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How to Date in Your Social Circle—without Being “That Creepy Guy” (Live Coaching with A.J.)

65m 38s

How to Date in Your Social Circle—without Being “That Creepy Guy” (Live Coaching with A.J.)

In this podcast episode, dating coach Conno Barrett hosts AJ, a former client who has made significant progress in approaching women and securing dates. AJ recounts meeting a woman in a park by asking a simple question about a caterpillar, which led to a date plan that later fell through due to a scheduling conflict. He seeks advice on how to handle the situation without seeming pushy or losing her interest. Conno suggests using assumptive language when confirming dates, such as playful references to the planned activity, to avoid giving women an easy out. He also recommends rescheduling promptly after a cancellation to maintain momentum. AJ then raises concerns about dating within his social circles, like yoga and improv classes, where he fears being perceived as a creep or facing social backlash if he develops feelings for a friend. Conno validates these fears as signs of empathy but encourages AJ to move toward his desires with intelligent action, noting that worst-case scenarios rarely materialize. He advises that coffee meetups can be a low-pressure way to build chemistry and that having attractive female friends can be valuable. Ultimately, Conno urges AJ to stop letting hypothetical judgments from strangers dictate his behavior and instead focus on authentic connections.

Transcription

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Hey, Conno, is it weird and creepy to take a shot at love? No, that's what our job is. It's weird and creepy to not take no for an answer and follow her home and turn into Joe from you. Joe from you, he's gonna get in trouble on TikTok and read it. You're just a dude chatting up a cute girl in a yoga class. (upbeat music) Hey, welcome back to the How to Get a Girlfriend podcast. I'm your host, dating coach, an author, Conno Barrett. I am here to help you know what to say and flirt like you mean it and help you get a great girlfriend. And I'm really excited to welcome back to the podcast today, a former slash kind of current client, more former great guy named AJ. AJ worked with me last year and he came to me because at first he was really struggling with, "I want to approach women. I don't know how to flirt. I don't know how to make some moves without creeping women out." (laughs) And he had some approaching anxiety and he since has gone on to have some amazing breakthroughs, approaching women, getting dates, having some great stories. We might talk about some of these. And today he's got some more advanced dating questions to help take him to the next level. So anyway, welcome back to the How to Get a Girlfriend podcast, AJ. - Thank you, Carl. Oh yeah, thank you so much for having me. - Awesome, man. Well, let's just get right to it. What are some of the flirting or dating issues you're bumping up against? And how can I help you? Where would you like to start? - Yeah, well, actually right before this podcast, since I have you, I was gonna go on a date tonight. (laughs) I met this girl in the park, which thanks to the coaching and everything, it was really cool that I can just walk up to girls in parks now that I think are cute. - You didn't get arrested? Like for talking to another woman? - No, no, not this time, but like I made sure to clear the coast first, you know? And I got out of there before the cops could roll up. But no, it was insane. Like she was, I think so far, every girl that I've come up to in the park, only one girl was like clearly unhappy that I approached her, but I, you know, very quickly picked up on that and just left her alone. Did awkward, but nothing happened. And the others, even though most of them had boyfriends, they were happy that I was, that I came up to them. - Beautiful. - Which is really interesting. Yeah. And this girl in particular, like we hung out for a while, it was fun and like we, I saw her like looking at the dirt, you know, and I'm really outdoorsy. So like she caught my eye. I was like, what are you looking at? She had found a caterpillar. So we just hugged out and admired caterpillars and talked about ecology for a while. And then like we talked about yoga, she's a yoga instructor and asked her out, like you know, you want to go on a date. And she's like, yeah, sure, we're both new to town. And so I got her number. We started planning a date. And she just went up and up. - Can I jump on real quick? - Oh yeah. - Masky, so you're, first word you said to her, what are you looking at? - I don't think I phrased it exactly that way. I was like, hey, you know, what are you doing? (laughing) - It's that simple. It can be that simple, right? You saw her looking at dirt and you asked her where she was looking at. And now you're going to date with her. I just think it's good to mention that because so many guys think, okay, what's the perfect line? What's the fancy, cool, witty, amazing line? And you know what, hey, why are you looking at dirt can work or something close to it? - Yeah, and I mean, I've had success too, it's just being really direct if I can't think of anything to say and just tell the truth, which is, hey, I was just walking by, I thought you were totally adorable or something like that. And just like, what did it come say, hey, and then just gauge her reaction. Some girls are really open to talking, others will let me know right away that they're not interested. - Yeah. - Great, okay, so you did your patented catapillar dirt opener. Yes, you trademarked that you use all the time. No, you chatted her up in the park, you chatted and obviously set up a date. So yeah, catch me up. What's your question from, or catch me up, what would you like to know? - How do you follow up properly? 'Cause I'm in this awkward situation now that I've been in many times before, where we're just kind of struggling to, I guess, find a time to actually go out. And I'm starting to worry that she's just gonna lose interest. We were supposed to go hiking after work today, but at the last minute, she told me that last night she was out with some friends at a concert and they want tickets to a different show tonight, which is totally valid. It's subtrotics. I mean, I would go for free subtrotics tickets. So yeah, like she's not available and I wasn't sure how to handle it. I mean, I asked if she was down tomorrow 'cause the weather forecast improved, but I'm not sure at what point to just stop trying if it's like she's trying to ghost me or something like that. - How many days ago did you first meet her? This was Sunday. - All right, we're recording this on Friday, so it's been about five days. - Maybe it was Monday. - I don't remember, yeah, holy. - Four or five days. Here's my view. If you definitely wanna date with this woman, with any woman, keep in mind a couple of things. Seven to 10 days is typically how long a good first date lead will last before it goes cold. - Iron's always hot, so you always wanna ask a woman out sooner rather than later, which you've done, which is great. Now she said, oh, she had to change plans with you because of this other social event she decided to go to. And your question is, should you keep asking her out? - Yeah, I can't remember. - Yeah, 'cause I remember you cautioned me against like continuing to try to make plans. But you know, I'm in sales now. It's like, I'm pretty much going to follow up until something goes cold. (laughing) - I think that's smart. Here's my view. I think I know I said this to you when you were in the, you know, the couple months we were actively working together. With a given woman, you wanna go on a date with her. You assert what you want, which in this case would be a first date until you get it in a win-win way. Or until you get clear evidence that you won't get it. So clear evidence would be, A.J., I'm not interested. I just wanna look at dirt and not date you. Fine, that's clear evidence you can move on. But clear evidence wouldn't be, oh, you know, I need to reschedule. I'm gonna do something else tonight. That's where your sales training might be really helpful for you where you say, hey, let's just get an answer from this lead one way or another. And whether it's yes or no, that's totally cool in my book. But that's how you get the dates as you show that persistence in charm. - Gotcha. - Yeah, so what I would do is, you, by the way, the date you had, you had a date set up, did you say you had one tonight? And she canceled? Or you have one with her tonight? - No, no, no, no, like we were supposed to go hiking after work today, like at six or so. And yeah, and then like I followed up with her this morning just to confirm that we were still odd and then she let me know that her plans had changed. - Yeah. - How did you confirm, by the way, to remember what you texted, or can you tell me what you texted roughly? - I have it right here, actually. What did I say? - Morning, let me know if we are on for this evening. How was the show? 'Cause I don't, she said she went to a concert last night. - Okay, here's a preventative tip. Don't confirm a date the way you're confirming a business launch. - Okay. - Hey, are we still on for tonight? When you ask a woman, are we still on for tonight? You're opening the door up for her to go, oh, well you know what, maybe we can reschedule 'cause of XYZ reason. Don't wanna do that. It's okay, you do wanna confirm. You just wanna confirm in a more light, playful way that assumes that date is still on. So here's a good way to confirm. It's possible she might not have canceled on you. Had you confirmed in a more mild coach you should call it, a Sumpative Thinking. Let's assume the date is on and let her push back if it's not. So the wrong way to confirm a date is, hey, just confirming we're still on for tonight. - No good, that's probably great for your sales calls, but bad for states. Instead you wanna say, what was the date? It was hiking? - Yeah, yeah. - Cool. A great way to confirm would be, you know, day before or at the latest early the day of, you would text or something like, hey, you know, whatever Katie, whatever her name is, I'll call her Katie. Hey Katie, can't wait for the trail tonight. The views of the mountains are gonna be fantastic, you know, bring a canteen and bring some bugs, bring some caterpillars. (laughing) How, were you talk about the date? You can confirm that way. And if she writes back, oh my God, hello, that sounds awesome 'cause she doesn't want to cancel on you. She wants to be consistent with what she said she would do, but hey, maybe she wants to do this other thing. This, what was it, a concert? - Yeah, yeah, yeah. - Yeah, fair enough, I mean, it happens, she's allowed to change her mind. So we don't wanna open the door to that if we can help it, 'cause people, There's a really great book called Influence by a guy named Robert Chiel Dini. It's a famous book about persuasion and how to persuade people. You might know about it. And if you don't, it's really a great book. It's a classic book of human persuasion. He talks about this law of commitment and consistency. People just want to be consistent with what they say they're going to do. And when a woman agrees to a date, I don't like to open the door to her not going on the date. I don't want to make it easy for a woman, easier for a woman to flake than she already might want to make it. So that's one tip I have for you. Confirm the date in a different way. OK, cool. And if you can't find a funny way to confirm it, it can just be, oh, hey, is it cool if we meet 15 minutes later because I'm running a little bit behind? You could do it like that if you don't have something playful or fun. Because even because that's a really small ask. She still might have rescheduled. She still might have said, hey, AJ, you know what? This concert's coming up, but it's a little bit harder for her to do it without us giving her that opening. That makes sense. All right. OK, that's more of a preventative tip for next time. But you're are you asking so what did you next? Actually, I think you gave me kind of enough to work with here. So, OK, probably I'll keep following over there, but next time I keep it like you said, a bit more assumptive, a bit more playful. Yeah, cool. You don't end, you don't, how long was your interaction with her on Sunday or, what, sorry, Monday, whenever it was? How many minutes were you guys hanging out? Dude, how do I know? I did set a timer, but like it was kind of at least 10, 20 minutes. You didn't set a timer? Didn't I give you a clicker? Always record the number of minutes you talk to a woman. Oh, dude. Maybe there's an app for that that we can make that old. I just made a eye to do it. OK, cool. 10 to 20 minutes is plenty of time to be able to ask for the date, which you did. And then I guess what I'm saying is don't feel like you can't ask for another three days. If anything, when a woman cancels on me, that's actually a really good time to say, hey, no worries, that concert sounds amazing, totally understand. What day/days do you want to grab for the date? You actually want to reschedule right away. Got it. OK, that's good. You kind of erode that if I may be so bold. Not because you're a man. I just mean, hey, she agreed to make plans with you. The irons get cooler every day that passes. So it's in your interest to be like, hey, no worries. I give every woman one free-flake card. Here you go. All good. I'm not going to get but hurt about it. But I am going to reschedule with her pretty fast if my schedule allows. Just because I know the irons are going to get cooler every single day that passes. Got it. OK, cool. Good question. Yeah. So there's something else I wanted to ask you about. I know that would be just kind of brought up out of the blue. But so I've been doing just a lot of stuff in my new city, right? Like just trying to make new friends get a new activities. I go to improv classes now, which is really fun. Nice. Yeah. I know you've done that before too. I've been doing yoga as well. And I was wondering if you could tell me a bit about the nuances of social circle dating? The first question with that is like, so I'm part of a bunch of different communities now. And I've told you about some of them. And I keep running into this thing with women where I have taken some risks in like being more direct with some of the girls that I meet that I'm interested in where I'll just ask them point blank like after the interview. At the event or whatever that we're at, just like, hey, you want to go on a date if it feels like we're vibing. And a lot of times so far, no one has told me that I'm a creep yet, which is great. But I won't lie, I definitely worry about it. Would it support intimate social thing? Because you know, I don't want to rock the boat. But you know, I get this answer where they're like, oh my god, you're so sweet. But like, I'm not dating right now. Do you just want to get coffee instead? And I'm not sure what to make of this. Like if this is really just, I'm not interested or like, I'm not interested right now, but I still want to hang out and keep in touch. Because like, if I was a girl and I wasn't interested, I would just say like, I'm down to hang out here. I'm down to hang out in a group. I wouldn't offer to get coffee. That sounds like a date. Right. Some different women move at a different rate of speed depending on the woman. And she might, some women say, you know what, I'm definitely socially attracted to him. And so being socially attracted to a guy is actually a beautiful place because that's the path to being romantically attracted to you. She might just not know you well enough to find out if she wants to date you. So hey, let's meet for coffee. It's not the friend zone per se, but it is, let's be friends or friendly first and then explore things, even if it's just socially. Okay. So I guess my answer for you would be, it depends on how intrigued and interested you are in getting to know her. If she's just dynamite and really intelligent and warm and beautiful, then I would definitely have the coffee hang worst case scenario. You end up with a really attractive female friend, which can be very valuable in social circle dating and just helps you be a more elevated guy with women and men in your life. And if it also creates some chemistry, a lot of women, the beautiful thing about what attracts women to men is you and I are attractions like a dimmer switch. Hot girl switch on. Not hot or not our type switch off. Women are more like a dimmer switch, set up a up and down switch. And so a coffee hang with you more time in the improv class or whatever the social circle setting is. These emotions and romantic desires can get turned up just by being around you. So I would definitely consider it. Okay. Yeah. So the main fear that I have around this is I really would love to just get coffee with these women and like hang out and just feel it out. What I'm worried about is like, I've been too afraid over the last like eight years or so to ever hop into like a friendship with a woman where there's any possibility of attraction from my end. Especially because last year like I did have to cut off one of my friends were like it got too deep like the relationship was like way too intimate and I was attracted to her but she was dating another guy. And I finally was just like this isn't working for me like I just need space. I need to balance right and she did not take it well. So that's more what I'm afraid of is like I just do it know how to read these women if they're going to get angry at me like let's say I do hang out with them right and like it could just go nowhere but if I develop like feelings and they don't I wouldn't really want to hang out with them anymore. Just because it would be bad for me and that's why I'm afraid to even start is I was like what if this is a gateway drug and the harder stuff you know. So the ultimate fear here it would be that you develop romantic feelings for a woman and she just sees you as a friend and feeling like that would hurt. Yes but even more so than that like I don't want to be another statistic where like I've just seen so many women on like Reddit or whatever just hammer men and be like what the fuck is wrong with men like they they only are friends with women that they're attracted to or like you know fuck men for developing attraction out of a friendship for something like that right and it looks as like a moral judgment on me that might reverberate through the social circle that's more what I'm trying to avoid. You trying to avoid showing up on a reddit board? Yeah or like you know if I do just like make how I would like to go about things is just have female friends and just like walk around and if I feel attracted to someone to just ask them out but the reason I don't do that anymore is just because I'm afraid of like if I do that then everybody else in the group might judge me and think that I was only hanging out with her because I wanted sex or something like that right. Right these sound like some of those old stories that you and I spoke about in our very first phone call. Yeah. Yeah. They're still there. These seeds of doubt are there. What do I what catastrophe are you most trying to avoid right which is usually some variation of oh I will be destroyed on reddit or tic-tac or shunned in society. Yeah exactly like I don't want to get kicked out of the group and have a reputation where then no woman would ever like touch me with a 10 foot fold. Right and that's an understandable fear but it's not very real world. It's coming from a very psychologically healthy place for what it's worth. It means you're normal and healthy and aware of your place in the world. You want to get along. You want to be a man in society. You know who doesn't think this way. Sociopaths. Creeps. Men without empathy or kindness. So the very fact that you have these reservations is actually coming from a really great place. At the same time sometimes too much of a good thing can become of Something that creates resistance and fear bottom line is you want to Move toward what you want take Intelligent right action toward what you want and not live your life in fear Unless that fear is literally something you can actually be afraid of and in my opinion all the things that you've always been afraid of never ever ever fucking transpired The worst thing that you had happened to my knowledge is okay a woman you were dating loss interest or an approach. She said no thanks But have you ever shown up on tic-tac reddit? Have you ever ever been flamed in some Facebook groups here in knowledge? I mean not yet. It's easy for me to think that like yeah, even your answer is your cut your your speaking through those those old beliefs of fear Not yet, but Connell what if? Yeah, yeah, let's look at this rationally What would you like to do in your social circle? And I'll give you my honest answer if if you want to do something that seems Societally strange or would get you in trouble. I'll tell you I'll protect you as best I can. What do you want to do? Well for starters, I want to be a bit more aggressive or perhaps authentic with Dating in my communities a big example is like my yoga studio, right? I love this place like it really vibes with me I'm starting to make some good friends and stuff But there's also girls that show up from time to time that I think are super hot or like totally my type Yeah, no more and this has been something I've always wanted for myself But felt really powerless to get it and I would just wait for them to come to me which which never happens right and Yeah, so and then I would be like okay, but you know, it's risky So I'm just gonna keep coming back week after week. I saw that this girl comes to this class I'll just come back here and then I'd never see her again, right because a lot of these people just come for one time and then Don't ever come back and I missed my shot. Play out the thing that you're afraid of though What is the what is the thing that you're afraid will happen that's creating the fear because it this is all about fear that's pushing back against you What are you afraid of? I See this woman. I walk up to her and I say very directly like I actually tell her why I'm talking to her. It's like hey like I think you're so cute like I love your outfit whatever and then like You know, just like you want to get coffee sometime and all the other people in the yoga class like because I'm usually the only guy like they all overhear me and then they all look at me and go like Hey, that's not appropriate. Like this is a safe space like we don't do sex stuff here like you fucking pervert Okay, I gotta hear I I like it. You sound like you're on stage there like you're gonna be doing it in front of all these people I think that you have slivers of of Granes of genuine Cauchy's cautiousness fear that's reasonable but you're letting it grow into like giant stocks Here's what I mean walking up to a woman being really direct saying hey, you're really cute. I wanted to meet you I would not do that in yoga class all things equal. I would do that at the bar on Friday night I would do it at a on the street corner random place where you're probably never gonna see her on the social circle again A direct approach is Powerful, but it's also polarizing And you're gonna get a big thumbs up or a big thumbs down you know this because you've approached countless women since we first started working together, right? So you've probably seen how you get a pretty polarizing answer often is that fair to say Actually, no, I don't always get a polarizing answer. Okay. What do you typically get? Well, even in the last couple weeks it's like sometimes I go up to them and they're just like oh cool Thanks, what's up? We just start talking and then I asked them out and they're like I'm actually not single But they did they weren't threatened by me they were just down to chat great Oh, I didn't mean to say that polarizing meaning a lot of women will be threatened It's just that you're gonna get a pretty quick answer. Yes. I'm into you. No, I'm not Or yes, I'm available to date you know. I'm not that's what I mean by polarizing Oh, yeah, yeah And if you're gonna get the whole I have a boyfriend thing It's usually gonna come off of a direct approach where a woman just isn't in the mood to be quote unquote hit on or flirted with That's what that's the point I was trying to make and So back to my suggestion the way we approach a woman will change based on the social context I would gravitate toward direct approaches in places like like you just described at a park or a bar or You can go direct or indirect out at let's call it in the wild versus social circle in the wild approaches your choice be direct be indirect Tell her she's cute Tell her that you want to know that if she's looking at bugs in the dirt either it can work In your yoga studio I'll actually agree with you that the right way to approach that woman as you describe that situation would be more indirect than social playful or sorry not playful a friendly friendly where you would Approach her quote unquote you would go up to her after class or maybe before class And just have a normal authentic social conversation for a minute or two Get to know her mix some small talk and you're you're looking to your readings your reading signals and also trying to create some signals And then that's how you can then Know that you can take the next step without doing anything that the room is gonna turn and say you know like game of thrones shame You know you just walk up and say hey, that's a really cool yoga mat. Well, what color is that and you're just shooting the shit Which do you think you're gonna get the The shame from the rest of the room if you do that Not at all and that's how I've been going about it okay I also usually in that scenario like The woman doesn't Really engage with me that much which is maybe that's just the signal that I'm looking for which is I'm not interested I was more wondering if it was me not being direct enough or just like Them just not being interested and I'm doing it right Well, we'd have to dive deeper into the conversations you're having with women in a social circle setting like this but essentially you want to you want to create social rapport Get her name give her yours Still you still want to do what I call What I call mandal woman communication But not necessarily in a direct way. It's more about being expressive still playful fun Not necessarily flirty although you can start to do that and then how does she respond to those signals right? Uh And if if if you get a sense that she's just not feeling it other than as a friendly chit chat at after class Then you don't ask her out And you don't have to risk the group's finger wagging But you've you've gone on enough dates and approached enough women by now to be able to read when a woman is socially interested and maybe starting to get romantically interested right I suppose yeah like if she's you know talking back to me or like sort of body language is shifting more towards other than a way um Yeah, this is in like what would you do to like try to get her number or whatever just like Hey, you want to hang out some time or like Well before you think how do I get her number? I always like to think okay. How can I make her feel good How can I have a good conversation with her you're but you're gonna get what you first give So I'm thinking all right. I want to have a good two-minute conversation with this woman and Try to make her day better maybe show interest in yoga, but maybe talk about things outside of yoga That might help make a stronger impact Not that you I'm not saying don't talk about yoga, but I've never done yoga Class Types of approaches. I've never been a big group Jim group class guy But the closest parallel I have would be the improv community I'm a part of and used to be a bigger part of when I was single and socializing Where I would just talk with women and other people in the class before and after and then And I would play a longer game here. We're talking an eight or ten or twelve-week course And I would just focus on being good company being present Talking to women one-on-one, but I'm not thinking okay. I must ask her out. It would be a it would be a longer play Be a slower it is a social circle dating and approaching Or social circle attraction is a longer play Typically it's a longer play. It's not like oh, I'll talk to her for two minutes after class and then get her number that's possible but Some sort a lot of planets have to align for that to happen Just so I understand the context the the yoga Setting you're describing is it a group class where the same people are there all the time or is it different people filtering in and out? That's the thing if it was a group or it was the same people there all the time I would it I initially wanted to do it you were describing That's what I was expecting I would say that some of the people are there all the time like obviously is the same instructor community And that's like the core of group but it's actually kind of different people every time other than me. Okay. Yeah. Alright. So that was what threw me off is I was like, well, I just missed my shot because like this person is never going to come back. I'm never going to see them again. I mean, not a good deal, but it did get me curious of like, well, then nothing bad would have happened if I had just gone up and shot my shot, right? Even if it was for low. That's good to know. That's really good context. You don't have to worry as much about, I'm not going to have to see this woman every week probably if it gets awkward or doesn't go the way you want. That's a nice free thing to not have to worry about. So okay, well, you could do this then. Here's what I used to do when I went to drop in improv classes. Do you know what a drop in class is? Yeah, that's what I go to as well. Oh, there you go. Basically, it's a drop in is, you know, you might see some recurring people, but it's different people every week, at least in my experience. And I remember there was one improv Saturday, years and years ago where there was just a really attractive, charming, interesting woman who was totally my type, I thought, and I was single at the time. And I just remember thinking, okay, all I want to do, you want to small chunk this, AJ. I just said, okay, let me see if we can start a conversation in last two minutes. Because one of the core things that you and I worked on, and maybe you remember this, as I said to you once, when you approach a woman, your first goal is you just want to, after getting over the approach anxiety, you just want to get to the two minute mark. It takes two minutes of one-on-one conversations with a woman who you just met. Two minutes minimum for you to have a reasonable, possible chance of a phone number in a date. Any less than that, and then she just doesn't have enough experience with you. So at this improv class, it let out on a Saturday afternoon, I walked up to her and I said, hey, that was a really awesome scene you did playing the doctor. And, you know, she's a cute brunette and we chatted. And I remember we walked out together and I made it so that we were walking out together I tried to. We just were walking in the same direction. And we walked for about three to five minutes. We were both head in the same direction. And then finally, it came to that point where it was time to part ways. But by then, I'd gotten three or four minutes of conversation with her. And that was enough for me to say, hey, by the way, would you like to do number some time? It'd be nice to talk to you some time and maybe get coffee. I'd like to know you better. And I wish I had a success story to share. She had a boyfriend. She wasn't interested or she wasn't available, but she was flattered. Yeah. And I was within my rights to ask because she was talking to me. I had signals. She was walking with me. But the first things first, I would say, you just want to try to get to the two minute mark if possible. And if you do, maybe there's another minute, you can steal. Maybe there's another minute. And if not, then I would hold off on waiting until the next time you see her. Because if you can't get those two minutes of one-on-one conversation, there's really no point in even going for a number. That makes sense, yeah. And by the way, I would call that a success. Like, you had a good conversation. Like, nobody kicked you out of the community. Right. And it was just that she wasn't available. I mean, that's just the name of the game. But it's like, you did everything right. I would be happy with that, you know? Oh, no. I was really chuffed, but I did it. For many times, I didn't do it and wanted to. I went out, but this day I said, OK, I really want to just see if I can make something happen. And I had other dating successes and dated women and improv classes. And plenty of times, I didn't hit on anybody. I just just taken the improv class. But I think a bigger thing that might help you here in our time left is, I feel like you have an understandable but a limiting belief about it's wrong or weird to seek romance in a social circle. Yeah. Yeah. Like, unless it quote unquote happens naturally without you doing anything, like if the woman sort of comes to you. That's natural. I mean, I've seen it happen sometimes. The natural is that the natural state of men and women, the woman comes to you? I don't know, probably not. No sapiens are what? A couple hundred thousand years old. Who do you think is done more approaching? Men toward women or women toward men in nature? OK, I don't regret what this probably meant towards women. Yeah. Men take action, women receive. Men lead, women follow. Within reason. Lead the dance. I mean, now there's exceptions to this. But generally speaking, man act, women react. Men lead the dance, women follow. So that's you're actually quite, you're doing your natural job as a man to take that chance. You are. Yeah. Yeah. So I think your limiting belief is like, oh, well, it's not natural for me to do it. It's actually the most natural thing in the world. It's only 200,000 years old. It's only how our species has procreated for a couple of years. He's gotten this far, yeah. Right? [laughter] I'm not saying it's unnatural for a woman to give you signals or to come up to you. I'm just saying it's not the usual. It's not the standard. So your job as the man is to go talk to that woman who you are interested in or at least interested in talking to. Now, the question is how we do it in social circle. So we want to be more indirect. We want to be more light and playful and not like sexual. Keep it g-rated. Keep it light. Keep it playful. But, yeah, I feel like you got this belief that says, oh, it's wrong for me to do it. I think it's right for you to do it. I mean, it's what we do as men. And I feel like the other belief that might be holding you back is that it's somehow weird or wrong for a man to make a move, make a risk. Here's the kind of behavior that could get a guy in trouble with a social circle. He approaches a woman. She says, oh, you know, she shows he's not interested. She's not interested. And he stalks her and follows her home. That's not you, obviously. Not anywhere near you. Right. The men don't get in trouble for taking a romantic risk. The only time men get in trouble is they take a romantic risk. The woman says, no, and he says, you fucking bitch. Or he doesn't take no for an answer. That's harassment. That's literally harassment. Feel free to read chapter 13 of my book is the Me Too chapter, the How to Date and the Me Too Aura chapter. You might want to reread that where I talk about some of these things. Like, hey, Connell, is it weird and creepy to take a shot at love? No. That's what our job is. Joe from you. He's going to get in trouble on TikTok and Reddit. You're just to do chatting up a cute girl in a yoga class. And if she seems interested, at least socially, keep chatting for another minute. If she doesn't, you can read that as maybe she's not interested or just this isn't the place where she flirts. And then you can pull back and you don't have to be afraid of getting in trouble. Right. And then in that second case, I can like stalk her and find out where she does flirt and follow her home from there. She wants me to. She's playing hard to get. Look I've approached more women than 99.0 something percent of men and I'm happy to say I've never had any knock on load. Never had any kind of weird issue with getaway creep. You're doing this is terrible. Certainly never had any kind of harassment issue. Can't say it would never happen. I highly doubt it because I have a girlfriend. I only approach with my clients. No, the guys you get in trouble in these areas and they're very few and far between, but it's guys who are just not you and not this listener of this podcast. The very fact that you're worried about this shows that you're not that guy. That makes sense. The worry is understandable. I'm sorry. Go ahead. I had one last thing I wanted to ask you about if that's okay. Go ahead. I think you might appreciate this one. This is on the vein of what do I say. What I'm flirting with a woman. I tried going out to the bars recently with one of my friends who's gay. She's a lesbian. Good friend of mine. We were going to go to wingman each other. I've never done this before. I've never had or been a wingman. But as it turns out, I'm a great wingman before gay women because I have the gay dar. Because of who I am, right? A driver's super forester. I'm into improv and rock climbing. I get like outdoor adventure. You might be a gay woman, AJ. I am. Yes. I am a lesbian. I'm really gay for gay women. So whenever I would inevitably be gay women, I would pass them off to my friend. "Hey, have you met my friend?" That was great. But then I inevitably ended up stagged because I was so good at setting up my friend. I ran into this issue that I've run into a lot before, which is why I just hate bars. I hate parties. I've just had no success in these venues. Because I get cock-blocked, even if I did have the courage to approach the gorgeous woman and we were talking, her friends would inevitably come up with a reason to pull her away and shoot me a dirty look. They could tell what I wanted. they immediately would just like without being direct about it, like just, you know, "Oh hey look at this on my foot here, why don't you sit here and then just like leave me awkwardly standing there next to this group of friends." Um, and to be clear, like I did introduce myself to the whole group as well, like in this one instance, like the woman was standing kind of off to the side, that I was talking to and so like it, it floated organically, it wasn't like I just barged into a closed circle and pulled someone out of it, right? Um, but that was really confusing. I just don't know if you read into that or like how you ate do stuff in bars and be like when people are out in groups, um, and if you're single or you have one other friend, like how you keep from just being rejected not by her but by like her friends. Do you know what caused the social rejection, like what they were feeling about you? Did you get a sense of that? No, I don't. I have no idea. I just concluded that it was because I was a creep or something, you know, but I don't know. Dude, could you, you're the, you're among the least creepy humans I know after me and my two cats, but they're not human, but I think of them as humans. There's nothing creepy about you. Zero. If anything's creating a sense of creepiness, it's, it's self-consciousness, which reads as insecure, which reads as tentative and that comes across as a little bit soft and tentative to women and that can actually make them feel uncomfortable and then they mistake you for a creep or not a creep, but quote weirdo. So, repeat after me. I, AJ, I, AJ have zero point zero creepiness in my body. Zero point zero creepiness in my body. Because if I can walk up to a woman in a park. Because if I can walk up to a woman in a park and talk about dirt and bugs and talk about dirt and bugs and get a date or at least get a number, ain't nothing creepy happening. You get it, right? Yeah. Yeah. I think, look, I wasn't there. I can't read their minds. Who knows? Maybe they're being defensive. They're like protecting their group. Maybe, maybe the last guy who came up to them was a creepy weirdo and they were taking it out on you. You really want to walk through the world as best you can, especially in a loud, large, allowed intense environment like a bar or club and just say, look, I make no apologies for my desires as a man and my socializing and there's nothing creepy about you. You're the opposite of creepy. Let's stop using that word. What's the opposite of creepy? What agitators, the opposite of that? Lovable, accepted, acceptable. I like that. AJ, the lovable. There's your new higher self name to test drive. Go out this weekend, walk up to a group of women say, hi, I am lovable. That's really, I love that. That's really great. Seriously, I'm going to do that tonight with my client Chris. We're going out tonight. I'm going to give him the lovable opener. Love you. Do you know how that goes for you? That sounds awesome. Only have kidding. The words we use make a huge difference in how we walk, talk, feel, words matter, right? I know you don't literally say the C word when you're out in the club, I assume, but I know you're thinking it. Creepy, creepy, creepy, am I being creepy? Am I creeping out? No. It's not just that. I just don't know what to say to these people because, well, one, I don't drink. So I'm not drunk, right? I'm stone cold sober in these places. I just don't know how people play. What do you talk about? That's just, I just don't know. It's a lot different than just being in a park where you can just be yourself and talk about your interests. Let's end on that then. Let's talk about what to talk about. That's a great question. Yeah. Give me a context. Give me a hypothetical, something that's happened or something that might happen where you're not sure what to talk about or what to say. Paint a scene for me and I'll guide you. Great. Well, let's go back to the scene then because I've been thinking about it a lot. Like, okay, you're on a rooftop bar, right? It's packed like elbow room only kind of a thing, right? Everyone's standing. And you're there by yourself, but almost everybody else there is in groups because my observation here has just been women don't really go out single. Right? Yeah, they, and for obvious reasons, right? I'm sure it feels safer to just be in a group or like, anyway, I saw this like gorgeous woman in this striking red dress and she's standing at the head of a table where her friends are seated at the table, but she's kind of standing because there's not enough room for everybody. And she's not talking to anybody. So I walk up to her and I just introduce myself and go, Hey, look, I just saw you from over there. Like I just loved your dress. Like you look gorgeous tonight. And it's like, love, I gotta thank you. And you know, start just talking and that's where I think the conversation got really boring because I was just asking her about, Oh, what are you up to? Like, you know, what do you do? And she's like in a med student or something, which was really cool. I was like, Oh my god, you must be a genius. She laughed, but yeah, I just didn't know what to talk about. I was like, I have no idea how to be flirty in this context. And it was such a weird dynamic where it's like, you have this big group of friends. I have nobody. Like if I try to pull you away anywhere, talk to you one on one, like, they're going to be like, who the fuck is this guy? Did the, did the fact that you were there by yourself? Was that getting you in your head? Absolutely. Okay. The first thing is I want to say, I'm friends with everybody here. You're just a guy in a bar. So again, I, I drone on and on about mindset. And that's 80% of success with women. But it's true. It's like if you walk around feeling like you're the odd man out, that's going to come out in your voice, your body language, something. Because you're going to be, you feel what you focus on, right? We feel what we focus on in life. So if you feel you're the weird guy because you're alone, then I'm not saying you're going to be weird, but it's going to make you more insecure and less confident, right? So yeah, the real issue isn't what to say, although that's important. Those are the mechanics. The issue is your mindset is like, oh, I don't belong here or they might think I'm strange because I'm by myself. Here's what I want you to do next night. You go out, walk up, face your fear. Hey, just saw you ladies. I'm here by myself, but I'm lovable. That's such a great line of. Oh, no, women don't give a fuck if you came with an entourage or if you came by yourself. They're just, all they care about is, oh, here's a guy who's here to socialize. I wonder if he brings value to my life. Just judge you on how many people you're with. Do you actually believe that it's not like they're like, who the hell is this guy? Why doesn't he have friends? You know how many times I went out solo? No, I don't. I can't, I can count on one hand. I went out dozens of times solo. I can count on two fingers. The amount of times women even asked me who I was there with and zero times I was judged for being solo. Zero. They might have said, hey, who are you here with? And I might have said, oh, I'm out solo. I might have said, oh, I'm meeting friends later. I might have had a little cover story. Feel free to use a little cover story. Hey, who are you here with, AJ? Oh, I'm meeting some friends in a little bit. Just, just me for now. If that makes you feel more confident, go with that. But if you really want to blast this fear out of your system and so much of getting what you want with women and dating and how you feel is about literally, not literally figuratively facing that fear, walk up and say, hey, group of nine women, I'm here solo. I'm AJ. And face the thing you're afraid of. Anything, they'd probably be impressed that you're solo and talking to them. But chances are they just were like, oh, hi, hi, AJ, by yourself. What's up? They probably won't care. Tonight I'm going out with my client, Chris. He's scared to death of being the weird old guy. Because he's over 40. So guess what he's doing. You know what you're, he's walking up the 22 year olds. His opener is high. I'm in my 40s. I have to find a New York City job to torture him. But with love, there's just so many things that come up and scare us, right? And the only way to beat them is to face them. Tony Robbins has a good line about this. He was like, you know what? Everything we're afraid of. It's all fucking bullshit in your head. But it feels real. So what you do is you grab your chair and whip because there's a lion. You think there's a lion there. So you grab your chair, you grab your whip, you face it with courage, and then you find out, oh, wait, there's no lions. Just kitty cats. Now with dating for you, the lion is, oh, I'm going to be creepy and weird. Or I'm the weird guy by himself. And they're going to look at me less in a lesser way. Right, right. And unless you can prove, you got to give your brain evidence that that's bullshit. I can't talk you into feeling that way. I mean, I can give you the pump, the pep talk, but your brain needs proof, not my promises. So if you really want to blast this out of your system, this weekend, go out solo and maybe maybe make a couple of social approaches. Just be friendly with a couple people. Make some bar friends. Now you have a couple of safe bases, which might give you some little bit of that social momentum that you like. So you are with a couple people. I'm not saying you have to pretend like you're with people, but it might help you to just chat a couple people in a friendly way. And then walk up to women and say hi to whoever you want. And if the topic of who you're here with comes up to say, it's just me tonight. I'm solo, but I'm lovable. That's the mindset that you're part of. I think I might try that tonight. Do it. It's so fun. It's horrifying at first, but it's so powerful. Do the thing that scares you. Here was the my big other than just approaching women, which was the scary thing for me for 38 years. Then the next thing was, I'm so afraid to say the word sexy. I'm so afraid that's so weird to walk up to women and call her sexy. And one of the biggest nights of my life was my coach Anthony, a guy named Anthony Rezonello. Great guy. He's on Instagram. He's a kick ass coach. One of my better coaches. We went out one night and Anthony said, all right. Well, I think I said it actually, but he supported me. We said, Colonel, the only way you can approach women tonight is you must start with your sexy. (laughing) I was petrified. First three or four were very wobbly. Very like, this is at a rooftop bar, plunge lounge in Me Packing District of New York City. I don't think it's there anymore. I mean, it's not called that. Anyway, first three or four approaches of this rooftop bar, I was like, hi, you're sexy. (laughing) And they're like, okay, great, bye. It wasn't mean, but it was like, no, thanks. Four or five, you're sexy icebreakers into the night. I started feeling a little better. Started kind of owning it. Owning it. And I remember half dozen in. And also, I wasn't really feeling it. I was doing it as an exercise at first, which is okay. But then I started to feel it. Here's what authenticity really starts to show benefits. So I was like, whoa, Anthony, look at that hottie over there, fuck. He's like, yeah, she's hot. Go talk to her. I walk over, hey, what's up? You are so sexy. And she looked at me like, hey, you're pretty cute too. Mm, instant. Wow. Yeah, not by the way, I don't remember if we didn't date or anything, I don't even know if I probably got a number. I don't think I ever met her after that night. I mean, but it was like that instant like, hey, you can go up to women at a bar at night and say you're sexy and a lot of them like it. And some of them weren't into it. But the more I owned it and the more I started to believe it, that's when it actually started to work as a self-fulfilling prophecy. So for your version of that might be, hey, you guys, I'm out solo tonight just meeting people. Don't make it weird. Don't say, is it weird that I'm out? Don't do that. But yeah, go out tonight, say, hey, what's up? I'm out meeting people. I'm here solo. Just making friends. How are you? What's up, I'm AJ. Or whatever you might say. So basically face the fear. That's what Chris will do tonight. Hopefully if he does what I ask him to. Now what to talk about though. Pretty simple. I think. Do you remember how long the conversation was with the woman in the red? It wasn't that long. We were talking for maybe like two or three, maybe five minutes before her, you know, friend stepped in. But yeah. Okay. It sounds like you got stuck into asking a lot of questions. Probably. Yeah. That's normal. Questions aren't something to be afraid of. I like to think. Here's a look. Here's a, this is. This might sound like mediocre game, verbal game, but it's actually not a bad thing to say. Is you, you walk up to that woman. Hey, red dress. You have great style. You said something like that, right? Your beautiful, great style. Nothing like that. Yeah. So you can keep talking about that. It's the topic so that the way you break the ice for the woman, think of that opening ice breaker as a conversation thread. And you can keep pulling that thread. In this case, it would be the thread of her or the topic of style, her style, your style, men style, women style. You can talk about that for a minute or two. Okay. Keep talking about the thing that you use to break the ice. That's the simplest way to do it. Hey, excuse me. I just saw you. You have an amazing red dress. She loved it, apparently. And then you might ask her about her style philosophy. Or you might say, can I ask you, what do you think of my style? My dating coach tells me it needs improvement. [laughter] Hey, you haven't seen me recently. I dressed well now. Before. Before. But that first thread, what you talk about the topic doesn't matter that much, as long as it kind of makes sense in that world. So I like to keep it simple. Break the ice with whatever compliment, a question, or an observation. In this case, it was an observation that you turn into a compliment. Right? Pull the thread. Oh, clothes style. Your clothes, my clothes, fine. That'll last a minute or two. Then get her name. Did you introduce yourself and get her name? Yeah, yeah, yeah. Great. Awesome. Now you're not two strangers. You're two people getting to know each other. AJ and Reddress QD. And then all you got to do then is switch to a second topic. And that second topic can literally be like look around you. I like to literally look around the environment. What is the next thing we should talk about? Why they're all out together, or you know how she knows them. Or maybe there's something. But it's literally how the conversation went. That's fine. Exactly like that. Yeah. Okay. Yeah, that's fine. Keeping it late. Now the only thing I noticed as you were retelling your interaction with her was was you asked a lot of questions. If you find yourself asking like three straight questions, interrupt that pattern and share something about you. What did she know about you? What did she learn about you? Gotcha. Oh, well, I think I did. Like yeah, you know, I just moved here like three weeks ago from California. And I don't remember the whole conversation because it was like a couple weeks ago at this point. Okay. I will say I think part of the problem was, yeah, when I walked up to her, I don't think I was feeling very confident. And then she gave me a sort of like, she was still talking to me and making eye contact and stuff, but it wasn't like, it was sort of lukewarm. And that was when I was like, she wants me to leave like fuck, like I need to get out of here. How many other women had you approached before her? Gosh, actually a lot. I hadn't rejected a lot up to that point. And so I think that was also playing into it. Okay. Just wondering because if that was like your first one of the night, then that's different. But you had some social momentum. You were taking action, I should say. Yeah, I would say so. I would say, think of an approach like, I want to make an impact, a positive impact. How do I make a positive impact? If you primarily ask questions, it's hard to be impactful. You're making her do the work. I like to think about what am I thinking and feeling? Or what's a really honest, real raw opinion? You're a very honest opinion, a guy. Share that. How do you feel about, okay, you know, we know how you feel about her red dress. How do you feel about the drink she has, the way she looked at you? How do you feel about the environment? You love the bar? You hate the bar. You love the music? I like to use love and hate a lot. The words literally. Oh, I love this place. This music is awesome, but I fucking hate that DJ over there. He never plays the good shit or whatever. So you can use language. It makes a stronger impact. But all of the what to say in topic based things and flirting and what to say is so important. It's what I teach more than anything. It works best when it's built on that foundation of, I am lovable. I am, I have so much value to offer the world and offer people. And I would like this woman to like me, but I don't need her to. Nice, okay. So we want to come at that place from like, ooh, I'm here to make an impact in a positive way. I hope. It's sort of like we want to get her reacting. I'll leave you with the RLL and shortly here with this. This is kind of a big picture of things. It's kind of an advanced thing for guys like you who have done a ton of approaching. I want to test drive this as well. In every approach between a man and a woman, when a man approaches, there's one person who is doing more, who is in action mode, and there's one person who is in receiving mode. Or put another way. There's one way. One person who is being more reactive and the other person who is being more active, if that makes sense. Both in words you say, but also emotionally reactive. Emotionally centered and solid and giving would be, "Oh, I'm making an impact. I'm going to say this funny thing. She's going to love it. I just feel in the zone. I love sharing." Emotionally reactive is, "Oh, does she like me? Am I a creep? Is this working?" In your interaction with the red woman, dress woman, who is reacting more to whom? I think I was reacting more to her because I was coming at it from really looking at the way she was reacting to me and wanting to fix that. I think I'm doing something wrong because she's like, "Yeah." No more of that or at least no more doing it without thinking about it. I want you to be the white billiard ball. And women at a bar or a park or out in the world, they're the striped and colored billiard balls and you are impacting them. If you're standing there and you're letting yourself fall down this little mental rabbit hole of, "Oh, does she like me? Am I enough? Am I a creep? What do I say? You're reacting to her." And that takes away your masculine core essence. And that's not something women are looking to fuck. They're looking to date, fuck, connect with their feminine. They want to receive, right? You want to be that billiard ball that smacks into them figuratively. Literally later, if it goes really well. But you want that to be that action. That's the state of nature. Mask you and feminine, action, reaction. If I can be candid here, penis enters. Vagina receives, literally, right? Men ask women to dance, women say yes or no. So we want to be that active force. A positive force, a beautiful force, a heartfelt one, kind, all the wonderful things that you are. But yeah, boom, I'm a man. You're a woman. You're going to react to me or try to, or I'm going to try to get you reacting to me. Because that's what she wants as well. If she senses you are in your head saying you're doing the thing that you think needs to be set or done or quote insecure, women don't use this language I'm using. But they're like, oh, he's not. He's not what I want. And that's nothing to do with your value. It's just like, oh, again, women don't say he's being reactive. But bottom line is she's not feeling the way that she wants to feel when her feminine side is lit up and impacted by a funny man who's on his path and who can't be moved emotionally. Can't be hurt. Yeah. I like that. Thank you for sharing. Yeah. I was just doing this last week at a client in town who was visiting from Taiwan, Erin. And he was quote unquote reacting to women into an extent. And I say, cool, your next three approaches, I want you to get them reacting to you. Now part of this is social. I'm also saying I want you to make statements, share, give, get her responding to your energy. So part of it is a social dynamic, but it's also an emotional being on the action side, not the receiving side. So we did a few approaches and I said, I don't care what you say. Oh, I just want her to react to your essence. You get her responding to you and stand there like, you know, like a solid rock and let her respond to you. He did a few approaches and you could just see the feminine just go, who is it? This guy just came up to me and his approach started going a lot better. Nice. Yeah. Awesome. Well, I actually need to get going, but there you are marching orders. Then I'll leave you with this. Go whatever you do tonight or this weekend with approaching. Just remember, you are the masculine. You were acting upon her in a positive way, but a dominant way. You actually responds, whether it's energetically, emotionally or both. That night with Anthony, I was walking up to him and saying, hey, you're sexy. They were responding to my masculine essence and it started to go pretty well. So feel free to test drive that if you want. Sweet. We'll do. All right, man. Thank you. By the way, thank you for listening to this podcast, dear listener. If you would like me to help you go approach women and make you walk up to women and say weird things like, I'm lovable. Go to datingtransformation.com. You can book a free call with me that way. Thank you so much for listening. [MUSIC]

Podcast Summary

Key Points:

  1. AJ, a former client, returns to discuss advanced dating challenges after successfully overcoming approach anxiety.
  2. He shares a success story of meeting a woman in a park by using a simple, authentic opener about a caterpillar.
  3. AJ struggles with a canceled date and seeks advice on how to follow up without losing her interest.
  4. The host advises against confirmatory texts that invite cancellation, recommending instead assumptive and playful messages.
  5. AJ worries about social circle dating, fearing rejection, being judged, or developing unrequited feelings that could harm his reputation.
  6. The host reassures AJ that his fears are common but often unfounded, encouraging him to take intelligent risks and pursue what he wants.

Summary:

In this podcast episode, dating coach Conno Barrett hosts AJ, a former client who has made significant progress in approaching women and securing dates. AJ recounts meeting a woman in a park by asking a simple question about a caterpillar, which led to a date plan that later fell through due to a scheduling conflict. He seeks advice on how to handle the situation without seeming pushy or losing her interest.

Conno suggests using assumptive language when confirming dates, such as playful references to the planned activity, to avoid giving women an easy out. He also recommends rescheduling promptly after a cancellation to maintain momentum. AJ then raises concerns about dating within his social circles, like yoga and improv classes, where he fears being perceived as a creep or facing social backlash if he develops feelings for a friend.

Conno validates these fears as signs of empathy but encourages AJ to move toward his desires with intelligent action, noting that worst-case scenarios rarely materialize. He advises that coffee meetups can be a low-pressure way to build chemistry and that having attractive female friends can be valuable. Ultimately, Conno urges AJ to stop letting hypothetical judgments from strangers dictate his behavior and instead focus on authentic connections.

FAQs

Use an assumptive, playful text that assumes the date is on, like 'Can't wait for our hike tonight—bring some caterpillars!' This avoids opening the door for her to flake.

Give her one free 'flake card,' say no worries, and immediately reschedule by asking what day works for her. This keeps the momentum before interest fades.

Typically seven to 10 days, so ask a woman out sooner rather than later to keep the iron hot.

No, it's normal to ask someone out. It's only creepy if you don't take no for an answer or follow them home.

It may mean she wants to get to know you socially first. If you're interested, take the coffee hang—it can build romantic attraction over time like a dimmer switch.

This is a common fear, but taking intelligent risks is better than living in fear. Most catastrophes you imagine never happen, and you can politely step back if needed.

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