If you’re stuck in the Friend Zone with women, dating coach Connell Barrett has been there. He didn’t just live in the Friend Zone—he owned real estate there.
But he learned how to escape. And in this special LIVE COACHING episode with his client, Chris, Connell will give you a practical plan to stop getting “friend zoned” and start igniting sparks with women you’re interested in.
That’s right! This episode is the second-best thing to working with a great dating coach, because you get to listen in and use ALL of the tips.
If you’re like Chris, you’ve had his struggles: He could get dates, but women kept saying the same thing after a date or two: “You’re a nice guy, but I’m not feeling a connection. But we can be friends.”
In this episode, Connell gives Chris—and you—a simple plan that helped Chris go from hearing “Let’s be friends” to “Let’s make out!”
These tips transformed his dating life, and they can do the same for you.
Connell helped Chris go from the friend zone to fun, flirty dates that make sparks fly. And you can fix the friend zone, too! Listen now.
For a Free Strategy Call with Connell, to Learn How to Attract Your Dream Relationship:
Get Connell’s Bestselling Dating Guide for men, “Dating Sucks but You Don’t,” your step-by-step guide on how to get a girlfriend:
00:03:05 The three social contexts
00:05:46 The man-to-woman communication
00:10:01 Book your free call today with Connell Barrett
00:11:42 Coaching Chris
00:17:05 Chris’ typical dates
00:21:02 The seven essentials of great dates
00:33:47 Get the amazing book of Connell, “Dating Sucks, But You Don’t”
00:35:12 Continuation in coaching Chris
00:37:09 Chris on his man-to-woman communication
00:45:49 How to be yourself in dating
00:47:58 The four escalators
00:46:58 Connell’s tips to Chris
Connell Barrett: Yeah. The thing about confidence is a lot of guys think I want confidence, but first, they need courage. Basically, courage is the currency that buys you confidence. You gotta earn that shit. All right, here we go. We're back. Another episode of Dating Transformation. The podcast sounds like a movie when I say it like that. I am your host dating coach Connell Barrett. I am here to help you gain confidence, learn to flirt, and attract your dream girlfriend and do this all while being truly authentic. No pickup artist B.S. and you're going to love this episode. This is the first kind of episode we've done. This way you're going to be able to be a fly on the wall as I do a coaching call, a genuine live real-time coaching call with my client Chris. Not his real name, by the way. And Chris and I, you're going to be able to hear me, Coach Chris, and help him basically make sparks fly, make sparks happen on dates because he's been dealing with some friend zone issues. He's having nice, pleasant dates, but women just aren't wanting to see him. So by the time you're done listening to this, you're going to have all my best tips that I give to Chris. You'll be able to use some of the same concepts on your next date so that you can make sparks fly. Okay, so now to that point, let's make this a theme episode because what I want to do right now in the little four or five-minute opening here is to tell you about the closest thing there is to a secret weapon in dating. And look, the bottom line is, I won't bullshit you. Look, I'm a marketer when I'm not being a dating coach, so I'll just be straight with you, though. There is not. There are no magic bullets in this area. No instant quick fixes, no Band-Aids. I mean, not really. Don't get me wrong, there are some really good, simple tips that can completely uplevel you in a certain area, but there are really no quick fixes. But the closest thing there is to a secret weapon. The closest thing there is to a quick fix is what's called man-to-woman communication. This idea of getting on a channel, the same channel as the woman you're talking to, and being able to talk to her like a man talks to a woman as opposed to the way a friend talks to a friend. So I'm going to give you a quick overview of man-to-woman communication and give you one or two quick examples. And there are a lot, lot, a lot more examples in my book. But let me just give you a quick lesson in how to be the man to woman, because this is what's going to help you make sparks fly, get out of that friend zone and make some wonderful things happen. So think of it like this. If you think about it, there are really only three kinds of social contexts you have other than you with your family, right? I'm excluding your family relatives. Every other social interaction you have falls into one of three buckets. The first one is what's called, let's call it man to woman. In other words, you are a woman. Romance is possible in a man-to-woman context. The second social context is friend, a friend. You and your friends. You and people who are either friends or acquaintances may be moving toward friendship. And then the third social context is business slash professional. So, for example, you talk to your boss, and he's giving you your performance review, and that's a business professional context. You're buying jeans. The girl comes over and says, Hey, can I help you with those jeans? It's a professional context. A friend, a friend you're having drinks with your friend having a couple of beers at the end of a long day. That's a friend of a friend. And then, of course, man to woman is flirting. Basically, think of man-to-woman as a turbocharged form of flirting. It's you strumming a woman's romantic strings by being flirtatious, projecting an authentic but masculine energy, and letting her feminine side come out. It's a clear man-to-woman like Eve. I'm sure you've seen a man and a woman on a really good date that's going well. They're all over each other. They're. They're flirting. She's twirling her hair. He's taking up space. Being a man, my friend, is man-to-woman communication. So. Again, the closest thing there is to a secret weapon or a magic bullet in this concert or in this world of improving your dating life is switching out of the friend-of-friend frame into the man-to-woman frame. So think of man-to-woman communication as a lens. And you want this lens to refract your true authentic self in every area of dating, texting, first dates, and approaching phone dates. Basically, every conversation you have with a woman, at least a woman you're attracted to, is going to be man-to-woman. Okay, here's where you get into trouble. Here's where you can really hurt yourself and not even know it. This is probably the biggest mistake. Maybe the biggest mistake guys make without knowing it is they don't they aren't even aware of these contexts. And you go on a date or you approach a woman, and instead of being the man to woman, instead of being flirtatious, instead of taking risks, you are a lot safer. You're nice, you're friendly. But you're not putting romantic cards on the table. You're not telling her she's sexy. You're not being vulnerable. Maybe you're being very logical and not more emotional. Slash flirtatious. So the reason is if you go on dates or if you talk to women and it goes fine, but they're just not into you, or they say, Hey, I had a good time, but man, let's just be friends. Or I'm not really feeling the connection. What she's really saying to you probably is you got on the friend-of-friend wavelength and I wanted you to get on the man-to-woman wavelength. So big is the closest thing I have to a game changer. An instant game changer in your dating life. Other than being that authentic, radically authentic man is first just understanding what man-to-woman communication is and also learning how to speak to women through that lens. Okay. I'll give you one quick example and then we'll do the coaching. Call it with Chris. I had a client who came to me, this guy Trevor. Trevor, date after date after date. He was told, hey, I'm just not into you. Trevor was being very safe, not taking risks, not teasing his dates. He was just kind of just being like, Oh, hey, great. Tell me more about you. Okay, great. Where do you go to school? Okay, great. Not being. Not letting go and flirting. I coached Trevor up. He has his first date as my client, and he has a first date with this really awesome woman named Becca who was a chef or is a chef and a really intelligent, really witty, gorgeous brunette. And just real a real ten out of ten in all the ways a woman can be a ten out of ten. She shows up for their date and he's immediately teasing and joking about it. I forget what it was, but he's cracking jokes. He's teasing her gently about the fact that she was late. At one point she's talking about something and he changes the subject. He's like, You know, that's great. I'm sure your story about makeup is great, but listen to what happened to me today. He sort of took control of the date in a good win-win way. He also told her that he found her really cool and he found certain things sexy about her. He busted her balls a little bit. Halfway through the date, Becca crawls on Trevor's lap and sits on his lap, and they're making out. And everybody in the bar, Trevor tells me, is looking at them like, Hey, dudes, get a room. What the hell? And their second date was a couple of massages that she set up. She said, Hey, this should be our second date. Not a bad second date. Trevor is the same guy for and after. The difference is he made that shift from being a man to a woman. Okay, so think of man to woman as the closest thing there is to that secret weapon, to making sparks fly. And there's a whole chapter in my book all about how to be a man to a woman. WOMAN Dozens and dozens of specific techniques and tools. If you want to get a whole list of all the different ways to be a man to a woman. Anyway, that's in my book Dating Sucks. But you don't. Speaking of making sparks fly. Let's go to Chris. You're going to start with a coaching session. This is a legitimate, authentic, real coaching session. You're going to be eavesdropping on me helping Chris take his dates to the next level and get in that man-to-woman zone. And let's go. To me coaching Chris. Hope you enjoy it. We'll be right back.
I'm going to read your mind. Ready? I'll bet that you would love to confidently approach women, get great matches on dating apps, flirt with charm, and attract your dream girlfriend. Right. But fear keeps you from approaching. You're not sure how to flirt. You struggle with the apps. And desirable women just don't seem into you. Well, I have great news. Dating coach Connell Barrett can help. He's guided thousands of men like you to more confidence and helped them attract their dream girlfriends. So book a free strategy. Call today to see if Connell's coaching is right for you on your call. Connell or a team member will give you personalized advice to help you have more confidence, more dates, and more fun. Oh, and you'll be dating women as your best self. A charming gentleman. That's because Connell does not teach creepy Pick-Up artist tricks. He unlocks your most confident self so you can make authentic romantic connections. Your next steps. Book your free call today for a dating transformation that comes forward, slash contact, and grab a time that works for you. Then you'll be on your way to more confidence, better results, and attracting bright, beautiful women. Oh, so, you know, soon Connell will stop taking on new clients. So book a call today while you still can go to a dating transformation that comes forward, slash contact and transform your love life. Bye.
Connell Barrett: Hey, Chris. What's going on, man? Happy afternoon.
Chris: Hey. Yeah. Happy afternoon. Afternoon to you too. How are you doing?
Connell Barrett: I'm good. I'm good. It's a good Friday. Happy to be chatting with you, so. Yeah, let's get right to it. According to what you told me in sort of a little preliminary conversation, an email exchange we had. It sounds like you got a couple of things that aren't working in your dating life in the vicinity of friendzone date's not going the way you want. Tell me a little bit about what's been happening and what's not been working.
Chris: Yeah, so I'd say there are kind of two things. I'd say it's, you know, meeting more girls, meeting a higher volume of girls to go on more first dates is part of the problem. But also I'd say just kind of like turning the first date, second dates into, you know, three or four or five dates and eventually into a relationship is probably kind of the two big problems I've been having.
Connell Barrett: Okay. Got it. Give me a little bit of data here. Ballpark numbers are fine. Let's look at the last, I don't know, three months of your life. Ballpark number. How many girls have you met? Met up for one or more dates?
Chris: Probably. Maybe three or four of those.
Connell Barrett: Three or four. How many of those dates did you fill out? She was into me and I was into her. Things were going really well.
Chris: I'd say the first date. Pretty much all of them.
Connell Barrett: Okay. And then so the chokehold here is would you say it's date number to date number three sometimes?
Chris: Right around then. Yeah. The number two or three.
Connell Barrett: Do me a favor if you can tell me a story or an anecdote or just like a specific moment where you were out on that second date or third date and the first one had gone well, which it sounds like most of them are. But then you felt it just sort of, you know, you ran out of things to say or maybe you kept the conversation going, but you just felt like that spark was diminishing. If you could paint a little bit of a picture for me so I can kind of put myself with you almost like I can, so I can kind of try to see what might be happening.
Chris: Yeah. So I'd say just try to think of like one example here, like I went on a date with a girl a couple of years ago now, but we're on a couple of dates, and had a class together. It was going really well for a second date. We're hanging out a lot and then I thought our third date was like a party and I could just kind of tell maybe that day it seemed like she was texting me a little bit weirder. That seemed like it was kind of the same chemistry that we had had. And then I could just kind of tell the whole night she just was kind of a little distant, maybe not as conversational, just in a little bit, kind of off. And then like the next day kind of just ghosted me and never heard from her again. So like that kind of thing, I'd say usually, you know, I guess that's kind of an example of the kind of other problems, I guess, but where it seems like it goes really well and maybe, you know, maybe there are some signs I'm not picking up on necessarily, but it seems like it is going generally very well. I definitely feel like there are signs of attraction and I'm not turning that into something that builds up past a third date or it seems like after that point they just don't seem interested anymore.
Connell Barrett: Got it. So we're basically talking about like the third date friend zone. The third date, while fair to say.
Chris: I'd say yeah. And you know, not everyone is exactly on the third date, obviously, but, you know, that's kind of, I think in general where it seems to go wrong.
Connell Barrett: Okay. A couple of other questions here. And by the way, you're the only one to get exact here, but you're in your twenties. You're a young guy, you're single, and you're out there meeting girls, but you're also looking. The goal here is a relationship. Is that right? You're looking for a girlfriend eventually.
Chris: Yeah, it's definitely. That's the goal.
Connell Barrett: Okay. Got it. So it's probably because I don't want to put words in your mouth, but is it frustrating? Does it make you get a little bit like, oh, what am I doing wrong? Especially when it seems to start well on the first or second date and then it sounds like you're losing momentum. So is that frustrating? What does that feel like when that happens?
Chris: Yeah, frustrating is exactly right. Like it's you know, it seems like it's going well. It seems like, you know, I mean if people are really into me and I'm really into them and it feels like it's heading that direction where it's going to turn into a relationship. And then when it just doesn't and it repeatedly happens, it's very frustrating because the ultimate goal is to be in a relationship with someone that, you know, we make each other really happy. So.
Connell Barrett: Yeah, okay. Got it. Have you ever thought of just giving up on dating and just going with an inflatable woman?
Chris: No, not yet.
Connell Barrett: Oh, okay.
Chris: Well, all right. Would be a lot easier.
Connell Barrett: I guess we should continue. I was just going to send you an inflatable woman. We could end this right now, but. Okay, let's go a little bit deeper. By the way, I've totally been in your shoes. The reason I became a dating coach was I had to first solve all of these problems myself. FriendZone dates one through three basically were a big sticking point for me. So I. I've been in your shoes and yeah, I can suck when you're like, Oh, wow, we had a great connection. That seemed really great. She was into me, I was into her. And then maybe one or maybe one or two dates later, she just goes quiet or she says, Hey, you seem awesome. You've probably gotten to seem great, but let's just be friends kind of text, right? Mhm. Yeah. Yeah. Those are fun. I'd rather get a text message from my doctor saying we have to talk than that kind of message from a girl. So I have been there. A couple more questions for you and then we'll get into some tips and go a little deeper and try to figure out what the chokehold is. So tell me a little bit about your typical first date. What things do you talk about? Where do you go with these girls? In other words, tell me a little bit about the dates that seem to be going well.
Chris: Yeah. So it's typically like we'll go to dinner, maybe dinner and a movie or something like that. So I'd say that's kind of like my go-to first date. And I'd say, you know, the conversation generally I think flows pretty well. I wouldn't say it's super flirty or anything, but it definitely feels like there's chemistry and attraction. And, you know, I think it kind of ranges from a lot of stuff typically, you know, be things from things we have going on in our lives to, you know, kind of how we grew up and, you know, just past experience we've had. But it's, it's, you know, even like shared interests, you know, things like music and TV shows and movies, that kind of thing. Okay. So that's kind of where the conversation usually is.
Connell Barrett: So first dates, typically dinner in a movie. What about second dates? Typically, where would a typical second date be like?
Chris: Yeah, it really depends, I'd say. It's just kind of more situational than anything. Like what kind of seems like a good opportunity to take someone on a date to so as it might be, I don't know, like ice skating, it might be going to a concert. It might be dinner again. I think it really varies. I don't think I've been consistent. This is what I usually do for a second date. Yeah.
Connell Barrett: Okay, got it. So a quick tip. I'm not saying this is going to be the game-changer, but here's a tip. I'm not a huge fan of first dates which are dinner and movies. The reason is that typically with a dinner first date, you're sitting across from her as opposed to next to her. It can be distracting to look, I don't want anybody to have to hear the mouth noises I make when I'm eating. I would much rather be able to have just a drink with her or do an activity. Activity dates are great for a first date because it gives you something to do and also talks about that thing, but without feeling like you might be sort of stuck there having dinner plus dinner, first dates get expensive as well. So this is just more of a side. Side note tip. I don't think this is not the reason why the third-date friend zone is happening, but I would say for first dates I would avoid dinners. Think, think first date drinks or first date activities like ice skating or roller skating or ping pong Jenga smackdown events. Those are always fun to do because that way you get to talk about the thing and each other. Whereas dinner can feel like you're just sort of, you know, stuck sitting across each other also. And we're going to get into this in a second. I am not crazy about dinner. Plus, if you're going to a movie, you're not talking about each other. And if you're at dinner, okay, you'll be able to talk about each other. But it can feel more like, I don't know, it can feel a little bit more like a friendly conversation as opposed to two people getting closer romantically. So just a general tip as I would try to. Plus, dinners are just getting expensive. So if you want to get food and the day's going well, fair enough, you can get up, you can get pizza, you can get something maybe smaller, quicker, but for a first date, I recommend something like drinks and see how it goes. And ideally, sit next to her at whatever place you go physically next to her side by side if possible like a couple of stools up at the bar. A bar, a place that has. Having a couch, chairs, and sofa, where you're able to be next to each other lets you, if you both are comfortable doing this, be a bit physically expressive, and able to touch each other. It's a date, so you can do things like a high-five, tap around the shoulder or she can touch your back. Physical expressiveness is one of the ways we escalate from friends to romantic partners to eventually boyfriend girlfriends. So that makes sense. Mm-hmm.
Chris: Yeah, definitely.
Connell Barrett: And that's harder to do when you're sitting across from each other at a dinner table. Mm-hmm. So just sort of a side tip there. Okay. So let me give you a list here. I'm going to give you a list of what I call the seven essentials of great dates. These are the seven most important things that a man wants to do on a first date. And what I like to do is just run through all seven real quick, and then I want to find out how many of these, if any, you feel like you're not doing or that you could do better. Because when you're in the friend zone or when you're hitting that wall after one or two dates, or in this case, maybe it's roughly the third date. It's good to just look at a quick checklist and say, okay, am I doing these essentials reasonably well? Okay, so here we go. Here are the seven essentials of great dates. And when I say great dates, I basically say dates one through three. Essential number one is to be authentic but amplified. In other words, be yourself. As you might know, you read. You read my book, right, Chris?
Chris: Yeah, I did.
Connell Barrett: Yeah. So my book is my coaching. My book is all about show women that authentic self, be the real you because women are going to like you for you. And that's going to make you your most confident, your most attractive. So essential number one of the great dates is to be authentic but amplified. My coach used to call it beat, be pointy, be 5% bigger than you would be if you were just hanging out on your couch eating Cheetos with your guy friends. Right. So it's not. It's not about putting on a persona. It's about amplifying who you are. Just being a bit more expressive, a bit more honest. Talking a little bit louder. Yeah, I call that amplifying the authentic you. So that's number one, be authentic, but amplified. Number two is lead. Be a man with a plan. Choose the venue or, you know, choose it and then run it by her. Pick the thing that you're going to do on the first date. Lead the conversation. Uh, choose the night, the activity. Or at least be the one presenting these options to your date. Because women love a man with a plan. And leading on a date also includes leading in the conversation, and keeping the conversation in areas that are conducive and good to date. In other words, noticing in the middle of a date, oh, gosh, we've been talking about politics and the weather for the last 20 minutes. No way. I got to change this. And then changing the topic to something more fun. You know, each other's hobbies or travel or what have you. So number two is lead. Be a man with a plan. Number three is to think fun and flirty, early and then real and vulnerable late. I mean that both in any given date, but also the arc of, say, the first three dates. Early on. The girl you're on a date with wants to feel. Hey, he's fine. He's flirting with me. It's light, it's playful at the same time as that date and as those three dates. Branch out over the course of three dates or so. She also wants to feel, Oh, I'm also seeing the real guy, the real vulnerable guy. So that might mean 15 minutes into the date. You're teasing and joking and just having fun. And then 2 hours later. You're opening up about your goals, and what you're going to do in your career next. Telling stories from your childhood. She's opening up about who she is. Stories from her life. You're both being more real and vulnerable, and this helps create a deeper sense of connection. So that's number three. Fun and flirty. Early. More real and vulnerable. Late. Number four, the fourth essential of a great deed is the 2 Ps. Actually, 3 Ps. Be positive, playful, and present. Positive just means hey, bring a good vibe to the date. If you're. Boss just fired you or your dog is sick. I'm sorry, but we want to bring positivity to a date. Playfulness is having a little fun. A light, fun, playful vibe is what women want on dates. And then present is just really about active listening, really listening to what she's saying and also listening to yourself and being really present with her because that is actually going to unlock and awaken you at your most sort of present, witty, cool self. That's number four. Number five is to seek to connect, not to attract. A girl who's on a date with you, Chris, or anybody out there? You, the listener, if she's on a date with you, she's already attracted to you. But if she's putting you in the friend zone, she's not feeling connected to you. You're attractive already. You don't need to work on the attraction. We need to work on the connection. So, for example, when a guy is accidentally focused on attraction, sometimes he can try too hard to impress her. Instead of seeking to find commonalities with her, which is more about connection or looking at different areas of life where you feel the same way. Liking the same things, having the same. Like you're. You're. You're a music lover, right? You're a musician. Mm-hmm. Yeah. So maybe on a date. I'm not saying you're doing this, but I could see a guy trying to impress his date by saying, Oh, yeah, I play this instrument and I'm in this band, as opposed to sharing his passion for music with her and then letting her share her passion for music. And all of a sudden you've got two people connecting about the same thing as opposed to trying to impress her about one of the things you do. So we want to think of connection, not attraction. Number six of the seven essential great dates, the essentials of great dates is flirting. Help. Help her to feel sexy. Compliment her. Uh, tell her how great she looks. Or tell her something about her is sexy. One of my favorite tips I give men is. Don't tell her she's sexy because of her eyes or her body or her beauty. Although, hopefully, she is. Maybe she is. I hope she is. Tell her something about her that is very attractive and sexy. A trait. A quality. Her wit, her mind, her presence. Her silly sense of humor. A woman. A woman who's attractive for the most part. She knows she's attractive. But when you tell her that you find something sexy about her, that's a great way to flirt. And also let her know that you see her deeper. And that helps with connection. And the number seven, the seventh essential of a great date is. I call it, go for it. Basically, take a risk to win on most dates. There's some moment of truth when you're feeling fear about something and it's time to try something a little bit bold. It might be going for that first kiss. It might be saying a really true, authentic, vulnerable thought. Like, wow, you know what, Katie? You're the coolest girl I've met in months, and I just had to share that with you instead of hanging back and playing it cool, which I would not do. Maybe it's for hand-holding. Maybe it's just asking her out. It's just doing something. There's usually some moment in most states where fear gets in the way a little bit and you're afraid to go for it, whatever it is. And when in doubt, we want to play to win, as opposed to playing, not to lose. So a super quick recap of all seven. Number one, be authentic, but amplified. Number two, lead. Be a man with a plan. Number three, fun and flirty, early, real and vulnerable. Late. Number four, be positive and playful, and present. Number five, seek to connect, not attract. Number six flirts. Help her feel sexy. And the number seven? Go for it. Take a risk. Play to win when those moments arise. Now looking at this whole list, just give me a quick, quick gut reaction. Which of these do you feel like? Oh, I'm definitely doing very well, but maybe I'm not doing a couple of these others the way I need to. What are your thoughts, Chris?
Chris: Yeah, I don't know if there's any that I've really felt like I've mastered or had like 100% down. There are definitely some that I feel better about than others. I'd say, like, you know, being positive, playful, or present, I feel pretty good about that. I think kind of fun, fun and flirty, early being more authentic, vulnerable and something I do, I could kind of be a little bit more a little bit better about it, I guess. I think flirting is definitely the biggest thing that I like, I just am not necessarily good at. Like, I can give the girl a compliment, but like, how do you kind of maybe build this cool connection in a way that's kind of appropriate on a first date or second date or third date? I'd say that's something I need to kind of just work on. Okay. I'd say seeking to connect as opposed to attract. I think it's something I've definitely gotten better at over the last maybe a couple of years, but could still be a little bit better with, I'd say the kind of the first point you mentioned authentically and kind of amplified. I feel like I'm usually very authentic on a date that's maybe just not quite amplified enough. So I think maybe that could be something to look at. And then the last thing kind of leading on dates, I feel like generally, I do a decent job leading. I was actually going to ask you though, like what's kind of the balance between leading on a date and, you know, suggesting ideas and kind of taking charge of here's ideas and leading the conversation and all that while still making it so sure that it's like something that she wants to do is something that is kind of like her ideal date, you know because I feel like I might throw out an idea or something and it's like I want to make sure that she would actually find that really fun as opposed to something that she would hate. And she's kind of doing it for an hour because I'm really confident.
Connell Barrett: Absolutely this as opposed to here's what we're doing. Woman And then like a caveman dragging her by the hair to the next thing. No, obviously you don't want to do that. I love the word. Let's. Here's a great word to use on dates or even before even when setting up the date. You could say, hey, I have a great idea. Let's. Dot, dot, dot. Go to the cool margarita bar I mentioned or let's go ice skating. Well, let's say you're on a first or second date. You want to go somewhere else or do you think another spot would be really fun? You would say, Hey, I have an idea. I know this really great, cool little jazz bar. Let's finish our drinks and head over there. Is that cool with you? And then you can always follow it with is that okay with you? Because you do want to show that empathy for her and check in with her to make sure you're not leading towards something that she's not into, because we don't want to do that. But generally, women are going to say, wow, this guy's got a plan. And if it is a fun idea. More often than not, they're going to notice that you're leading, you're taking the lead you're planning. And within reason, they'll say, Cool, you lead, I'll follow. It's kind of like a dance. Men lead mainly. The dance women follow in the dance, literally on the dance floor. And if she doesn't want to do the thing, certainly totally find it mentioned that another way to do this, Chris, is like, I used to do this a lot. I would. Let's say you're texting with a girl setting up the date and you. But you want to choose something that you think she'll be into. So you might say a question for you. Are you more of a classy cocktail lounge kind of girl or more of a fun, dirty dove bar kind of woman? Give her a simple, fun, binary choice either. Because you know what? If she's not into fancy cocktail lounges, the last thing she's going to want to do is to have you overly assertively lead that you want this information to know, oh, she's more into dove bars. Cool. I know. A fun little cool Dove bar we can go to and then you and then you plan it from there. So it makes sense.
Chris: Yeah, definitely.
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Connell Barrett: Or Same with you or it doesn't even have to be drinks related. It could just be. Hey, I got a couple of great ideas for our date. Our first date or our second date? Uh, you could send two or three options. I used to send them as fun little pop quizzes via text. Right. Hey, Angela, pop quiz for our second date. I'm thinking we should, a, go play Jenga B, rooftop drinks C and maybe I, I don't know, crack a joke for the third one or C, insert your idea here, and there you are, bringing her into it and giving her the option of basically collaborating with you, planning it together, but you're still taking the lead on the planning of it. So these are all options that you could do. Makes sense.
Chris: Yeah, definitely. Yeah, that sounds good.
Connell Barrett: And so it sounds like, of these seven, I think the biggest one you said, oh, maybe I'm I could do this better or focus on a more is number six flirting helping her feel sexy. Yeah.
Chris: Yeah, I'd say so.
Connell Barrett: Okay. So you remember the Man to woman communication chapter in my book. So yeah, I mean, in the book Dating sucks, but you don't. There's a whole chapter about the art of essentially creating, what I call man-to-woman communication, those sparks on a date. And you don't need to do a lot of it necessarily on a date because remember, she's already on a date with you. The context is pretty much pre-framed. It's clear that you're out together. At the same time, you want to sort of lean into that context and just allow yourself to flirt a little bit, maybe a lot. It depends on the dynamic. Everybody has a different chemistry and dynamic. So tell me a little bit more about how or if you've been flirting on dates, how you've been, quote, man to woman, if at all. Give me your thoughts.
Chris: Yeah, I'd say usually it's just like a compliment. Like I'd be like, hey, look really good tonight or something like that, you know, I think maybe like hand-holding or I thought my arm around or something. So I guess I should go to a movie. Like, it's really, really clear I'm around someone, so. So that happens. But yeah, typically I'm not just like, I don't know if it's just I'm a little bit not familiar with it or maybe it's just the dynamic of what I'm going out with too. It just doesn't really feel like there are maybe moments and maybe that's just because I'm not picking up on it either. So I think I'm just kind of a little uncertain about what I do. How do I kind of create a spark or kind of create a moment where it's a little bit more flirty?
Connell Barrett: Okay, got it. And what about first kisses? Are you typically going for the first kiss-on-one? On which date are you typically going for a first kiss?
Chris: Baby? More like a second date. Second or third date. Your second date.
Connell Barrett: Okay, got it. And. What about? And what? This is a big question. And you talk about a lot of things on dates, but. What kind of topics do you and your dates discuss? For the most part. Is it school? Studies? Work. Lives. Politics. How would you? Where do you spend most of your conversational topics?
Chris: I'd say mostly like lives and like interests. Like what are we doing? You know, things that are going on. Mostly, I'd say, in her life too. Like, I try to ask more questions and try to be really interested in what she has to say. Okay. I mean, obviously, I can go on a date with someone, so, I find them somewhat interesting at that point, or at least I like them. So I want to find out more about them and get to know them. And so I'd say a lot about kind of trying to learn like what she does, like trying to understand her a little bit better. But also just interesting things like movies, TV shows, music, just that kind of stuff to get a sense of who she is after some of that stuff.
Connell Barrett: And do you share a lot about yourself as well?
Chris: I try to. I think that that's maybe something a little bit better is just being consistent. I think generally I'm sharing points and I'm not just asking questions like it's an interrogation for an hour and a half, but I think they've been really consistent about offering up good things. And I'd say maybe one thing, too, that I think I could be a little bit better at is like getting something that's a little bit more like not trying to just be the natural next conversation thing or trying to do something that I can share, something that's a little bit more flirty or trying to share in a way that kind of builds a spark or builds chemistry as opposed just stating something else to keep the conversation going.
Connell Barrett: Got it. Okay. And so the next question. Just be as honest with me as you can in terms of flirtatious statements and actions. You know, telling a woman she's sexy, going for a kiss, you know, at the right time, looking at her with desire, sort of letting that sexuality come out. On a scale of 1 to 10, on your typical first date, first and the second date, one being you're a priest, ten being Barry White. I don't know the chef from South Park. Super sexy, you know. Sexy time, Virat. On a scale of 1 to 10, where do you fall on? On, say, dates one and two?
Chris: Definitely lower. And I'd say maybe like two or three or something. I think I could maybe five or three. And I think it's not like that. I like acting very friend zone, but it's also yeah, kind of don't know how to act flirty in a way that doesn't come off as kind of being a little bit creepy or presumptuous. And so I tend to just kind of play it safe. Yeah, I'd say, like, the second date is typically a lot is always, I'd say, more flirty or there's more connection on the first date. But I think the first date, it's actually not super flirty, but there's the obvious attraction of like we'd like each other, but it's not really flirty.
Connell Barrett: What is the putting on the spot here? But hey, thanks for being a game. Think back over the last few months. What is the single flirty slash sexiest thing you've said to any of your dates?
Chris: Probably something really simple, just like, Hey, look really nice tonight.
Connell Barrett: Okay, got it. Yeah. Okay, so you're saying you want to die and never get married and never have a woman in your life, basically, right?
Chris: Pretty much.
Connell Barrett: Yeah. So the inflatable woman is on her way. Her name is Trish. She's really cute. Uh, okay. So I think I definitely see a big chokehold. This might be the chokehold of the fix. If nothing else, that's something that I totally want you to go out and dial up within reason. Which are we want to. You want to. You want to lean into this frame of, hey, I'm a man, you're a woman, and I'm into you. If you are into her and I'm going to convey that in clear ways, it's not about being all sexual berry white damn girl. You look so hot tonight. But it is about. It is about feeling it a little bit more. Because just the way you said that to me, I don't know how you're saying it to these girls on your dates, but if you say, Oh, hey, you look really good tonight, even that you're not committing to it, you're not feeling it. You want to say you want to kind of look her over a little bit, not lascivious leave, but look her over and kind of give her a little when she walks in and say, damn. Wow. You look amazing tonight. I just forgot what I was going to say. Where am I? Oh, right. Sorry. I'm Chris. Right. As opposed to. You look nice tonight. Can you feel the difference between them? Oh, you look really nice tonight. And damn, you look amazing. And you're almost as sexy as me. Wow. Girl, can you feel the difference there? Just in my tone of voice and how that might feel to your date?
Chris: Oh, yeah, yeah, absolutely.
Connell Barrett: And this so much of dating connection and quote-unquote success. So much of this is an emotional game. One of my old coaches used to say that it is about transferring your emotion onto her. Like, have you ever had one? I'm sure you have. Have you ever had a really cool, attractive girl? Whether it's a date or maybe just out flirting at a party or a girl clearly makes her interest known to you. By the way, She looks at you, flutters her eyes, or just twirls her hair. Have you felt that interest conveyed to you? At least sometimes.
Chris: Oh, yeah, definitely.
Connell Barrett: How does that make you feel? I'm assuming she's a cute girl.
Chris: Yeah. I mean, it makes you feel great. Like it makes you feel like there's, like, this really cool girl's interest in you. And, like, there's a bunch of potentials, like. So something could happen, something develops from it, so. Yeah.
Connell Barrett: Right. So you want to. You want to give that same kind of energy, but of course, in the masculine context, and give women those. Those tingly feelings that women can give you when they look at you, those big eyes and that attentiveness. And so, yeah, I really think that the big chokehold here or the main one, based on what we've talked about so far, is, are these other seven essentials. I think you're somewhere in the middle of the continuum, but with the flirting, you're at maybe a two out of ten, and it is a date. And I think what's probably happening is my best guess right now, Chris, is you're a handsome guy, you're articulate, and you have a lot of value. You have that authentic value that women want. So they see on paper how awesome you are. And that's going to get you that'll probably get you a second and a third date. But what I think what's happening is they're not feeling that sense of deeper romantic connection, that sense of, oh, yeah, he's a great guy, but I'm not feeling the sexy way I want to feel. I'm not he's not, he's not helping me unlock that feeling of I'm feminine, I'm beautiful. We see it. We see the world the same way. And maybe you're having conversations where she feels an intellectual connection to you. But of course, this is dating. We want it to be a heart and romantic connection, and you don't need to do it. It's not about doing a lot of it. It's just about doing it's about making it clearer and being more upfront with that and letting her know that you're making no apologies for your desires as a man. Does that make sense?
Chris: Yeah, definitely.
Connell Barrett: Okay, cool. So let's talk about how to do this in a way that's very Chris because I don't want you to come across like somebody else or try to just say, you know, flirty, creepy things. So are you a physically expressive person when you're with your friends when you're out with your guy friends, are you slapping him on the back, high-fiving them or, you know, having a little bit of like touching back and forth, or you kind of just like hands to yourself kind of person.
Chris: Probably more hands myself. I'm not a very expressive person, I'd say in general.
Connell Barrett: Okay. But with people who you know well, with family, and friends, would you maybe give them a hug, give them a high five, punch a shoulder for your big brother, or maybe that kind of thing?
Chris: Yeah, absolutely.
Connell Barrett: Okay. Um, do you do anything like that on dates? Um.
Chris: Not generally, I'd say, you know, like, I might give someone a hug, you know, might hold hands, but, like, it's it doesn't. It doesn't feel very like a romantic, like, desire, lusty kind of way, you know? Okay.
Connell Barrett: Got it. Um, let me give you another really short list, and then we'll get into some practical tips here. But I want to give you one other little list here. Okay. I call these the four escalators because, on a date, there are four ways to escalate the date to the place where hopefully you both want it to go. Here are the four escalators and this is all in the book. Some of this will be familiar to you, but let's do a quick review. The first escalator is going from less personal to more personal. In other words. Hey, nice to meet you, Jennifer. Lovely weather we're having today. That's the beginning of the escalator all the way up. Wow. Now, you know my deepest hopes and dreams, and fears and I know you're getting very personal. First, the escalator is less personal to more personal. Personal. The second escalator is going from and this is a conversation I'm talking about. The second escalator is a romantic sexual conversation from less to the more romantic sexual conversation. So in other words, going from oh, hi you look really nice tonight which is a one in ten would be something much more edgy. Um, damn. I want to take you home and kiss every inch of you in the dark. Not saying again. Not saying. You need to say that. I'm just saying that would be closer to a ten, right? Mm-hmm. Yeah. Uh, or talking about romance and sex in a more. In more. Clear in a bold way. The third escalator is physical expressiveness going from not touching at all to what would be a one to a ten, of course, would be sex and intimacy. But then on the way, there would be things like high five hand holding, touching each other's arms, obviously kissing, brushing the hair out of her eyes, her doing some of these things with you back because it is a two-way street. So that's the third escalator. Physical, physical expressiveness. And the fourth escalator is logistical. That's going from one place to another place and eventually back to someplace where you guys can be alone. Her place or your place. So logistical is 1 to 10. One is you're sitting at the bar for 4 hours and you don't go anywhere. Ten would be you go from the bar to another part of the bar to a second spot. You go for a walk and then you end up back eventually or eventually either on the first date or a later date back at your place, and you can be alone. So you're logistically escalating things. So those are the four escalators. Um. In terms of those four. Which ones do you feel like you're not escalating very much, if at all?
Chris: I would definitely say physical. Like, I think logistically as I feel like that, you know, maybe I could do a little bit of a job with that. But I think that's generally pretty good cause you're the first or the first to continue.
Connell Barrett: The first one is personal. Less personal the more personal. Just being really vulnerable and getting to know each other and just opening up. And just seeing her heart and her seeing yours. Talking like talking about vulnerable things and real and digging deeper and kind of understanding who she is more at her core and sharing you. Right. So, for example, on a first date, I might talk about my failed marriage and how my wife dumped me nine weeks after we got married, and how scared and rejected I felt. And, I might open up that way. That would be a very personal thing to talk about or could be something positive and personal. Like my dad's 85th birthday, which is the best day of my life. And I talk about how my family, I helped my family plan this big surprise birthday party for my dad on Halloween, which is his birthday. So I'd be opening up about why that's the best day of my life. So that's personal, getting very personal, sort of on an emotional wavelength. And the second is romantic, sexual, basically flirting, being the man-to-woman talking and conveying things in a romantic or at least somewhat sexual way. And then the third is physical, expressive, and the fourth is logistical.
Chris: Yeah, yeah. I'd say it's kind of getting more personal. I'd said that stuff like something I feel good about. I feel that almost always happens on a date, okay? And typically has a good flow to it. I think it's more of that kind of romantic and kind of yeah, like that kind of talking about it is just kind of something that, I mean it happens and stuff on dates, but it's not very consistent. And what it does is it doesn't feel like this real connective thing, it almost just kind of is there, I guess. So kind of building that up in a more I guess can do Survivor kind of better flow too.
Connell Barrett: It or whatever. Yeah. And it sounds like physical expressiveness, there's a little bit of it, but maybe not very much.
Chris: Yeah, it's okay.
Connell Barrett: Got it. All right. So I think that this totally aligns with the seven essentials of how flirting, making her feel sexy is the one that you're not doing all that much. So going forward, do you have any dates lined up in the next week or two?
Chris: Not in the next week or two, but probably sometime after that. A pretty surprising job, at least a couple of dates.
Connell Barrett: Okay. Well, again, that inflatable woman is on the way so I can practice on her. Okay. I'm going to give you some marching orders here. I want to give you three, three practices to put in place on your next date, because what I think is happening and this is now making total sense to me, women see you as a handsome, cool, articulate guy. Clearly, you're a great catch. So hell yeah, you're getting dates, and hell yeah, you're getting second and third dates because women want to have this feeling like it's working. But I think what's happening is they're just not feeling the tingles, the feminine romantic tingles that they want, in addition to the personal connection they're probably feeling with you, but they're just not feeling, uh, deeply enough romantically. So I'd love to see you dial those up a little bit a lot actually in the coming days and see if that starts to change the game around. So here's what I'm gonna suggest. Here's a phrase I want you to start using on all your first dates. When the time is right, don't force it. But here it is. This is part. Part memorized, part improvised quote. You know what's really sexy about you? Dot, dot, dot. Then pause. See what she says. See, I should say how she sees how she responds. And then tell her. I don't know what that thing's going to be, but you'll find you'll think of something. Either you already have something because you've noticed her wit or her energy or her silliness or some funny little habit. Don't make it about her looks. Make it about a trait. Right. You know what's really sexy about you? What? What's really sexy about me? Chris, you make amazing eye contact. You just. I feel like you're looking through my soul and my soul is liking it or something like that. I just made that up, but something like that. Okay, uh, if you really want to be brave here, my man, you can. You can say. You know what's really sexy about you without yet knowing how you're going to finish it?
Connell Barrett: Your brain will find something. I promise. The cell field. But if you. If you want to know what is going on, just decide. What is it? What is it about her? That's sexy? That's cool. That just makes you kind of feel. Hmm. Okay, so, yeah. In other words, let her know something that is sexy about her, but make it a trait, a quality. Most guys say this if they say it at all, they say it about a woman's looks. And that's superficial. It's not a bad thing. It's just most guys have that feeling by telling her, you see the sexy traits she has inside. You're basically saying, I see. I see the real you. And that makes a woman feel like, wow, and that strengthens connection. But it's more of a romantic connection. All right. That's one thing to do. Second, I would love to have you going on your first dates where you're able to sit next to her. Or if you're doing an activity date, something where you're at least in proximity to each other as opposed to like across a table. Because on first dates, I want you to be a little bit more physically expressive. Think of it as stair steps. You start off with a nice hug when she walks in. Hey, nice meeting you. You look just like your photos. Hug friendly. Almost like a big brother. Like no sexuality? No, not necessarily sexual sexuality to it. Just a big, warm hug. And then you sit down, you're chatting next to her, maybe at the bar or seats where you're able to sit next to each other. And then she says something you like and you agree you can give her a high five. Or she says something silly and dorky. Let's say that she. What's it? What's a band that you hate or a movie that you hate?
Chris: Oh, I don't know. Like Ed Sheeran or something for a band. Okay.
Connell Barrett: Perfect. So let's say on your next dates, you're talking about each other's favorite bands. And as a musician, that's something that would come up. And you say, Hey, what's your favorite band? And she's like, Oh, I love Ed Sheeran. And you're like, What? Oh, man, I was really liking you until you said that. And you push her away, like, playfully for fun. Not really. But you kind of, like, give her a playful push. I was once on a date where my date said she liked such and such a group, and we were both on stools. And I literally turned her stool 180 degrees away from me. And I said, I'm sorry, you're on a two-minute timeout. I can't I can't be on a date with a girl who likes such and such a band. That's a playful tease. But I, you know, I had to kind of, like, slightly touch her and move the stool so you could do it when she says something you don't like or something you like. Right. And you're just and the way to make this cool and normal and not creepy hands, you guy, is you simply have a reason for the touch. The high five is a reason. Oh, no, I love that band or I'll get away. I can't date. And Ed Sheeran fan or. And then as the date goes on, feel free to be a little bit more bold with the physical expressiveness while noticing if she's enjoying it and if she's touching you back a little bit. Because if she's touching you back a little bit, then you can throw your arm over her shoulder and say, Oh, hey, I got a secret to tell you. And you throw your arm over her shoulder and you whisper something in her ear. It doesn't matter what the thing is, but the reason you're leaning in and touching her as if you have a secret. And now she's up. She's taking you in more physically. So she's feeling you're more like her. I don't like the word alpha male because I think that's all B.S. But you're just a man who's confident and comfortable with his physical expressiveness. And that's a very masculine energy to give out. And that helps her feel feminine, attractive. And also, as the date goes on, you can escalate to things like maybe you go for the high five and you catch her high five. You catch her hand, in a sense, and you hold hands at that point. You don't have to. You could also just take her hand and hold her hand, but that would be another escalation. Any time you hold a girl's hand on a first date and she's holding it back and she likes it, you basically now have the green light to go for a first kiss. Okay. I'm not at that moment maybe. I mean, think of it as a series of yellow, red, or green lights, but that's essentially a green light saying. She's basically saying, okay, next, you can kiss me. So that's why we're climbing the stairs. Step of physical escalation and expressiveness. And by doing this, it makes it so much easier to do the third step up and then gives you. Which would be to go on a date. Sorry, go for a kiss on a first date. If you're feeling that it's going reasonably well and she's responding well. Most first dates should include a first kiss attempt. If you're feeling a reasonable vibe from her and if you're attracted to her, of course, you don't have to do it if you don't like her. If she's arms folded, barely talking to you, never, ever, ever force it. Not that you would. You're a total gentleman. I know that. But I feel like a first date if we're relatively into each other. I want you to go for that first kiss because. You really can't lose if you go for it. If you go for it and she kisses you back. Guess what? Sparks are flying and she's starting to feel that flirty, innocent sexiness. If you go for that first kiss and she's not feeling it, she turns her cheek. Guess what? You still get points for trying. And you can laugh it off. Don't make a big deal of it. To my knowledge, Chris, I've never lost a girl by going for a kiss and gotten the cheek. I've gotten lots of them. Oh, hehe. Not yet. It's too soon. Or oh, I don't like PDAs. But they still basically liked it that I tried. I know for a fact I've lost girls because I had a window to kiss her and I didn't take it. And she is friends with me. They told me no because they told me. So, yeah, those are the three practical tips I wanted to offer you. Tell her something that she's so sexy about her. Uh, amp up that physical expressiveness by climbing those stairsteps and go for that first kiss at some point on the date. Assuming there's room, even if it's just a quick little peck on the lips, that it doesn't have to be a big old sexy makeout, although it can be. And if you do those three things, those three things, give it some reps, give it some time. You're going to get more comfortable and you're going to start feeling women. You're going to start feeling women, feeling your sort of Amanda woman interest in them. And I think they're going to get a lot more invested in you and want to keep seeing you beyond those two or three dates.
Connell Barrett: Any questions about any of this before we wrap up?
Chris: No. Yeah, that all sounds great. I mean, yeah, it makes total sense. Like, I totally see kind of, I guess the past, that kind of hold up and kind of what to do. So, yeah, like citizens.
Connell Barrett: Yeah. And a lot of this in terms of the romantic escalation thing, this part of this takes sometimes it just takes courage. Uh, sometimes you might just be a little bit nervous on a date and you're thinking, Oh, my God, she's so beautiful and cool. Oh, gosh, I want to tell her, or I want to show her. But what if she doesn't like it? Remember that. And I think there's a line in my book. Risky is safe. And safety is risky. Mm-hmm. If you do things that feel risky, that's actually the safe, smart move because we get to take risks in life, to get results and to have things happen. If you play it safe, that's a very big deal. Never escalating or not putting that flirtatious side of you out there, then that's actually very risky because you're risking the chance that you're just never going to make a woman feel the way we want them to feel. So I think it's a paradox. Risky is safe. Safety is risky. And I feel like, through no fault of your own, I feel like in some ways you've been a little bit safe on the dates, having safe, nice conversations, but not really, uh, not really putting that real man-to-woman self out there. So I say be a little bit risky and your comfort zone will soon stretch and expand and you'll start to feel more comfortable and confident while you do it. And then it just gets better and better. Makes sense.
Chris: Yeah, totally makes total sense. Yeah.
Connell Barrett: All right, brother. Great job. No, you have everything you need. It's just about tweaking these dials and realizing that, hey, this is a date. She's into you, you're into her. She wants you to flirt with her. She wants you to, quote-unquote, be a man, of course, a gentleman with empathy, which you are, but also be a man. We can still do that and go out there, give it a try, and hit me back with any thoughts and comments. And we'll stay in touch and we'll get you where you want to be. Sound. Yeah, sounds.
Chris: Great. Yeah, sounds great.
Connell Barrett: All right, Chris, thank you so much, man. And we'll talk again soon.
Chris: Yeah, sounds good. Talk soon.
Connell Barrett: All right. See you, partner.
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Welcome to the Dating Transformation podcast. I'm coach Connell Barrett, and I help men build confidence + connect with women by being their own authentic selves.
NYC Dating Coach Connell Barrett
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