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How to Flirt So Good She Can’t Stop Thinking About You (Live Coaching with Evan)

52m 19s

How to Flirt So Good She Can’t Stop Thinking About You (Live Coaching with Evan)

In this podcast episode, dating coach Connell Barrett and his client Evan discuss how to flirt effectively so a woman can’t stop thinking about you. They emphasize that women rarely remember witty opening lines; instead, they recall eye contact, good posture, and a confident vibe that signals belonging. Evan shares a recent experience where he struggled with approach anxiety at a birthday party, but used a friend’s challenge to break the ice and build momentum. Connell reinforces that the bar for a good opener is low—simple, authentic statements like “You’re really cute” work powerfully. He recounts a Barnes & Noble encounter where saying just that led to a date. Both highlight that the conversation itself, not the first line, is what matters; women remember how you made them feel. Evan notes the importance of playing to win—showing romantic intent by giving compliments and pushing for numbers or dates, rather than playing it safe. They conclude that authenticity and courage outweigh cleverness, and that taking imperfect action beats overthinking.

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Whitty, amazing, funny lines are great, but most of the time women won't remember it. They'll remember the eye contact, the good posture, and just an overall vibe that says, "Hey, I belong here, talking to you. I wouldn't like to come talk to." Welcome back to the How to Get a Girlfriend podcast. I'm your host, dating coach, Connell Barrett, helping you know what to say, and flirt like you mean it. And let's talk about how to flirt so good she can't stop thinking about you. And to help us do that for this episode, I'm bringing back a returning guest, my client, Evan, has been on before. And Evan first came to me a while back when he was struggling a little bit with how to approach women, what to say, struggling a little bit with the online dating openers, and he's since taken his dating results to a pretty kick-ass place. Let's talk with Evan about how to flirt so good she can't stop thinking about you. Welcome back, Evan. Good to be back, Connell. Appreciate the re-envi-ing. You're here so often, you're almost my co-host at this point. A lot of guys come to me and they say, "Connell, how do I get out of my head?" I'm in my head a lot. And I used to be in my head specifically when I wanted to approach a woman, I always stopped and I said to myself, "What do I say? I don't know what to say to women." That 20 years ago, that's what got me hiring a coach and trying to figure out this whole approaching thing and flirting thing. What about you? When you think back to when you were struggling a lot more with your dating life before you and I worked together, can you talk about a time you were in your head or the pattern or you noticed you were, quote unquote, "in your head with women" and also what changed? Yeah, make me think of a few instances and still ones that can crop up now, I think the approach is such a big one that I know a lot of guys struggle with. I mean, you've talked about that. How only a very small percentage of guys have the cajonas to actually do it. But I know even now, even though I've done it hundreds of times at this point, I don't go through little periods where I still can get in my head about her if I see someone. Then the voice is crop up about, "Oh, she's too old, too young, maybe has a boyfriend, maybe not, oh maybe I'd be. " I just think of just different reasons as to why not to do it. Then I don't, whereas I know that it's just better to do it, to just talk. Because if, okay, maybe she does have, like, who cares, but then very often those things are not true, right? It often would work out in the times where I do have those kind of blocking thoughts, they end up not being true. "Oh, it's going to go poorly or whatever, where I know now after a lot of experience it's not." But I notice there's just these periods where I can get in my head about it. Can you think back to a moment when you had to talk yourself into approaching a woman because you thought, "Oh, she doesn't look approachable, she doesn't want me to bother her." But you did it with good old-fashioned courage. Actually, it went really well. I want to say it's almost every time. It's just something to agree, you know, still. Best is when you don't think about it, where I, but like, even, I just was out for my birthday with a bunch of friends with this cool lounge and there's a lot of women there, a lot of people. And so, it's my friend. Yeah, just this last weekend. And I was kind of having some choke, you know, it was like, you know, like when you're in your head too much, you end up like leering like a creep. And, you know, because you're like, you're thinking, you're kind of like looking and thinking and thinking. And I noticed I was, you know, doing that to a degree where I was just not taking action. So I was like, "Walk." I'm like, "Okay, maybe I could approach her." And what, okay, then what do I say? And what's the perfect thing to say? And I just, you know, an hour went by and I didn't approach anybody yet. There's like women all around, you know. And I was, you know, some of my friends and I like in me doing this, I think I've talked about that before where I sometimes encourage my friends to do it as well, like when we're single guys because they've seen me do it. And they kind of like, at this point, like look at me like a leader to some degree. And they're like, oh, like, and I think they, they think that like I'm maybe better than I am. Like, they see me as just as like super confident, like don't think, don't give a fuck. But really, I still have like a little bit of anxiety, but you know, I, they've seen me take that action. You know, it does still, I still get a little bit of butterflies, not nearly what it was before. But, you know, but I noticed that was having, you know, a little bit of the block, a little bit of a mental block for whatever reason that night. And what I was talking with my friends about it. And I, I think I asked one of them, I'm like, all right, give me a challenge. Just tell, just tell me what to do with the girl. And he goes, all right, see that girl there with the curly hair? Go talk to her. You know, go work your magic or whatever. And I was like, okay. And I just went and I did it. I had a great conversation and nothing bad happened, you know, and we talked a couple times at night. And maybe, you know, and ended up in like, okay, maybe it's not going to go further. And, you know, whatever. And, you know, some of that was me as like, oh, maybe I didn't vibe as much as I would have wanted to. Whereas before, I'd be like, oh, my God, I need her to like me and do it. But like, at the same time, it's like, I tried to shift my mindset of like, no, I'm the, you know, it's okay if I'm someone who says, no, you know what I mean of like, you're just not what I'm looking for. But hey, when I talk, we had a great convo. We had fun and, you know, laughed. And, you know, we talked a couple times and met some of our other friends, you know, and it felt really good and it broke the ice. And then I spoke with, you know, multiple other women that night. And so, you know, kind of got me back and to just got the momentum going once again. So, I mean, yeah, so just a very recent example of how I can still get in my head and there's, you know, ways to push through it. Right. So, you still get in your head. You still find reasons not to do it. Yet, that's what I love about that story, Evan, is you were resilient and you came up with a way to get yourself to take action. Getting your friend to say, all right, who should I approach? And that can help us smash through the resistance. So we find a way to approach a woman and most of the time, it either doesn't go as badly as we fear or actually it can go really, really well. I think the biggest problem I hear over and over again from men is, I don't know what to say. I'm not sure it'll go well and I don't want to creep around and bother her. And one of the smartest things you can do is go out with a wingman and give each other missions to do the whole night. Way back when I first started approaching women, I had this wingman buddy named Tyler and we would give each other missions to do. And tonight we go out and I do approach everyone he pointed to and vice versa. He points to a table with a really pretty brunette, her pretty blonde friend and this big muscular guy. He's like, go, go over there and approach. It's like, oh, Jesus Christ. Roof top bar called 235th here in New York City. So I had to do what I had to do. So I go over and I sit down. I'm thinking, oh my God, the guy's going to punch me. He's a big muscular dude. He's one of their boyfriends. This is going to go terribly, but I sit down and I grab his seat and I say, hey, I just want to say hi to you. You guys seem friendly. And the brunette looked at me with these big eyes and leaned across the table and she said, oh my God, you just came up to us and just said, hi, do you know what you are? And my mind, I'm like a creep who's about to get his ass kicked by your boyfriend. And I tried to play it cool. I said, I don't know. What am I? I said, you're normal. Thank you for just coming over here. And then she pointed to another table. She said, that guy over there and she pointed to another ginger in a black shirt like my doppelganger. She said, see that guy over there? He's been staring at us all night and it's creeping us out. And I got the cute brunette's number. By the way, the big muscley guy wasn't a boyfriend, just a friend. He was pretty chill. And I got the cute brunette's number that night and I thought, damn, you know, is it hard to approach women? Yeah. Is it possibly creepy? Maybe, maybe not. But you know what's creepy? It's staring and leering and doing nothing like my ginger doppelganger. The anti-connel. The anti-connel, I hope he figured it out. Although maybe more so the old conno, right? Who probably would do the same shit I do. Yeah. So what you could do for those watching or listening is, all right, you feel that anxiety, you'll lose nerves. Give your wingman a hundred bucks and say, here's a hundred bucks. I will approach every woman you tell me tonight. And if I don't do one thing, you can keep the hundred. That'll give you leverage. It's almost like accountability. It's a really good accountability. Yeah, exactly. When you and I first started working together, one of the things was you came to me in part because you wanted to approach. It wasn't just about the fear. It was about, "Oh, what do I say? How do I break the eyes with women?" Can you share some of your insights or success stories, moments where you didn't know what to say, but you figured it out or you came up with what to say? When you want to approach a woman, how do you figure out what to say? We talked about this a bit last time and I know how you teach about something relevant. It could be about her, her style, something that stands out to you, something that stands out about the situation or just like a candidate to say whatever is on my mind. I usually wean toward the situation. For me, it's a little more comfortable and one of my strengths is coming up with fun, funny things to break the ice. I remember two, one time when we were working together, you challenged me. You said, "Don't ween on that." You said, "Go, just try one of these other, just candid, just, "Hey, I want to talk." Or something like that. It made me really nervous because for me, I think it's successful when I do these things, they work for me. I think it was also a good challenge that you gave to me to just do something that doesn't have to be the most creative thing in the world. Because I think at the time I was getting a little blocked because I was maybe hovering a little too much as I was working through some, my writing team and my head was working through some workshopping material. I remember I was at lunch with some friends and there were these two girls and one was like really super cute. It just wasn't the right, it just didn't feel like the right moment. I'm with my friend. I was like the middle of the day and I was like, "What do I do?" I just kind of let it go. Then I went back to Starbucks where I was working and there, 20 minutes later, her and her friend walked past the Starbucks and I was like, "Oh, second chance. I'm going to do what Connell said." I think I had to hype myself up a little bit and they got kind of far away. I kind of left my side, it's luckily really safe where I'm at and no one does anything. There was someone there I knew. I was left my stuff there. I think I ran to just catch up and then had to catch my breath and then just kind of like walk to the side of them as they were walking. What did I say? I think I said, "Hey, I saw you guys before." I don't know if I said that. I thought you were cute or you guys seemed cool. I wanted to say hi. It's just something like that, just this pre-programmed, nothing fancy and we just had a good conversation. The three of us, I probably walked another quarter mile or more, super far away from my workstation there. She did it all over the place. A little bit of my stuff back there. My supply line was stretched. I walked all the way to the end of the other side of the beach, kind of pretending like I was going that way anyway. It was really funny because another funny part is not super relevant to this situation. The girl, I think both of them were Peruvian and my brother's wife is Peruvian and you're kind of in a small town. She ended up of course knowing my brother's wife and I was like, "Oh, shit, I hope she doesn't tell her." That this guy just came up to us and said, "Hey, I think I thought you were cute or whatever and came and flirted or what I was like, "Oh, God, I'm going to get this reputation." I didn't care that much but thought it was just kind of funny that they knew each other and went, "Oh, I hope you don't tell her." But the one I did think was cute did end up having a boyfriend and they were like looking at getting the partner visa, something like that. But still, I think that again, even if it doesn't end up in marriage, a date sucks, it's still a win. Absolutely. I think that having that mindset's really been helpful as well, that process goal. Also, you talk about this a lot in this stage in my head is also how you push to play to win because otherwise I can maybe fall into this safety mode where I'm just going to go talk to them and I'll call it a win but I didn't push past to get the number, really try to get the date or break the ice if it's not. We didn't talk for 10 minutes and we were vibing. We talked for a few minutes, I still think they're cute. Let's give the compliment. Let's do the romantic, say a romantic line or I think that was a huge learning moment where I don't have to play it so cool that does he like me or does he think I'm attracted to actually say you're cute or that. I think it's super powerful as well but I was the ass I'm just saying, making sure I play to win so don't take it too far in one direction of playing it safe just to break the ice and feel good about myself but also make sure I'm playing to win as well and take it the next level. What stops a lot of men from approaching women is thinking there's some perfect thing to say or that it has to be the right thing. It's got to be witty, charismatic, amazing and this is actually what adds to approaching anxiety. Thinking the bar is this high for how good the thing has to be to say when actually it's much, much lower the bar. One of my breakthrough moments realizing this back when I was learning this way back when Obama was president. Because I'm a guy who loves, oh let me say something witty, cool, charismatic and that was just getting me in my head and I usually wasn't doing anything. So I'm at Barnes and Noble one day, one Saturday afternoon and I see this very, very cute thin blonde woman standing next to all these greeting cards looking at cards and I just said to myself, okay, what am I thinking and feeling? What's the authentic real truth? She's really cute and I want to meet her. I walked over and I said, "Hi, excuse me, you're really cute." Three words, "You're really cute." And she looked at me and smiled and said, "You're very handsome." We were like couple of eight year olds. You're cute, you're handsome. I like you. Do you like me? It was so simple and sweet. We chatted for about 10 minutes. Her name is Lane, by the way, and got her number. And I remember she texted me later that day. She texted me and I quote, "Hey, thanks for picking me up." She actually used the word pick up as in picking me up. It's not a bad thing to try to approach, quote, pick up a woman if she likes you and likes you vibe. And it was just so simple. I said, "You're cute." She said, "Oh, you're handsome." We had a nice vibe and then two nights later we were on a first date and it went great. I just never forgot that. So if you have a fancy, cool, funny line that comes up organically great, go with it. But if you don't, just walk up and say, "Hey, you're cute. Want to meet you?" It can be that simple. Yeah, I agree that there's power to that versus coming up with the line. And I think that's probably a big point of resistance for me in the moment is trying to lean on the comfort of the perfect line. Sometimes it comes pretty quick and I have some built-in ones because a lot of times during the day, you'll see a girl working by the beach or at a picnic table or at a coffee shop and they're beach clothes, but they're also working. And I could be like, "Oh, is this your new office?" Or just something simple like that. Sometimes it'll be like Wednesday and they're at the beach and I'm like, "Who's allowing you to have a beach day on a Wednesday? How do you do that?" I don't know, just something silly like that. Just gets that. I mean, it's probably more important and powerful is the conversation itself. It's not the first line. It just opens the door. If you have a good line, it gets things started off in a good direction. But if you're being your normal, clever, nice, cool, whatever self, that's what's most important. Not the open areas that you're going to forget about that. It's really good. Maybe they won't. Sometimes it makes for a good story later. You know, like, "Oh, we came up and said this." Yeah. Women rarely remember the thing you say when you approach. They just remember that you did it. I would call foods once. It's the first week after Christmas and I saw this very pretty attractive stylish woman and the frozen food section. and she had this winter hat, a big kind of like frilly hat pulled over. She looked like the cover of the J-Crew Winter catalog, which is what came to me. And I walk over and I said, hey, I just saw you, you look like the cover of the J-Crew Winter catalog. I thought that was pretty good. We had a good conversation, we chatted, I got her number, we had a first date a few days later. On our first date, I said, so I'm curious. What did you think of me when we met? I was fishing for a compliment. My ego wanted to be stroked. I was hoping she would say, oh, you were so witty, you were so funny. She couldn't remember what I'd said. She said, oh, you know what I liked? Is you look me in the eye? You stood up straight and you look me in the eye. Just eye contact, normal conversation, showing that clear interest. That's what can make a woman really attracted to you. And think about you as, wow, finally a guy just came up and let me know he wanted to meet me and we chatted and that's more than enough. So witty, amazing, funny lines are great, but most of the time women won't remember it. They'll remember the eye contact, the good posture and just an overall vibe that says, hey, I belong here talking to you. I wouldn't that come talk to you. Well, it's how you made them feel in the moment, right? And so some of them is like having the line, they may not remember it, but they'll remember just how it made them feel at the beginning of like, oh, wow, or just playing into the general fun of it. And so yeah, it doesn't matter just yet the end of the day. How did you make them feel in that interaction? Do they want to continue hanging with you, seeing you again? So it is important thing to remember for me that maybe I'll challenge myself a little bit to do that the third column, which is what I think, what I feel is what I say. Is that right today? Yeah, what I'm thinking of your line. It's not my line. My very first coach said it to me in 2009 when I first approached the one the first time opening chapter of my book is all about that. And he said, yeah, what you're thinking in feelings, what you're saying and doing. And he was trying to say, doesn't that to be perfect? It just, you can speak your real true thoughts. He didn't say authentic, but basically you are enough. Women like you, he said, you women like you for you. I thought, no, women like me for my lines and game and cool funky shirt. No. Yeah. So I still hold onto that and it really helps. Yeah. Yeah, that matches my experience as well. I'm going to ask you to, I give you permission to brag a little bit if you want to about something. You've had a lot of great dating wins in our time together or since we started working together, you've approached, you've had a lot of dates, you've had a lot of cool experiences. Can you think, what's a moment you've shared with a woman where you said or did something and it made her noticeably more attracted to you? Or just a moment during a date where you could feel the eyes on you that she was really into you. And it's probably happened many times. But do any specific moments jump out to you? That look of attraction, that look of damn, this woman is in to me. Yeah, I think like when an approach is successful, and I think just really the things that you described, it's like if they're talking to you, that's a good sign. If they're continuing, if your conversation goes, oh my god, we're still talking at five minutes. We've been talking for 10 minutes. We're laughing, we're vibing. Oh, they asked for my number. They asked for my Instagram. That should just happen, really. So there's definitely been some of those moments. I had a big, I call it like a big win. And I think it was definitely a memorable moment recently with an approach where I was going on a camping trip and I was meeting friends. I think I was up the coast a couple hours and I had to unfortunately come a day late. So everyone was there. They were at the beach, a big group of people, most of whom I knew. So I get there late. I'm like in the afternoon, I'm walking up to the beach and the beaches, you got to walk down some stairs to get their surreled down there. And then up there, you have the changing rooms, restaurant, whatever. And so I was getting ready to go down, get my stuff. And I was just checking out the way of the land up there and what they had. And there was this girl bikini with a little summer dress. And I saw her walk by and she just went at one of the picnic benches and started reading. And I was like, now my mind naturally goes to like after all this time, just like, do I approach? Like this is what I want to do. Do I do it? Do I do it? Or whatever. So then I go into that mode of all right. I'm not going to do this. And so I was like, OK, she is really cute. And we locked eyes for a second. She looked up at me. I looked at her. And then I kind of chickened out. And I'm like, all right, well, maybe I'll get a second chance. I'm just going to go down and talk to my friends. And so I did. I went down. I hung out with them for like 30 minutes, caught up with everybody. And then I went back up because I was going to go for like a jog or something like that. And so as I'm getting my shoes on and ready, she's still there. 30 minutes later, she's sitting same bench. We look at each other again. I'm like, I fuck it. Here we go. Then a couple of lides walked up to her. And I was just like, well, you haven't moved much. I was like, just like that. And she was like, I didn't think she understood what I was talking about. But we just started a conversation. When five minutes, 10 minutes, more. So we had a really good convo. And it was kind of funny because I didn't know who she was. And I was like, yeah, like my poor word. Because we're two hours out of Sydney. And I was like, oh, well, are you from here? Do you live here or something? She's like, no, I live in Sydney. I'm like, oh, yeah, that's where I'm staying as well. And she's like, what part? She tells me, ask me what part. I'm like, I'm in Manly Beach. And she's like, oh, all my friends, all the people I'm here with are from Manly Beach. And we're kind of like remote. There's not like that many people there. And I put it to him, like, wait, are you with this group here? Like this volleyball group? She's like, yeah. I'm like, really? I'm like, who are you? Because like I usually know everybody, you know? And she's like, oh, I was just invited by a friend who's down there. And I decided to tag on. So she was actually with the group that I was with. So I was like, oh, OK. So now we're on a camping trip together. And we like-- By the way, how would you-- How would you trust again? Bekeene. How would you-- Little-- She was wearing a bekeene. And a summer dress. Like, you know, just like one of those thin little things you put around. Yeah. So looking fine is how Brazilian that gives you any ideas. So yeah. So she's just like-- she's rocking it hard. And yeah, she's super-- and in turn to alley, I mean, she's like professional and smart and reads. And I'm just like, OK, like, all right. So we talk for like 10 minutes, 15. And I go, you know, I'll go do my thing. We link back up down at the beach later. And now we're getting to time where all going-- And she's like, oh, I'm heading back to the campsite or whatever. I'm going to go shower. And maybe we'll catch up after I'm like, OK, yeah, I'll go do that. And so we exchange numbers. I think she maybe even she asked for my number. I was like, OK, exchange numbers. And then maybe a little bit later, I texted her. And I was like, hey, what do you think about finding like a cool place to watch the sunset? And she's like, oh, yeah, that sounds good. And like, all right, things are going well. So I go back. We hang out at the campsite for a bit. And again, there's like 20 plus people. And then I was like-- and I was kind of like a-- not in my head, but I was kind of like, this would be a little awkward, you know, whatever. It's just like me and her. Like, we just met. Now we're going to like run away from the group and like get in the camper van. I rented and go to this lighthouse or what I felt like kind of compelled to like ask people, like, hey, we're going to maybe go to do want to get a group together. And they're like, well, we're waiting. They're going to bring a cake for this person's birthday. And this, I'm like, oh, and I'm just-- then we just snuck out. I'm like, all right, perfect. We just dipped out and went to this lighthouse. I mean, it was just the most romantic. And so literally, it's two hours later. We're holding hands down the beach. And like, and this just like ultimate romantic situation. And yeah, and you know, six weeks later, we're still talking and hanging out. So you approach this beautiful Brazilian woman. She's in a bikini. She's stunning. And the fancy, amazing line you said again was for your opener was, you haven't moved much. Tim, most more than most than our ones. that was maybe more an author, like fuck it, you know. - The most men think flirting, and most men think flirting approaching is about clever lines. It's about saying one simple thing, committing to it and starting a conversation that can lead to six weeks later. You're still getting together with her. You too can date a gorgeous bikini Brazilian woman. - Yeah, you can. - Yeah. - Well, I'll tell you this, this is an interesting, like, well fun cultural fact, 'cause again, where I'm at now, it's just people from all over the world. So I've actually been learning a lot living here about all sorts of different cultures and talking to women here and their experience. And so apparently Brazilian guys, they don't give a fuck. Like they will go, like approaching is not an issue for them, maybe to a fault, right? So that's more in their culture. They'll go, "Hey, baby, like whatever." Like almost to a point where it could be off-putting. And so for like a, there's just like so used to it, but then they come here to like a Western country. And apparently the Australian guys here will not do that. They will never approach. They don't go by you a drink. They don't show interest. And so then it's like the other, like the opposite, where they kind of want that from a different type of guy. So then when you do it as like a Western, or just a gringo, which is say, like that really impresses them. 'Cause even not just the Brazilian group, but like a lot of the women are experiencing. So so many of them say what you say, which is like they want to be approached. And they're craving it. So when I did that with her, like I think she like immediately was kind of was hooked. - Mm. - You know, like I, like she was, you know, kind of like what you talked about at the beginning and you're open or how to get them to that point where they can't stop thinking about you or whatever the line you use. But it just, it wasn't this feeling like, okay, I need to impress them, you know, like okay, I got their interest, but I need to try this. It was just natural. And it was a mutual vibe. And I could just tell Midway through. I'm like, this girl's like, you know, like three minutes in and she's already, and I made some joke 'cause she's like, she's a citizen here in Australia now. And I was talking about like, you know, my visa, if I'm gonna move here, I'm not a citizen resident. And I was like, oh, maybe we could just get married. And she's like, oh, yeah. And I was like, oh, I'm just kidding. And she's like, what? She was like upset. And I was like joking. Like she like almost like thought that was like romantic or funny that I said that and was almost offended. That was like, oh, I'm just kidding. I was like, maybe you're kidding. You don't wanna marry me? Yeah. So I don't know. It was just kind of one of those things where everything lined up in this like incredible way and every, it's just like the formula worked to a T. So how? Have you ever felt that you created a real spark with a woman just through your eyes? Eye contact and your overall vibe. You know, you have sort of it, if I may say, you have this kind of smoldering chill, like, you know, hot searing coals kind of vibe. I would think that women would feel, do you ever find yourself making some sparks happen not with what you say, but your voice, your eye contact? Yeah, and you know, that's something I actually struggle with was eye contact. And I didn't, it was something that was a blind spot and realized I was doing. I would like look away, you know, kind of like, I'm the beta, 'cause I look away first, you know. It's like, but yeah, there's definitely power to that, something that I need to remember to hold eye contact and not kind of act of afraid, or you know, there's sometimes, it's almost like, I think there's like levels of intimacy about it. Sometimes that intimacy could be uncomfortable of eye contact. That sustained, it's just very powerful. So sometimes it, you know, for me, it's like looking at the sun, so I kind of look away and it's just like too much, it's too direct, you know, it's just some cultural element sometimes with it. But, you know, when I was at the bar of the other eye, and this girl I actually had known before and she came and like, hit on me like two years ago, and we've like kind of been until, we never like, did anything with it, but there I ran into her again and it had been a while. And I just like, I went into that mode where I was just like, staring her in the eyes and being extremely confident. And I could just tell how powerful it was, you know, or like taken her by the arm of like, yeah, no, you're with me and like, I wanna kiss you right now. And, you know, like stuff like that and just not hesitating. And I think, you know, it applies to a lot of things, but it's like, that, see, you use some line where it's like safe as dangerous or something and dangerous as safe or risk or something like that. We're just like full commitment. If like, I'm scared to jump from one ledge to the other and I pussy foot at one and I thought like, I need to go full commitment. Right. And I think that vibe. What, yeah, what feels risky in dating and flirting is safe. And what feels safe is a risky. You know, I can, deep eye contact might feel unsafe too, might feel risky, but it's the safest smart thing to do 'cause you're committing to that laser eye contact where if you're looking away, you don't wanna be, you know, you don't wanna eye fucker. Well, she might want you to eye fucker. That might be her channel that unlocks a feeling of a rousal and passion. Now, I'm not saying right out of the gate when you approach her, but, you know, 30, 20 minutes in or maybe on a first date. Yeah, yeah, that's absolutely extremely powerful. Make them look away first. You can, if you get stuck in the friend zone, you can get out of the friend zone with your eyes and then when you look at a woman. I remember I was on a first date in Venice, California. I had approached a woman, her name is Vanessa and I got her number a night earlier. We're going on a Tuesday night date and we're sitting on a rooftop bar right on the ocean. And I don't remember anything weighty or funny or amazing, and I said that night, but I remember looking at her with this wolfish eye contact. And it was genuine. I was super aroused and turned on by her. And it was toward the end of a pretty darn good date. And toward the end of the date, she could feel me giving her the Kubrick stare maybe. And she said, you're looking at me like I'm dessert. And she meant it in a good way. Fast forward, 20, 30 minutes later, we leave the venue and walk back to my hotel, which was walkable. And she's in the hallway of my hotel. She starts unbuttoning her top in the hallway. That had never happened to me. I don't think it's happened to me since, frankly, but it never happened to me before. She was taking her order off to say, I am yours. Let's go. I'm not even gonna wait till I get in your hotel. That's the power of that wolfish eye contact. And what's happening is that you are transferring onto her your raw animal desire. And she's feeling it. And if she feels something similar for you, boom, that's just nature, baby. There's nothing wrong with that. - Yeah, that is universally the way to go, to have that, you're the fucking man. You're not like that, but yeah, you just have that level of confidence and you have that intensity toward them. And I think some guys may think that you're over committing or you're seeming kind of needy. I want you so bad, but it is. It's just a different vibe. It's just like, it's not like, I like you and I hope you like me. It's like, I'm gonna take you back to my fucking apartment. And shit's gonna go down. - Oh yeah. - You know, like having that, you know, now again. So like actually this example, that was pretty good that I was saying before, 'cause I just like, I don't know, I just went into it with her, you know, and I just, you know, it's like kind of new her whatever. And I was like, you know, you and I have unfinished business because we cross paths, but nothing ever escalated. I'm like, you and I have unfinished business. And she's like, really? I'm like, yeah, you know what I'm talking about. And you know, you just tell, she's like, you know, and then, yeah, so I grabbed her by the arm and I looked at her and I pulled her toward me. And I could tell she was a little hesitant though. She was like, in tree, but she was like, I don't know, I don't know about here. And it was something I was like, yeah, I want to, I was like, she knew I was like, yeah, I want to kiss you right now. And she's like, I don't know, not here. And I was, you know, so I backed off a little but I still kind of kept that attitude. And you know, it turned out she was like, I'm in a relationship or like, you know, she was, you know, conflicted about it. But I knew though and then at the same time that she wanted me. And I think I said to her too, I was just like, again, I wasn't like super invested in the outcome. I'm like, look, turn out like, how but I kiss you on the cheek. And she goes, that's okay. So I do it in kind of like a sexy way. And then I just stare at her in the eye and you could tell. And I was like, you like that, didn't you? What you was like, yeah. You know? (laughing) It works, if you can maintain that. Look, I mean, if you look at women's romance novels and books, that's how the guy is, or 50 shades of grades. I know what I want. I want you, I'm gonna take it, versus I want you, do you want me to? - Right. - It's like, I know you do. - In a worst case scenario, you're wrong, or they're not. And then you just kind of get out of that mode and say, okay, that's why I'm going back. - It's too sexy being just like a nice dude, and it's like, okay, they're not interested, or they're not ready, or whatever. And then I just go back to, you know, I get out of like, ethical predator mode. Let's call it. (laughing) - I love that. - I love that. - Ash-tagged, ethical predator. - I think that's, yeah, that's a thing. Yeah, you want to be an ethical predator. (laughing) - Well, there's nothing wrong with a man who has romantic sexual desire, and women have it too. I was just out with a client, I'll call him Aaron. We were approaching today in New York City. And I said, you should make no apology for your desire as a 32 year old man, single, young, virile, to walk up to a woman and say, hey, I just saw you, and I wanted to meet you. Look at her with a look of intent, not intensity, but intent. I am here to flirt with you. I'm a man, you're a woman, why wouldn't I do that? It's ethical predation. (laughing) - Yeah, I was. - And there's worlds on the floor. - What's wrong with that? - Well, there's levels to it too, right? So you do it, and that's like, I'm this confident guy. He was gonna come approach you and flirt with you. Like, I'm not gonna do what I just did to that girl. Like, at Starbucks during the day, and be like, I'm gonna take you back to my place. And, you know, it's just going down kind of thing. But, like, as it escalates, you know, it goes from the approach, and, you know, it gets, you know, it gets confident, GPG, PG-13. And eventually, just feel it out to the point where it gets rated R, and then that gets rated X, and things get really interesting. But you could keep that vibe throughout. And, you know, and there's a time to turn it on, and there's a time to, you know, pull back a little bit from it. - Right. - You know, if you could tell, they're pushing their comfort zone ahead, and it's something you teach as well. Just because they say no, doesn't mean I'm, the answer is like, actually, no in the long term. I just know then. So you don't have to go back to being this, like, pussy footed, like, oh, I'm sorry, and apologize. - Right. - But you could like, you could confidently respect them. - Yeah. - You know what I'm saying? Like, you can stay in that mode, and still pull away, and be respectful. And I think there's powerful too, 'cause then, they, 'cause you want them to still feel comfortable, right? - Right. - I feel like there's like an optimal zone of pushing the comfort zone a little bit of, like, this feels a little dangerous, but then if they, you know, but then you could pull it back, and then they feel comfortable because they see that you can read the room, and you could read them. - Yeah. You can walk up to a woman, be very direct, but g-rated and gentlemanly, and women love it. And there is a time and place to then escalate things. So, quick story. I dated a woman named Alexis many years ago, and I approached her one weekday afternoon, as she and her friend were walking out. They were leaving forever, 21. And I approached Alexis and her friend, and I said, hey, I just want to come over you and say, you're adorable, I had to meet you to Alexis, and I said hello to her friend. Got numbers, went on a first date. Fast forward to the morning after our first date, Alexis came back to my place. The date went well, she spent the night, and we're lying in bed. And she said, you know what I loved about how you approached me? It was so innocent. She used that word, it was innocent. You called me adorable. What's hilarious is she said this to me as we're naked in bed, and we had just gotten done having sex on every piece of furniture in my studio apartment. And she's telling me how much she loved the innocent way I approached her. And there's a real lesson there. You can and should approach a woman with g-rated innocence, clarity, at least in the daytime. Hey, what's up? I saw you, you're adorable. You're really cute, I had to meet you. Innocent women love it. Things can get PG and R and X later, but you start with G, and it gives women the sense of respect and kindness, social respect, but hey, there'll be a time and a place to get sexy and sexual. So my tip is approach g-rated, move toward R and X as things progress. Yeah, 100%. And you could still have that like, we'll call it the EP mindset. I have a cold brother. (laughing) That's a cold-hunter.com. Nobody steal it. I just want to go daddy, it's mine. Yeah, I'll let you take it. Couple of final things here, we can wrap up. I'd love if you have any lessons you learned of like, oh man, gosh, Connell, I used to make this flirting mistake on a date. I used to say or do the wrong thing. What's a big lesson you've learned? And you've since, you've since righted the wrong, you've corrected it. But what's a flirting or dating mistake you used to make? And you have long since corrected it. Yeah, I think we touched on it a bit. I think a big one was expression of interest and intent. Making sure it's romantic. I had this, just like a quick start, I had this happen where girl, another South American girl and bikini with a little beach shawl, eating some ice cream, went up to her and said something like you're making me jealous or something, it looks really good or whatever. We have a great conversation, she's a chef, I love cooking, I sometimes like cooking videos, she does too. So I'm like, oh my god, we're vibing, I get her number and we're like, have a plan to make a cooking video. Right, and then I started being a little more flirtatious though in the text and maybe I didn't do it enough. And then she acted surprised when it became clear that I wanted it to be a date. And she even said, oh, I thought we were just doing this as friends, like, oh, I have a boyfriend or something. And I was just crushed, I don't know if that's the right word but I was definitely thrown off. I mean, I think there's maybe some fault on her end because it's like, come on, we're freaking obvious but I guess it wasn't enough. And I should, and I really process why should have done that. So I think that's a big one is being very clear and I had that happen again or maybe I wasn't aware of one hour with a girl and maybe she wasn't as clear until I felt more comfortable in the texting of it. But I need to do it in the moment and remember that because it does go well. So I think not being afraid to show intent at that stage and throughout is probably the one of the biggest ones that I keep in mind outside of them, many other lessons. - Maybe the two most important words in flirting with women is, or are, I want, I want to take you on a date. I want, I wanted to meet you. I want to see you again. I've had a great time with you. I want to have a drink with you in my place. I want you to spend the night. I want, there's something really powerful about a man telling a woman what he wants and telling her why he wants her as long as it is obviously consensual and ethical. But man, that's really powerful to women. Most men, yeah, I would say most men are afraid to say, here's what I want. I want you. And a lot of women are like, why won't a guy come up and just put it out there? And yeah, those are the two sexiest words. Just say, here's what I want. I want you. - Totally agree. Yeah, that absolutely has kind of going back to the theme of how to get them hooked or to not stop thinking about you. It is that, you know, that I'll place into that vibe, you know, the EP, this is what I want. I want you. Yeah, one more question. So I'm sober, you know, I haven't drank in many years. And so sometimes I'm self-conscious about that because it is so popular or common in dating. What are your thoughts on that? - Own it. Sober as sexy. You just want to mention it before you meet in case she feels weird being the only one drinking. But you may as well own it 'cause it's really hard to hide sobriety when you're sipping a Shirley Temple through a Swerley straw. It's really tough to do. So sometimes I notice I fall into interview mode on first dates. Do you think that's something I should stop doing? - I don't know. What do you think? How was your weekend? What do you do, by the way? Do you have siblings? When did you last cry, Evan? Who killed JFK? Our birds, robots. Why are plants so chill? Where were you on the night of January 14th, 2014? And does Wyoming even actually exist? I have more questions. questions for you or do you want to just answer those? Anyway Evan, thank you so much for again being my unofficial cohost here on Not a Good a Girlfriend. And you and I will talk later. We're going to create the ethical, what was it? EthicalPredator.com. I think we can be correct. Let's do like a, we'll do a guidebook. What's co-write a guidebook? A medical predator. Ethical predator. What would be the tagline of that? Oh man, the ethical predator. How to make women, how to be irresistible to women. Right. How do be irresistible to women with consent, whether they like it or not. Yeah, and then there's got to be some kind of wolf. There's got to be some kind of wolf in the cover. Yeah. Right. And then there's a wolf man. Just like drool. Like this looks like a rabbit wolf. But it's like nice too. Well, it's also like a gentleman and it's like passing like how holding roses or something. Exactly. It's like a, a, a, a, where wolf and how about a where wolf and a tuxedo? We're in a, yeah, yeah, where will my, my, my, tuxedo, chivalrous. I'm trying to get my girlfriend to watch one of my favorite movies ever, American Werewolf and London, which is about a werewolf with a heart of gold. So anyway, anyway, thanks for being here. And by the way, thank you for listening slash watching. And if you would like to find out how my dating coaching works and how you too can be an ethical predator. Go to dating transformation dot com or ethical predator. No, just kidding. Just kidding. Yeah, good at dating transformation dot com and you can book a call to talk with me or somebody on my team and find out how this approaching dating flirting things flirting thing works with Conel Bear. Anyway, dating transformation dot com. Thanks again for being here.

Podcast Summary

Key Points:

  1. Women rarely remember witty opening lines; they remember eye contact, good posture, and a confident vibe that says you belong.
  2. Overcoming approach anxiety often requires taking action despite mental blocks, using techniques like wingman challenges or accountability (e.g., giving a friend $100 to force approaches).
  3. The most effective openers are simple and authentic—like “You’re really cute”—rather than rehearsed or clever lines.
  4. The conversation itself matters more than the first line; how you make a woman feel (fun, comfortable, interested) is what she remembers.
  5. Playing to win means pushing past safety to show romantic intent (e.g., giving a compliment) and aiming for a number or date, not just a friendly chat.

Summary:

In this podcast episode, dating coach Connell Barrett and his client Evan discuss how to flirt effectively so a woman can’t stop thinking about you. They emphasize that women rarely remember witty opening lines; instead, they recall eye contact, good posture, and a confident vibe that signals belonging. Evan shares a recent experience where he struggled with approach anxiety at a birthday party, but used a friend’s challenge to break the ice and build momentum.

Connell reinforces that the bar for a good opener is low—simple, authentic statements like “You’re really cute” work powerfully. He recounts a Barnes & Noble encounter where saying just that led to a date. Both highlight that the conversation itself, not the first line, is what matters; women remember how you made them feel.

Evan notes the importance of playing to win—showing romantic intent by giving compliments and pushing for numbers or dates, rather than playing it safe. They conclude that authenticity and courage outweigh cleverness, and that taking imperfect action beats overthinking.

FAQs

Women often remember eye contact, good posture, and your overall vibe more than any witty line. They recall how you made them feel, not the exact words you said.

Use accountability with a wingman, like giving them $100 to keep if you don't approach someone they point out. Alternatively, just speak your authentic thoughts, such as 'You're really cute,' to lower the pressure.

You don't need a perfect line. Say something relevant to the situation, like 'Is this your new office?' if she's working at a beach, or simply 'Hey, you're cute. I wanted to meet you.' The conversation matters more than the opener.

Get out of your head by taking immediate action, even if it's uncomfortable. Use a mission from a friend or just walk up and say what you're thinking and feeling to break the cycle.

Even if it doesn't lead to a date, it's still a win because you practiced and built momentum. Focus on the process, not the outcome, and remember that many fears about rejection are not true.

Focus on making her feel good in the moment through confident eye contact, good posture, and genuine conversation. The emotional connection is what she'll remember, not any specific line.

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