, you know, don't walk around vaping in sweatpants and flip flops. That's not going to help you. That's a little too authentic.
B
And I wasn't in any fancy clothes or suits or something. I think I had, like, a pretty basic black top, shorts, and white sneaks. That's it. And I was still getting. I think none of the girls gave me a rating less than 7 out of 10 that night. Okay. So you don't have to like.
A
And women will be blunt. Women will tell you if you're like, eh, four.
B
I remember, I think the last approach I did before I left, I don't think. I mean, I don't think they were necessarily being rude to me, but I think, like, some of them were, like, jokingly making fun of me. Yeah. I would give you a 2. And then, like, they just left. Like, they had a smile on their face and they were just, like, trying to be witty with me or something, from what I remember. But yeah, that. That's something. I agree with you. They're blunt. If they have something in their mind, they're gonna let you know.
A
To me, approaching is such a powerful thing to be able to do because we live in a world where everybody's on the apps, everybody's on social media. But when you can walk up to a woman and be yourself and say, hey, what's up? I'm Robby. I want to meet you. What do you think of my style? You don't have to. You're not. You don't have to be stuck on the dating apps. The world becomes your dating app. You know, you got six or seven numbers that one Friday night out, it's hard to get six or seven numbers on a dating app. You did it just by walking up to women, and so few men do it. And I think now is the best time to approach women ever, because guys just don't do it. And when that woman said to you, that was really brave. I'm glad you came up to me. Man, that said a mouthful.
B
Great. And the competition especially so low compared to, I'm assuming, what it was probably 20 years ago now. Right. Because pretty much every other guy is probably going with some form of or like a high level of anxiety. So it's like there's no one approaching at all. So it's for you. The only thing you need to do is just go and talk to the person you want. You want to talk to.
A
Yeah. I would say the number of single men who approach women would be at most 4 or 5%, even semi regularly. And most of those guys need liquid courage or some canned pickup line. Like the looking I'm a pirate looking for my treasure thing. The number of men who walk up vulnerably as their real authentic selves and just shoot their shot. 1% at most. So you are in the 1% club. Welcome to the club. Not that you need it.
B
Thank you very much.
A
Anyway, thank you so much for joining me today, Robbie, and thanks for being such an amazing client. And yeah, by the way, you listening? If you would like to go out and meet women, out with me and approach. Or maybe not with me, but if you're in New York City, we could do it together. If you want to go out and get 5, 6, 7 phone numbers in one night, I can't promise that, but if Robbie can do it, you probably can do it too. And just go to my website, datingtransformation.com you can book a free consultation to find out how my coaching works and if I'm the right coach for you. Or if you want to hire a coach to teach you how to write a creepy little love note to a Starbucks barista and creep her out, I can. I can do that for you too, for free. Anyway, go to datingtransformation.com and Robby, thanks for joining us and thank you for having me. Talk to you next time. All right. Adios.
B
Absolutely.
In this episode, dating coach Connell Barrett invites his former client, Robbie, to share his transformative journey from crippling social anxiety and low self-esteem to confidently approaching women in real-life settings. Robbie discusses his initial panic around social interactions, the steps he took to rebuild his self-image, and the major breakthrough during a live coaching event where he collected seven phone numbers in a single night. The conversation is candid, often humorous, and packed with actionable advice for any man feeling stuck in his dating life.
Struggles with low self-confidence and social anxiety since teenage years ([01:26])
"I always dealt with really bad low self-esteem. I never thought of someone who's good looking or is deserving. On top of that, I always had like social anxiety." — Robbie ([01:30])
Therapy and the Law of Attraction
Physical Insecurities
"I wasn't really happy with how I looked in the mirror. I wasn't in the best physical condition as well." — Robbie ([04:35])
"Self doubt is the big bad wolf of men who struggle with dating." — Connell ([04:04])
"We look at approaching as win-loss, and that's why it feels so high stakes...But you said something great. You looked at it as win-learn." — Connell ([14:56])
"Literally every guy I saw just gave me a new sense of insecurity...And I was literally shitting my pants every time someone new would come up." — Robbie ([17:42])
Uses a unique, authentic opener: “On a scale of 1 to 10, what do you think of my outfit?” ([25:28])
Turns it into a playful game: guessing ethnic backgrounds, playing off women’s responses ([26:57]).
Women reciprocate with positive feedback and numbers; one even prompts him to ask for her number ([28:30]).
Quote:
"She stopped me and she said, 'So you're just gonna leave without asking me for my number?' And I was like, now we're talking." — Robbie ([28:30])
Observes the positive contrast between his style of authentic interaction and that of more traditionally “good looking” guys—finding humor and success in genuine connection ([37:36]).
"She just didn't care. She was so fascinated by me and the questions I was asking and my wit." — Robbie ([37:36])
Collects 6–7 numbers over the course of the night ([34:56], [43:38]).
No harsh rejections—most women receptive or polite ([35:13]).
The core transformation:
"I had this high where I was like, I was on the top of the world. I could achieve anything." — Robbie ([31:46])
Skill development: Having a “back pocket opener” (style question) grounded in his own interests made him much more comfortable and authentic ([45:06]).
"If you have a 'break glass for approach' opener in your back pocket...you can just be in the present moment." ([46:20])
Most important factor is developing genuine self-respect and comfort in one’s own skin ([35:43]).
"Number one thing is going to be self confidence, okay. And being comfortable in your own skin." — Robbie ([35:43])
Connell:
"Women are looking at you saying, okay, do you believe in yourself or not? That's pretty much all they're waiting for." ([37:36])
"Style was the second most important thing women noticed. That's partially probably why you got into such a good zone that night." — Connell ([49:00])
"You're not supposed to attract all of them. It's cold approaching. It's, it's like baseball. The best major league players in the world fail to get a base hit seven out of 10 times..." — Connell ([43:01])
For more tips, coaching, or to book a consult with Connell Barrett, visit datingtransformation.com