
Do you fear that approaching women might get you labeled a creep—or even socially shunned? Connell’s client Ajay once felt that way. Drowning in toxic Reddit advice, Ajay believed that women didn’t want to meet good guys like him. In this episode of...
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A
Biggest piece of advice for guys is, like, if you're currently on Reddit, get off Reddit. Reddit. It's a terrible place.
B
Ajay, welcome to the pod, man. Thanks for being here.
A
Yeah, you're welcome. It's good to be here with you.
B
I like being a city boy, talking to a rugged, outdoorsy man like yourself. You know, if you and I should do like a body switching movie, like a Freaky Friday type thing where you end up in New York City and I am out in the great outdoors, hiking mountains and shit, I think that would be a huge hit.
A
I think that'd be really fun. I mean, I thought about it.
B
So Freaky Friday, it'd be Wacky Wednesday. Anyway, let's talk about some of the successes you've had working with me. And frankly, I'm just a coach. I'm only as good as my clients. I like to say to guys who I talk to, I'm not a wizard. I'm just a dating coach who's been doing this for 20 years. I'm only as good as my clients. And you've had some really awesome successes. I want to talk about. I like to start off with some of the issues that you were facing that first sent you to me that you were struggling with in the area of approaching women. Self confidence in those areas. So my first question is on our very first call where you said, hey, coach, I'm looking for somebody to help me. You said that you, quote, fear women and that you were afraid if something bad would happen. If you approach a woman, there's something to be afraid of. Can you unpack what you were afraid of, what that fear felt like and how you feel now?
A
Yeah. Okay. So, you know, it's funny, you sent me that question. I remember saying that. And so I can't fully remember what exactly I was afraid of. Having gotten to the opposite side of this. Okay, So I remember the main thing wasn't just necessarily about afraid of women specifically. It was like I was afraid of just people in general and them finding out, like, who I was. Like, I would say unironically, but it would sound like a joke. It's like, you know, I'm afraid of people finding out that I'm straight, you know, like, that I like women because maybe that was like a California thing or like a, you know, I went to a liberal college, lived in this very liberal feminist commune at the time, and it was not very cool to be straight. I was just afraid that, like, you know, if I were to make a romantic advance on a woman or, like, if they were to find out that I had any sexual feelings or thoughts at all, that those things were impure, like they were dirty, they were predatory, and that women did not want these things and that it would, like, ruin my moral character. Like, I had this obsession for most of my life of, like, you know, being a good person and being very, you know, stand up and moral. I was an eagle scout and all that stuff. Fought while I had fire in the forest service. And I didn't want that reputation, that image to be tarnished by, I don't know, people getting mad at me because I made a move on a woman and she didn't like it or something like that. Right, right. And in hindsight, I'm looking, thinking, like, I was way overblown, like, I was crazy and so were some of the people I was surrounded by at some points in my life. But, like, that was real for me. Like, when I started working with you, like, I was fully convinced that if my female friends knew, like, that I wanted a partner or that I just wanted, like, casual sex or something, that, you know, they would think less of me as a, as a person. So.
B
Yeah. I also remember you mentioning having this belief, this feeling about, oh, I don't want to get kicked out of society or shunned. Right. Do you remember talking about that with me early on?
A
Oh, yeah. Though, for sure. I mean, I still gotta catch myself on that one. Like, that fear never completely went away for me because it's such a deep part of my psyche. But, like, yeah, that was a huge one I was so afraid of. Like, what if I approach a woman at the store or at, you know, insert place here, and everybody sees because I get rejected. And then they're like, hey, man, like, some bouncer, like, white knight guy comes up and he's like, hey, that's not cool. You got to get out of here. Like, we respect women around these parts, right?
B
Doing something creepy and wrong by talking to a woman with romantic interest or even thinking about that. Right?
A
Pretty much. And the worst part is I was like, wait. But I respect women. And they're like, no, you don't. You just, like, went up to her. This is the drama that was playing out in my mind. Right, right.
B
No, it's very common. I think actually the most universal, the universal pushback that I hear from men is what, in terms of what keeps them from walking up and talking to a woman is I don't want to be a creep. I don't want to be bothering them or be seen as a creep. Be seen like I'm doing something wrong, because that leads to all these potential consequences in the mind, which in your case were things like, oh, I'll end up on what? TikTok will say I'm the world's biggest creep, or the security guy will kick me out. What was the catastrophe playing in your head?
A
You know what's funny? This whole time you're talking about TikTok. I've never used it. I never got into it on socials at all now. But, like, I was more afraid of. I guess Reddit was my drug of choice. I was afraid of being blown up on Reddit as one of those posts I would see because I would look to Reddit for relationship advice. So all this stuff I was internalizing was our relationships. And it was like, things like, you know, men of San Francisco, we need to be better. Like, you know, there was all these guys at the social event, like, trying to talk to girls and hit on them. And, like, you know, everyone was like, oh, my God, what's wrong with them? Why can't they just go there and be friendly?
B
Right?
A
And so something like that. I was. It was not just about the Internet, per se. It was more about real life, like, people that I knew in real life, or, like, being banned from, like, environments. And I had this totally irrational fear that, like. Like, the entire city would turn against me. You know, like, I would develop some reputation and some guy would see me somewhere else. Like, hey, you're that guy that creepily approaches women, right? Yeah.
B
That awful straight man who talks to the females to try to keep the species alive. What a weirdo. Well, talk about it, if you would. Let's talk about the flip side. It probably wasn't a specific moment or approach, or maybe it was. I don't want to lead the witness here. What shifted for you? What? Was there a moment or a sequence, a series of women you met or talked to or actions you took where you realized, hey, nothing bad's gonna happen. Some women wanna talk to me, some blow me off, and the society police are not gonna send me to Canada. When did you have that realization?
A
That's a good question. I mean, I think the improvement started a little bit small because, I mean, for the record, you know this already, right? But for the listeners, like, that fear never happened. I did so many, like, approaches, and not all of them went well. A lot of them went poor, poorly. They were awkward and stuff. I never got kicked out of society. Nobody cared. I doubt any of these people even Remember who I was. But even with that happening, I was on you and I were on the phone a lot about this, and I was just like, they're gonna know. Or like, I'm so scared. And you're like, but you haven't been, like, blown out yet. And I was like, oh, but it's gonna happen. You know, it wasn't until, like, week 12, right?
B
You didn't even have, like, bad rejections for a long time, right?
A
I don't think I ever had a bad rejection this whole time.
B
How many women did you talk to with me?
A
I don't remember.
B
Hundreds.
A
Not hundreds.
B
Dozens.
A
It wasn't as much as in college. It was, yeah, I'd say dozens at least. But after a while, it's like, the ones that don't go well, I just forgot about them because the ones that went really well, like, they went really well. So probably, like, the moment where it really clicked was when I went on that rafting trip. So I joined, like, a social club. And. Because one of the biggest things for me, too, if you remember this, was I told you in the beginning, I was like, my problem is that I don't know where to meet women. There's no women around where I live. And you said, that's not really a thing. And I was hesitant about the program because I was like, this guy lives in New York. He doesn't understand what it's like in Man Jose. Like in Sunnyvale, right? Man Jose. That's what they call it here. It's just a part of our collective thinking. If you ask my friends or just 10 people on the street here in my age bracket, what they think of dating in San Jose, and even the successful ones, they'll mention it. They'll be like, oh, yeah, it's harder because of the ratio. And even the guy, like, I know my friend who's really good with women, who just gets dates left and right. Even he, like, parrots this idea, right? So that was where I was coming from. So I joined the social club and to try to meet women because I realized once you started holding me accountable, I was like, I don't actually go out of my way to talk to that many women. Like, I'm not actually doing any approaching. I'm not too scared to go up to the women. I just see randomly because it's not a social context. And I'm not really aggressively putting myself in social context where I could meet women, right? And when I'd be in those situations, I'd be too afraid to express interest So I went on this trip, this drafting trip, armed with. This was week three, man to woman communication. So I just watched the module and I was like, this seems like bullshit. I don't know if this actually works. And it worked. Like, it just. It was life changing. It was crazy how I just. From the moment I got out of the car, I saw two women next to me. This was the Russian river in Sonoma county in California on a weekend. So there's, like, hundreds of people here, and all of them are here for the same reason, to float rubber inner tubes down this river. And, you know, it's like a big party, like a booze cruise type thing. And so I was here to meet this random club of people that I'd never met before, to do this with a group. And these two gorgeous women are next to me when we're getting changed into our swimsuits. And so I was like, all right. Connell said, I gotta approach six women. So here we go. And so I just talked to the first woman was like, hey, you know, I forgot. I said, but, like, I just think you're super gorgeous and I wanted to come meet you. And she and her friend, like, were not against it. They were appreciative, if uninterested. And the whole day went like that. Like, that whole day was the aha moment where every single group of women that I went to and just opened in the most direct way possible, just saying what I actually wanted to say instead of trying to make it work or be perfect. They liked it. They were, like, beaming. Like, they. All the groups, they told me, like, wow, thank you for coming up, you know. And the day later ended with me, like, I was talking to this one woman that was in our group that I had joined. And we ended up talking for no more than 10 minutes before I just had this moment of inspiration. And I pulled her in for a kiss, and she liked it. And this was in front of all of these, like, people. This was literally my nightmare, right? Like, I just. I didn't. I didn't just ask her on a date. I just kissed her, like, in front of the entire group.
B
The guy who's afraid of the society cops throwing him in prison is now making out with a girl he just met in front of all of her female friends. Talk about stepping up to your fear and, like, really changing the game. So what happened then?
A
Well, she liked it. She kissed me more. And then we spent the whole day together just, like, floating down this river and, like, holding hands and, like, flirting and talking about our Lives. It was really fun. It was like a life dream of mine to, like, have something like that happen, you know? And that day was crazy. Like, on a spiritual level, it changed my idea of what was possible in life and, like, what a human being, like a worth of a human being even was. What is.
B
What is the worth of a human being? What is your worth? What did you have? What was the realization?
A
Well, before I was like, you know, I was raised by immigrant parents, right? So that's where a lot of this dating stuff actually comes from, that everyone I knew had an arranged marriage when I was a kid, right? And none of these people were happy in their marriages. Like, they were forced to bury these people. And they would, like, justify staying by saying things like, you know, like, it's not that good. All relationships take work. Like, this is about as good as it gets, basically, right? Like, you can't really expect anything better than, like, working your ass off. And, like, there's a limit on what we deserve. Like, we can't have things that are too good to be true. And I lumped this kind of thing into that. Like, I lumped an attractive partner or woman or, like, hookups or all this stuff that I thought was, quote, haram, you know, like, forbidden into this category. And so when all this stuff started happening, I was like, holy shit, God is weirdly sex positive. You know? Like, that was what it was. I was like, I didn't realize God cared. Like, I thought I have to be running away and hiding, like, my sex life from the Almighty God.
B
Like, sex too. Hey, how do you think we got Jesus?
A
I mean, it makes. It's so stupid when you say it out loud because I was like, india has like a billion people there. I mean, it's not like they got delivered by the stork. So.
B
Yeah, And I love how in one moment you're kissing this cute girl in the rafting setting and you have. What I love is that you are directly at this time walking into the thing that used to scare the shit out of you. You're like a lion tamer, saying, time to get into the lion's den and. And realizing, oh, wait, nothing bad happened. There's no lions that are going to come and eat me. In fact, maybe there's just no lions at all.
A
It's still a weird concept to wrap my brain around, even now when I go to events. Recently I went to a tantra class that I was really interested in that a friend invited me to, and I met a woman there. We hit it off. I Asked her out. She said yes. We're seeing each other on Friday. And, you know, like, part of me is still in my head about, like, what if everybody saw? Like, I was afraid that I was gonna get some sort of phone call from the leader of the teacher because they'd asked me to come volunteer for them. That's why I was at this thing, right? And not that it happened. The text I got was like, hey, yeah, we thought you were really cool. Like, you want to, like, do a trial period of volunteering and then, like, you know, you'll just be a part of our team. And nobody cared. Dude, it was crazy. Like, it's so weird to wrap my brain around that, so.
B
Well, it's about doing. It's about taking the right action in the right measure. If you approached a woman and she wasn't interested, and I know you would never do this, but if you then approached her five more times and harassed her and called her names and didn't look at the woman's social cues, that guy's in fucking trouble. And he should be. But what you're doing is, hey, I'm going to shoot a little shot at romance here. If she likes it, you got your consent to keep going. And if she doesn't, you're a gentleman. And you'd be like, hey, all good, Nice meeting you. I'll let you get back to whatever. There's nothing to fear, within reason. As long as you're going through the world as a gentleman, as a guy who's aware of how women are feeling and adjusting accordingly, which is all we wanted to give people in life and give women is a sense of, oh, let me be present. Let me calibrate, make sure you're comfortable. Comfortable. If she's. If she's comfortable with you, then you're good. And if she feels uncomfortable, you can say, hey, you know what? I'll let you go. And then live to fight another day. But, yeah, I love that you had to. I love that you discovered this because you stepped into the thing you were afraid of and just said, yeah, courage, baby. Yeah. Now the listeners like, what did you say? How did you kiss her? What did you say to get all the girls into you? How did you spark attraction? What is your answer to that?
A
So in that moment. Well, one, the module, three missions, you had, like, a video about this. It was publicly available on YouTube. The man to women communication. That stuff works. It's not, like, specific things to say, but more like a way of being that is aggressively or unapologetically not aggressively straight. And as far as what I said to the girl at the rafting thing, actually, here's what I did. You'll love this. This is why I thought that God was sex positive. It's like I was talking to this woman and I could tell I liked her and that she was really, I mean, gorgeous, you know, And I was like. I had this realization in that moment where I was like, we're just having a friendly conversation right now, and I'm scared to make a move. I'm thinking about what's the right way to do it, right? What's the way to do it? That's not going to get me judged by anybody, and that's going to work. And I was like, if I continue down this path, this is gonna end like every other woman interaction I've ever had, except for, you know, a couple. But with the friend zone, right? It's gonna end with us just partying and never seeing each other again. It'll just be so boring and, like, mild, right? And I was like, I'm gonna have to take a risk, but I didn't know what. So I prayed, actually. I, like, said a little prayer to my higher power and was like, hey, like, take the wheel. Like, I don't know, my own best interest. Like, help me out here. And that was when it just came to me. Like, she had this really cute chain around her neck, and the chain had a loose end here. Like, it came down the middle. So I, like, picked up the chain and I, like, gently pulled her in with it. And then we, like, kissed each other. It was wild. Like, in hindsight, I'm telling this story and I'm like, that's crazy. So it's the sort of thing you would think wouldn't work and would be considered sexual harassment. But, like, in this case, it did, I think, because I went really slow. We had already been having a conversation. And I also, I got more clear through doing work in 12 step programs where my part in things was like, a lot of this fear about women had to do with, like, my upbringing, right? Like, my mom was. It was. It was a bad household. So, like, you know, she tried her best to hold everything together. But part of that was like, I, as her oldest son, was somewhat responsible for managing her emotions, right? And she was really afraid of, like, people outside the house, like, thinking that we were not the perfect Indian family, right? And so if I. If like, she got upset or scared for something, it wasn't like, oh, my God, I feel scared and upset right now. It was like, how could you do that? Like, you did this thing that was wrong, and you're bad. And the fact that I'm upset is a reflection of that. So I learned from a really early age to caretake women's feelings and that women were not to be held responsible for their own boundaries or, like, for stuff like that. And that was echoed where in college, I had that experience with women where I think a lot of my friends, like, had a hard time saying no and didn't really want to admit it because they were scared of judgment, just like all of us, you know? And so I kept getting these messages that I would focus on because it matched my already existing core belief. So in that moment, after having all that work, I was able to look at the situation differently, and I was like, look, I'm gonna go for this kiss. She's a big girl. If she doesn't want it, she's gonna say no or push me away or say, get the hell away from me, motherfucker. That's cool with me, you know? And that's the kind of people I want to be around anyway. Or, like, people that I don't have to caretake, like, who can take care of themselves, say no to me, you know? Yeah.
B
Nice. And what. What makes all of this work, other than authenticity, which I preach a lot, is just having empathy and noticing how a woman feels with you actually reading her body language. Is she smiling or is she frowning? Is she making it easy for you to go kiss her? Or is her body language all turned away? So we have to. And I know you do this, but we have to be really present to how a woman is feeling or to the best of our ability, because that's telling you what you can or cannot do or what you might try. And it makes it easier to take some social risks and go for that first kiss. If she's looking at you and her eyes are really big and she's licking her lips, hey, that might be a signal. And if she's not, maybe don't go for the kiss. So what I love about you is, is what was holding you back before, in part, was almost like you were being too safe in saying, oh, I'm not getting a sign held up saying, come and approach me, Ajay. Right? That was a little too much safety you were looking for, but you're now like, hey, I'm still reading women. I'm still noticing how they feel. But also, there are times when a man has to make a move, and that's part of dating yeah, that was.
A
A totally new concept for me. And that was. What's helpful about this whole experience, is that you were an experience of, like, a sane man who, like, was very, you know, mature and grounded in reality. So I think your takes on things were just fundamentally different than a lot of the feedback I was getting from my social circle before. And again, like, it's more used to it now, but there was definitely that period of, like, taking the red pill. I'm not going to use that. Oh, my God. That has a terrible association in this context. You know, like the Matrix, like, waking up and realizing, like, oh, my God, like, the sky is blue. What's up with that?
B
Well, now that. Now that you have all of these past, recent and current experiences, all these approaches, quick, fun, sexy makeouts, good dates, some love has happened, I'm told. And I know you're not right now yet with your final girlfriend, whoever she ends up being one day. But you've learned. You've taken so much of your own action. Here's my next question. Of all the things that you hear other people having told you, things you read on Reddit, or things your other people have said to you, what's the biggest myth you now know is bullshit? What's the biggest thing you're like, oh, those guys are wrong. Ignore that.
A
You know, this came to me in the last thing we're just talking about. I don't know if it's the biggest, but one that's really relevant here is I had this idea that, like, with the whole thing with, you know, being around people that had a hard time saying no, it was like, I had this idea that if a woman really wanted it, like, that she would be holding up the sign. I mean, that's an exaggeration, but basically, I was expecting women to, like, make the first move or to make it really easy for me, or that, like, I would see other guys successfully flirting and take that as evidence of, like, no woman has ever actually wanted me, you know, except maybe. But here's the thing, Connell. Like, the evidence I had for this in my life is I had, like, let's say, two women who did make the first move with me, who did make it really easy. Like, I'd been hit on before in, like, a therapy waiting room once. It was really sweet, actually. She. I could tell she was nervous, but she came up and she was talking to me, and she, like, complimented my glasses and was like, oh, my God, you must be so smart. You have the smart guy glasses. And I was like, I got these for $4.99 on jenny.com. they're cheap guy glasses.
B
You're a smart investor. You're smart as money.
A
But, you know, so I thought, like, this is what I can look expect, right? Is I don't have power in dating because talking to women is creepy. They don't want it. They don't want men to come up to them. And what they want, if they wanted it, they would have it. Because I thought that women had so much more power than they actually do. Like, I thought that they were just these goddesses who had easy lives because they were so privileged and, like, could pretty much have whatever guy they wanted if they were willing to follow a simple workout plan. And this was all just my own resentments and projections and stuff is because I was so confused. I was like, I was on this elite wildland firefighting crew. Like, I'd been really successful my whole life. I've been really physically fit. I've had lots of friends, even female friends. I was like, what the hell is wrong with me? And that's a hard question, right? Because, like, I was like, I must be so undesirable somehow. Otherwise, women would be coming up to me. And that's the myth. Like, that just doesn't happen. It wasn't until you told me that you're like, dude, like, I dating coach Conan Barrett. I've been approached twice. And I was like, yeah. It recontextualized those experiences I had of like, wow, I must be so attractive that two whole women, like, by my mid-20s, have come up to me and made the first move.
B
I've been doing this 20 fricking years, bro. By this, I mean actively, intentionally working on my dating life. Yeah, 2005 was when I said, I'm out of this relationship. That wasn't working. We were both settling. Time to change the game. I believe I've been cold approached by two women in 20 years. Now, other women did show a lot of interest, but that was actually them reacting to my positive social cues. Like, I'm at a bar talking to people, being really lively, and Connell Barrett, my higher self. Then a woman might talk to me or might make it clear she wanted me to talk to her. I'm not counting those. I'm talking straight up random woman speaking me, speaking to me out of nowhere twice in 20 years. So, hey, some guys get approached maybe. Maybe they're better looking or cooler than me. But all I know is my own experience. And it sounds like you were taking what was happening to you before and Saying, oh, I guess what's wrong with me? I'm not enough. And of course, we know what that creates, that shitty lower self on all the self doubt.
A
Yeah, totally. So, yeah, I would say that myth is the biggest one. Like, there's a few in there. One was like, that, you know, a woman would come up to you if you were enough. Like, that's not true. I think women, they're just as messed up as us. I mean, that's a bad way to put it, but they're. They have their own peers. Flawed. Yeah.
B
Flawed people like we are. Yeah.
A
Yeah. And I never thought I'd ever find a woman that I could, like, relate to who, like, would have struggled in dating despite being attractive and successful. But that's not true either. I met a woman like that. I met all kinds of women. You know, that was the coolest part about doing this was, like, just developing, just, like getting to have more intimate conversations with a lot of women that I wouldn't normally have those kinds of conversations with. And it just changed my entire worldview. So I realized that I'm actually not behind. I'm not as behind as I thought I was because, one, I'm only 29. I'm gonna be 30 next month. Yeah. It just made. It gave me just, like a space to just breathe and be all like, okay, I don't need to chase hookups. I don't need to do all this, like, what is it that I actually want? And I realized it's like, I want to take my time and find just a steady girlfriend, you know?
B
Yeah. Well, you did something that I really admire. And I. I remember when I first started going to these seminars, like, 20 years ago, I heard some really sketchy stuff. I heard some things like guys standing on a stage, essentially the. This, this red pill, toxic women are to blame issues. One guy said, oh, you know, all 80% of women, the children they have, it's not with their partner, meaning all women are sluts. So basically what he was saying, and I don't feel like. And now. And I feel like you were opening these doors on Reddit or hearing, having all this stuff poured into your ears, like, oh, women are. Women are just whatever, shallow, or they're different than us, or they're the enemy, or, you know, you should feel shame. And what I love about what you did, whether you had worked with me or not, is you said, I think I can do better than that. I'm going to shut that out and try something different. And I just say, I just want to say I admire you for closing those doors. It's really beautiful.
A
Thanks, man. Yeah, that's the biggest piece of advice for guys is, like, if you're currently on Reddit, get off Reddit. Fuck Reddit. It's a terrible place. Even the parts of Reddit that claim to be virtuous, like, they're just as judgmental and shitty as, like, the parts that aren't.
B
Yeah, I have. I have peeked into the dark reaches of Reddit, and I am not a fan at all, at least in the dating space. But anyway, let me turn things over to you. I want you to play dating coach. Okay.
A
Okay.
B
This is now your podcast for a couple minutes.
A
What?
B
I don't mean you don't have to take total control, but give some dating advice, give some approaching tips. Anything that we worked on that you did, that especially worked well in terms of how you approach or flirting. Anything at all. Guys love to hear some practical tips. Any thoughts from the what worked for Ajay O?
A
That's a good question. I mean, it's easy for me to say hiring Connell Barrett.
B
No, no, no, no, no.
A
But I can't say that. Okay.
B
I was not teeing you up to say that. By the way. Go to datingtransformation.com to hire Con. Okay, back commercial.
A
So what would I actually do if I'm talking to myself, like, five months ago, wherever it was, like, here's what I would say to him is, it's hard to distill this down to, like, moves, honestly, because, like, that, I think, is beside the point. So I did, like, the RSD, like, the pickup stuff back in, like, 2016 when it was coming out. And simple pickup was pretty good back then, but there was something missing in that, like, even simple pickup, which was a lot more wholesome, a lot more, like, sane, I think, than what RSD and some of the other guys were doing. It was all these, like, technique things of, like, here's how you talk to women. But I never really got in touch with, like, why I was doing it and what was holding me back. And your program did a really good job. So I would say that, like, do a journaling exercise first. Like, pull out a pen and a paper and write out, like, a few things. Like, one. It's like, this was a really good one. A friend made me do this before I hired you. He said, like, I want you to pull out a pen and a paper and write all women off and just fill in the blank and, like, highlight anything that you think is really judgmental or like, potentially, like, untrue. And when I wrote this down, this isn't something I would say on air because I don't want to offend any female listeners, but I needed to do it. For me, like, a lot of it was really, really unkind, right? Because that's just where I was at at the time. And, you know, but when I wrote it, I started realizing contradictions because I had female friends, right? It's like, okay to all women except Kimberly and except for Jen, except for, like, you know, other people, like, are this way. And it started to make me realize that I was afraid of phantoms, you know? And then the other thing is, like, what else would I do? Just go out and talk to women? You know, I would say the biggest thing I did was letting go of perfectionism.
B
Nice.
A
A nice big breakthrough I had was, like, I went to the city, to San Francisco, because, you know, down here there is some truth to, like, it's harder to meet women in this, like, particular tech suburb that I live in because there's not a whole lot of opportunities for random social connection. Connection. And so I went to the city. I rode the train up. I was, like, walking around to do my homework, which was spend 90 minutes approaching women, right? And it didn't go so well at first, you know, And I started getting in my head about, like, when these women would give me, like, middling to kind of, oh, okay, like, kind of responses. I was like, did I do something wrong? Like, am I messing up? Am I creepy? Like, would an average guy, like, be able to do way better than that? Is what I was comparing myself to, was this idea of where I should be if I wanted to be an average, good person. Yeah, don't do that. That's my advice. It wasn't until I started riding my bike somewhere else to the city and processed that, and I realized, like, look, even if I really want to be, like, the perfect person, the reality is I'm not. Like, I have these very deep flaws, and I have this inexperience. And there's no shortcut here. The only way to keep from being the guy you described to would be in trouble, you know, like, who's not reading social cues? I wouldn't say. Like, for me, it wouldn't necessarily have been that I didn't want to is that, like, some people just can't. Like, they weren't taught how to, you know, and especially men. Like, we're not conditioned to be like that. And the only way out is to crack a few eggs, frankly. Like, Go somewhere where no one will recognize you again and like, make mistakes. Like, piss off a few people if you have to. Like, you're not doing it like intentionally, but if they want to get upset, like, let them be upset, you know, and that's easier to say that than to actually do it. Because I feel like shit when other people get upset. But like, unfortunately or for better or for worse, I think that's just a part of the journey that is required really to do anything.
B
Yeah. Let go of perfectionism. And the best approaches are imperfect. We want them to be committed. You want to. Here's something that hopefully resonates with you. I don't really care what you say to a woman. I want you to commit to that approach. Stand there like you belong there. Do your best. Let her hear your voice, let her look in your eyes, let her deal with you in the best intentioned way. And then the chips are going to fall somewhere. I just, I have a brand new client. I'll call his higher self. Name is Maverick, because he's a. He's a pilot. He loves Top Gun, his favorite movie.
A
Oh, cool.
B
Maverick. I'll call him Michael. He just did his first approach of his life Yesterday at age 44. Walks up to a woman and said, hi, how are you, Michael? She's like, hi. And she smiled and had a really great conversation with him and hi, how are you? There's no fancy game there. That's the most basic thing in the world. Hey, you commit to it. You smile, you own the space. And women are noticing all the sub communications that project your authentic core value you bring to people. As a man, maybe she'll be into him, maybe she won't. So I love imperfect openers. Like, I don't think I ever gave you this exercise, but I know I've given it to a couple other clients. So, dear listener, here's your approaching mission this week. Go up to five women this weekend. And if you're a guy who gets stuck in your head and you don't know what to say, walk up to a woman who you're very intrigued by. And walk up and say, hi, I don't know what to say to you. And then tell your name. Just own the imperfection of that. And you might be surprised at the vulnerability, but the vulnerability of that is what makes it so great. And the honesty. And you'll come up with something after that. I don't know what it'll be. So, yeah, perfectionism. Take it from a guy who tried too many times to have the Perfect, witty line. When I embraced imperfection, it got. It was more real, more relatable. And then paradoxically, my. My witty, funny self would come out because I wasn't trying so hard to be perfect.
A
Yeah. I mean, a large part of it just has to do with, like, feeling safe, you know?
B
Yeah.
A
I think when people feel safe, and because it is safe, we just don't always feel that way. And it's easy. That's what I mean with the breaking eggs. Like, it takes me, like, usually at least two or three, like, really awkward interactions before I get going and stuff just starts flowing naturally.
B
Yeah.
A
I also would say to the guys, like, man, the bar is so much lower than I thought it was. Like, I had this idea that we would have to measure up to some crazy standard because women had so many options. Because that's one of the stories people tell around here. Because we're all in tech, we're obsessed with Hinge. Right. And, like, statistics and stuff like that. And it's total bullshit. Like, the bar is so much lower. Like, I literally had a woman tell me on a first date, and she was like, I'm so glad you asked me out. Like, this is a great date. Like, I really need to get out of my house. And, you know, like, I forget exactly the way she worded it, but she told me that I was better than most of the guys on Hinge because I could, quote, tell a joke, and that was it. Because I could tell a joke. And there was some other really, like, basic thing. I was, like, laughing at her, like, oh, it's so great. Like, you're so good at compliments. Like, I can tell one joke.
B
You know, I don't mind a low bar. I can jump. Jump right over it. And I have a 2 inch vertical leap. But if I can jump over it, I'll take it.
A
No, exactly. And it was just really like, this moment of empathy where I was like, oh, yeah. Like, they want the same thing. They're trying to find Mr. Right, too. And it's like they don't.
B
They're just like, be normal. Just be normal. Be chill. Listen to me. Be a person.
A
You'd be surprised at how far they're not all out there expecting some Navy SEAL decathlete who went to Harvard and, like, is a standup comic. You know, that's not. That doesn't even exist.
B
Right.
A
So, yeah.
B
Awesome. I'll leave you the final word. Would you like to end with a tip or a moment that you went out there and achieved that really makes you Smile. Or any final parting words for the guy who's listening to this? The guy who's listening to this, he maybe he hasn't had a date in a long time. Maybe he wants to approach but he's afraid to. Maybe he just feels like women won't like me, I'm too brown, or I'm too short or I'm too fat or too something. What would you say to this guy besides Higher Connell? Besides that?
A
I think the one that really resonates is the I'm too brown or the I'm too. Insert ethnicity here. I had that too with you. Like, you like self deprecate jokes a lot on your content where it's like, oh, yeah, I'm a nerdy ginger, but I didn't see you that way. I was like, this guy's just pretending he's a fake self, you know? For people who don't know what that is, there's on the incel, dark corners of the web, they accuse people who they think are too attractive to be fake cells. Like, oh, you're not actually an incel. You just have low self esteem, you know? Okay, I'll spoil it. There's no such thing as a real. It's. You're all fake cells. I was. Wait, that's not really a thing.
B
Define fake cell again for those who don't know the term.
A
So, like, an incel is somebody who, like, well, this is what they believe, right? It's like, who's so ugly or like genetically, like ungifted that there's no hope in ever of them ever, like, getting what they want with the opposite sex, right? And the frustration is that, like, when people would come onto their site and say, like, let's say, oh, I'm an airline pilot and I'm struggling with women, I'm an incel. They'd be like, you can't be an incel. You're a fake cell. You know?
B
Okay.
A
Like, you're just not doing the work, right? And so I have a friend who teases me about this all the time. When I tell him my dating success, he's like, dude, you're a fake cell man. So that's what I would say is that there's no such thing as that. Like, I learned that. I mean, I do want to give big compassion to, like, there was a huge part of me that internalized so much racism growing up that, like, I genuinely did believe this. That like, because I'm brown, because I'm Indian, like, I'm not worth as much as other People, and especially in dating, like, I'm not going to get attention from women or if I do, it's not going to be because they're attracted to me. It's because I, I don't know, money or something. I don't actually have money. I'm an outdoor dirtbag. But you know, like, I thought it would be like something like that and it's just not true. Like, I realize other people are not thinking that way. Most people have never even heard of an incel like in their lives. Like most people don't. Are not as mean to me as I am to myself. And so I mean, that was my biggest takeaway is like, don't give up. Like, you're not broken.
B
Yeah. So your old belief was your, your heritage, is it Indian?
A
Yeah.
B
So you have Indian heritage. Your old belief was, oh, I'm not worth anything to women because I'm Indian in a fairly white country. Something like that, right?
A
Yes, exactly.
B
And what shift or changes did you see and feel and how you feel about yourself now relating to your race and attractiveness?
A
I guess I see myself as like, yeah, I'm a flawed person and I also have such self respect and offer myself because I know like the stuff I've crawled through through my life, you know.
B
Yeah.
A
And I also know that it's BS like women. And it was helpful getting a lot of positive feedback from a lot of women that I was really attracted to, you know?
B
Yeah.
A
Just. And it's not like that's just like a cure, I mean, but it's more that when that shame and stuff comes up, I know where it's coming from and I know how to deal with it. I don't take it at face value or believe it's lies. So. Yeah, right.
B
I think. Didn't I tell you on our first couple of calls that the very first coach I ever had in person is Indian?
A
Really?
B
Maybe it wasn't you. So I have quite a handful of Middle Eastern slash Indian heritage clients, so I must have told somebody else. But the first chapter of my book opens with this story about me approaching women first night ever. 38 years old. I'd never done it before. My coach was a guy who went by the name Ryan. It's not his real name. I won't give his real name. He's out of this world completely. But he went by Ryan at the time and Indian guy, American raised, but Indian heritage, very brown. And he even talked about this limiting belief he had about, oh, women won't want me because I'm this just a brown 5 foot 8 guy, right? And Ryan arguably was the best I ever saw in terms of approaching and just using wizard moves of just, like, being hypnotically attractive to a lot of women and to me. Not that my issue wasn't my skin color because I'm a white ginger dude, but I still have my own limiting beliefs. And I was like, wow, if he can break through that, then who knows what I can do? And so seeing a guy like you approach women of all different colors and shapes and sizes, I assume, and ethnicities, having. Having you have that realization feels great to me. Think about that's the thing about limiting beliefs is we can tell ourselves it's bullshit, but it's not until we get the hard evidence, the proof where we're like, oh, now I know it's nonsense, but that's why we have to go out and take action. Which you've done.
A
Yeah, it certainly helps. I mean, it's like that spiritual paradox of, like, yes, we could all just be the Buddha and, like, you know, just be totally enlightened. But it's way easier to do that if you have, like, certain things like food and water or, like, building self worth, you know, like, it's theoretically possible because it is unconditional. It has to be unconditional by nature. But the crutches do kind of help, like, having people that like me, like, say good things about me, stuff like that. Right? So, yeah.
B
Awesome. All right. Jay, you're the greatest, man. I wish I had so many more clients just like you. You do. The most important thing, if I boiled everything down to that I teach into one sentence, it would be take courageous, authentic action while respecting the women you talk to. And you've done that dozens of times, and look where you are now. And you know what? There's a lot of great things still to come, like whoever the one ends up being, or the next one in your case. So I'm here for you, okay, bro?
A
Thank you, Kahl. I appreciate it. Take it easy, man.
B
Thanks for being here. All right, that ends today's episode. Hope you enjoyed that. And again, not to market at you guys too much, but if you would like to have the kind of dating success that my man Ajay had, you can book a free call with me. Just go to datingtransformation.com and I'll get on the phone, I'll tell stupid jokes to you, and then I'll tell you how my coaching works, and we'll figure out if we want to work together. It's a free call, all right? Otherwise, keep listening. Thank you for letting me be your podcast dating coach. And until next time, later.
Date: October 14, 2025
Host: Connell Barrett
Guest: Ajay
This episode delves deep into Ajay’s transformation from socially anxious “nice guy” overwhelmed by fears and toxic Reddit advice to a confident man capable of genuine, romantic connection. Through candid storytelling, Ajay and Connell explore overcoming self-doubt, cultural barriers, and perfectionism, ultimately revealing practical strategies for authentic dating success. Ajay’s journey is both insightful and emotionally resonant, illustrating how vulnerability and presence—not “creepy pickup moves”—forge real bonds with women.
Notable Quote:
"I had this obsession for most of my life with being a good person...I didn’t want that image to be tarnished by, I don’t know, people getting mad at me because I made a move on a woman and she didn’t like it or something." – Ajay (02:58)
Notable Quote:
"That fear never happened…I did so many approaches. Not all of them went well...I never got kicked out of society. Nobody cared." – Ajay (06:57)
Notable Quote:
"That day was crazy. On a spiritual level, it changed my idea of what was possible in life and, like, what a human being, like, a worth of a human being even was." – Ajay (11:35)
Notable Quote:
"As long as you’re going through the world as a gentleman, as a guy who’s aware of how women are feeling and adjusting accordingly…there’s nothing to fear, within reason." – Connell (15:03)
Notable Quote:
"I thought that women had so much more power than they actually do...I must be so undesirable somehow. Otherwise, women would be coming up to me. And that’s the myth. That just doesn’t happen." – Ajay (23:36)
Notable Quote:
“The only way out is to crack a few eggs, frankly. Go somewhere where no one will recognize you and make mistakes…If they want to get upset, let them be upset.” – Ajay (32:26)
Notable Quote:
"There’s no such thing as that [being undateable for race/looks]...Most people are not as mean to me as I am to myself." – Ajay (39:41)
Notable Quote:
"I would say the biggest thing I did was letting go of perfectionism...the only way to keep from being the guy...who's not reading social cues is to make mistakes. That's just a part of the journey." – Ajay (31:12)
| Segment | Timestamp | |-----------------------------------------------|------------| | Ajay’s Reddit warning and initial fears | 00:00; 01:42–06:16 | | Fear of rejection and social consequences | 03:50–07:38 | | The transformative rafting trip story | 09:00–12:03 | | Spiritual “sex positivity” realization | 12:03–13:18 | | Respect, consent, and breaking perfectionism | 14:50–16:13, 31:12–33:10| | The myth of “women make the first move” | 22:26–25:51 | | Ajay’s advice for practical dating steps | 28:59–31:12 | | Debunking “I’m too brown/short/fat” self-talk| 37:37–40:33 |
Ajay’s journey is a testament to the power of authenticity, courage, and healthy self-reflection in dating. His transformation—from paralyzing fear and internalized shame to direct, wholehearted connection—offers a road map for “nice guys” everywhere: take social risks, own your quirks and imperfections, and trust that women actually do like “good guys” who show up as themselves.
“Take courageous, authentic action while respecting the women you talk to. And you’ve done that dozens of times—and look where you are now.”
— Connell Barrett (42:51)
Recommended for all listeners who want a relatable, actionable, and empathetic guide to authentic dating.