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Episode #3

How To Talk To Women

Featuring Author Tripp Kramer
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Learn how to talk to women in this dating podcast featuring Tripp Kramer

Do you want to learn how to talk to a beautiful woman, but you struggle with what to say? Are you not sure what to write when you’re sending a dating app opener, or texting a girl? Do you run out of things to say on dates?

Not knowing how to talk to a beautiful woman leads to awkward silences, bad dates, and major frustration.

In today’s episode of the Dating Transformation podcast, Connell talks to a man who can help you always know how to talk to women, so that your dates, texting, and conversations become fun and flirty.

Tripp Kramer—author of the how-to dating book “Magnetic”—is a master at the art of how to talk to women. His insanely practical “How to Talk to Girls” podcast is one of the most popular pods in the dating industry. And has a LOT of wisdom to share today.

In this episode, Tripp Kramer will help you to…

  • Avoid “interview mode” and have engaging conversations with women
  • Stop sending texts that go nowhere, and start texting your way to more dates -Use his top 3 “game-changing tips” on how to talk to a girl to impress her
  • PLUS: Tripp and Connell talk about how to be flirty WITHOUT being creepy

Listen now so you can stop running out of things to say and start getting girls giggling, flirting, and meeting you for (great) dates.

How to Talk to Girls Podcast




"This crazy emotional rollercoaster we experience happens when we’re going through growth or going through something that challenges us."

- Tripp Krazmer

"As long as they do the homework and they stay consistent, it still shocks me sometimes, even though I'm the one who has the program for them."

- Tripp Kramer

"Being able to be successful with women will also give us good results and accomplishments in other areas too such as career and personal development."

- Tripp Kramer

"Shyness is temporary and it will not always be part of our personality."

- Tripp Kramer

Featured in the episode:

Tripp Kramer
CEO at Tripp Advice
Podcast: How to talk to Girls by Tripp Kramer
Book: "Magnetic: Cultivate Confidence, Become Rejection-Proof and Naturally Attract The Women You Desire"

Connell Barrett
Founder and Executive Coach of Dating Transformation

Connell Barrett is a NYC dating coach who's helped thousands of men all over the world find their soulmates while dating with integrity and authenticity. His Dating Transformation podcast gives valuable tools and tips from industry experts on how to get a girlfriend. You can find Connell’s book, Dating Sucks But You Don’t, in bookstores nationwide.


00:00 Introduction
01:54 Tripp’s dating problems in the past
06:03 Connell approaches a woman for the first time
06:56 Tripp’s breakthrough moment
14:26 Tripp steals Tom Green's girl
18:37 Learning from mistakes in dating
24:39 How to take action
30:23 Success stories
34:58 How getting good with women is a gateway drug to success
39:21 How to talk to girls
42:35 Dos and don'ts of texting women
45:34 Game-changing tip to get better dates
49:14 Advice for the dateless
50:33 How to contact Tripp

Produced by Heartcast Media.

Related Episodes:

How To Start A Conversation On A Dating App

How To Flirt With Girls


Connell: And we are back. And I'm really psyched to talk to today's guest. Today, I'm talking to an absolute shining light in the dating industry. Tripp Kramer is an international dating coach for men. He created his TEDx system, which helps shy men confidently attract the women they desire. In his earlier years, he was a shy guy himself who figured out through trial and error how to get better at meeting, dating, flirting, and finding the right type of women for him back then, and now he helps guys like you find the right type of woman for you. He currently has a popular podcast on iTunes called How to Talk to Girls. I know it's really good because I was on it and I listened to it. He's also got a really good book called Magnetic, which teaches all of us secrets on dating and attraction. And Tripp also has a very results-oriented training curriculum called the Trip Advice Accelerator Coaching Program to learn more good at That's Tripp with two P's advice dot com. Tripp, Thank you so much for being here during launch week. I'm psyched to have you.

Tripp: Connell Man, this is great. Thanks for having me. I love when I have guests on my podcast and then I hear that they start a podcast and I get to be a guest on theirs and we just get to do it all over again. So thanks for having me, man.

Connell: Well, this is week one for me and you've been podcasting since the B.S., I think a little few years before Christ. So that's right. I'm humbled to be in your podcasting presence. Speaking of who you used to be, let's start with that shy guy who you used to be because the guy listening to this is probably on the shy, introverted side and he's got some dating problems. Totally. What problems did you have back in the day with women and dating?

Tripp: So it was a lot. Oh, we'll start there. First of all, I was a shy person. I considered myself a shy person around new people. Okay. So I wasn't super shy, maybe a little bit, but not super shy around friends or around people I was introduced to. You know, at that point it would be a little bit easier for me. But if I wanted to meet anybody new, especially a woman I was attracted to, I would be very shy. And this was my whole life. And on top of that, I call myself the friendzone a nice guy because that was me all the way up until my early to mid-twenties when I started to learn how to get out of that mindset and stop getting friendzoned and really understood and learned what women were attracted to and what they wanted. So I was, you know, I would consider myself lucky if I ever got a date and the few and far between times that I did in my college or early twenties years. And I, I basically had a breaking point where I said, I can't live like this anymore. I don't want to leave so much up to chance. Hmm. Okay. Which means I just don't want to, you know, settle for a woman that I may end up matching on a dating app. Although at that point, there was no real matching. You just kind of like it. Message people. I was doing online dating apps back in 2008 - 2009. Right.

Connell: Pretending basically. Right. Yeah.

Tripp: Pretender. And then I wasn't meeting any women outside of that ever at all. So I was fed up and I went through on my own. Long story short, my own journey where I had to learn how to go through the process of meeting women. And because I wasn't getting any results online and there weren't any gurus out there who were teaching online dating and how to get good at it. There was pretty much nobody because it wasn't hot at that point. I had to go out and meet women. I had to go out and approach women, whether it be during the day or at a bar or wherever I could, or maybe I was invited to a party and had to do it there. And so I put myself through a long one, two, two-year regimen of consistently socializing and approaching and putting myself out there. And it was every emotion you could ever think of. It was scary. It was fun, it was shitty, it was awesome. It was at all because any time you're going through growth or you're going through something that challenges you, that's what happens. It's this crazy, emotional rollercoaster. And through that process, again, long story short, I was able to figure out how for myself to be able to break out of the shyness, and how to be able to attract the women that I wanted. And then it got to a point where I was so obsessed with my journey and my progress that I was like, If I could do this, other guys could do this. And I knew that other guys were learning this stuff. There were other dating coaches at that time, so it wasn't anything novel to think about. Like, I should teach this. Like, no one's doing that. Plenty of people were doing it, but I thought I had a method that was a little bit different from other people's teaching. The kind of just like an average guy who wasn't looking to be some pickup artist because that's what was hot in 2005 to 2010. Oh, yeah. Just how to like me women and do it in a really non-sleazy, non-manipulative way. So that was my journey from figuring it out myself to then starting TripAdvisor where I wanted to help other guys do it.

Connell: You mentioned the fear and the scary part of this, especially when you start. And I remember I literally remember the first woman ever approached. I remember the first night it was July 9, 2009. I was going out on the town in New York City, and I had so much fear and anxiety inside that I actually went into the men's bathroom before I ever talked to a girl. And I basically had a panic attack and I got the dry heaves. I didn't know what it was. I now realize it was just this fear of the unknown and the fear of basically finding out I'm not good enough. And then I. I approached a really cute girl with a white cowboy hat on. It went fine. She wasn't into me, but neither did she, like, blow me off and laugh and just, you know, tell me to go f myself. She just was like, Hey, nice meeting you. And I remember thinking, that's not so bad. I can take that. Do you have a memory from back when you were just learning this and you were out coaching yourself? When did you feel afraid? What were some scary moments? And maybe what was a breakthrough you had?

Tripp: Yeah. I mean, I have so many stories, I know where to begin, but I have so many different types. But I'll say the one that I think might resonate with the audience the most, was I. So I wanted to learn how to be just like you. Right? So I was just maybe doing it only like six months or like one year before you were doing it. I was doing this in around 2008 and I. I'm trying to think, actually. You know what? Let's. Yeah, okay. I started even earlier. So what happened was I knew I wanted to learn this, but I wasn't confident enough to do it by myself or go out alone. So I remember that there was this group of guys on the Internet and this forum that I found who were getting together and learning how to do this later.

Connell: Was it a.

Tripp: Layer? It was a layer. Yeah, that's right. And it's funny because, you know, when you talk about it in the way I go, it was like a pick-up layer. It sounds a lot creepier than it really is. And I thought it was creepy, too, until I met these guys and they were just great guys. Yeah, they were really good guys, really nice dudes, all just like me, you know? It was just guys trying to figure out, like, personal development, and then how do you meet women? So become friends with some of them. And I think I texted a guy or called a guy and I was like, Wow, I wasn't even that close to it. I just met him one night. I was like, Hey, man, I really want to go out tonight. I know that you're better than me. Can you just, like, push me? And as I was saying that, I was really scared because I was like, I can't believe I'm doing this. Like, I really had to push myself to do it. But I knew if I just had someone else kind of do it and help me, then I was forced to go out and I had no choice. So he's like, Yeah, man, for sure. Like, it's not a problem. And he was like, a really social guy. And he was like, really? He has already gone through his process. So we go out to this bar and I was trying to learn this sober. So I didn't want to learn this with, you know, drinking and getting drunk because that wasn't even helping before. So I was like, all right, let's, let's do this. So he goes out and this guy is like life. The party's choosing everyone. And with his water that he got. And I was just like, okay, I was like, I don't know how to do this. And he's like, all right, just like, go, go talk to like, that group over there. And there's like, I don't know, two girls and a guy or something like that. And he said, Use this opener. I don't even remember what it was. And I went over there and I use the opener and I said, whatever. And they all looked at me like I was crazy. I was like, Oh my God. I was like, really? Like the first approach that I finally did. And they all just, you know, they looked at me like a deer in headlights, like I said something. And I remember I liked what I said. I know it wasn't some weird pick-a-B crazy line. It was something very generic, which is probably why I don't remember it. And I got the worst response. So I was like, All right. And then that's my only memory. From that night, maybe I approached a few others and it didn't really work out. And I was like, Oh God, this is terrible. So I said, Okay, you know what? Maybe I need to take this a little bit slower. Instead, I'm just going to go out alone and go at my own pace and maybe not go to some heavily trafficked, you know, very popular place. So then I decided to hit the streets of Hollywood at around 9 p.m., all alone. And I was out for 3 hours, and didn't talk to a single soul. And I was like, Oh, my God. I remember this so clearly because I had a little journal where I wrote down the kind of like my progress, like how I was doing. This was like night one, 3 hours.

Connell: Nothing, not probably 15 times. You want to do an approach and something probably stopped you.

Tripp: Oh, at least that, right. At least that. And what stopped me was, you know, everything, the fear, and fear of rejection and also having I didn't have a game plan, I didn't know what I was doing. I just was putting myself out there. So. Then I think it was maybe the next week or a couple of days later I went out again. And it was for like another 3 hours. But finally, at the end of the third hour, I said hi to one girl. It was literally like she walked by me and I was like, Hi. And then I kept walking and I had this moment. I was like, This is just so bad. This is going terribly. I was like, What am I going to do here? I mean, I was like, this is just not for me, I guess. Like, this is just now. It's just not meant to be for me. I don't know. It's not going anywhere. And I thought, well, I could give up. And then what happens if I give this all the thoughts racing through my head? Okay, if I give up, I'll end up in the same place. So like nothing's going to happen. But if I keep going, well, at least there's still some hope somewhere, maybe. So logically, I was like, I guess I'll just keep going. I don't have anything to lose at this point. And so that motivated me a little bit. And then I went out the next night and I said hi again to a girl, but a little bit faster this time. It didn't take me 3 hours because I did it the night before. Right. And so now I'm like, all right. And then I went out. Then I think it was like a couple of hours later, I said hi to another girl. Maybe talk for 2 seconds. And it's like, you know what? Okay, I did better than yesterday. Probably nothing crazy, but yeah, it was progress.

Connell: Forward motion.

Tripp: Forward motion. I said, all right. This is something, it was just this small little baby fire that was just starting to get going. I was like, all right, let's keep going. So over the course of the next 3 to 4 months, every time I went out, I did a little bit more, a little bit more until I got to the point where I was having full conversations with women. And then until the point where I was starting to then feel more comfortable having conversations with women that I could focus a little bit more on flirting with them, and then I could focus a little bit more on maybe talking to groups of people. You know, there are multiple women and there's guys involved and all that and then grabbing the attention of the group. So it's just this slow process, but it only took maybe about 3 to 4 months until I started getting a lot better at it, but only because I was putting so much effort into it. I wasn't going out once a week for three or four months. I was going out and sometimes up to seven days a week. I was going out every single night. I was going out just to practice talking to women and sometimes on Saturdays and Sundays during the day. So I really, really pushed it. And that's how I got through my initial approach, anxiety and talking to women and learning how to do it.

Connell: If you can think back to that next, that 3 to 4 month period after you said, okay, I'm going to keep doing this, what? And what aha moment did you have or interaction that all of a sudden you took things to the next level? Do you remember any breakthrough moments during those three or four months?

Tripp: Yeah, totally. There was one moment when it was this bar that was in the valley and the people were there or a little bit older. So it wasn't like a super young crowd, even though at that point I was young, I was 23, 24 years old, and was a little bit older, but also very attractive people. And also don't remember who Tom Green is.

Connell: Oh, yeah. Yeah. He used to be Drew Barrymore's husband, and talk show host.

Tripp: Yes. Yeah. Silly guy. So, anyway, funny, he was there that night and I was trying to why? I didn't know it was his girl, but I was like hitting on his girl and he, like, comes over and gives me a dirty look, and he, like, pulls his girl away. And I'll never forget that. If you were around during this time going out, you would know who Tom Green is, and you would think that's a big deal. But anyways, now he's not really very relevant. Anyway, so later that night. I went up and approached a group of people, like a large group, like six people, men, and women. Again, a little fuzzy. This is over 15 years ago when I read much. And so I don't remember exactly what I said, but I know I went in and I said something and I just went in with a lot of, like, fun, energy and just, like, super positive. Right. And they responded really well to me and that was really nice to have because they kind of showed me off the bat, Oh, you know what? Maybe this whole group interaction thing isn't so bad. And it got to the point where I was like talking to the guys, making friends with them, flirting with the girls, and ended up getting a number from one of the girls, and it just blew my mind. And I look back, I go, I couldn't even say hello to a girl walking down the street. And now I got a number off of a girl who was in a group of guys and girls, all because I was just having a good time. And that was my mindset too. I wasn't really going in there to say like, Oh, that girl is cute. I'm going to get her number. I was just like, it was one of those nights, and many of those nights were like this where I was like, I'm just going to go and have a good time, socialize, have fun, be independent, and just enjoy this process as much as I can. And lo and behold, what happens when you do that? Well, at least for me, that night, I was able to get some numbers and just have an enjoyable experience socializing and meeting people. And I'll just never forget that night because that night really taught me, I guess, to kind of sum it up and tell me this is so much less of a big deal than I've been putting, than I've been making it out to be. You know what I mean by that?

Connell: Oh, yeah. Well, yeah. I mean, that first night when I was in the bathroom, dry heaving, not realizing it was a panic attack. Yeah, talk about making it a big deal. I was making it. It was all about my value and worth was on the line. And if a guy goes out to, quote, approach women and create attraction and puts his focus on the outcome, to your point, if he's dependent on that outcome and tells himself a story that I need women to make me feel attractive and worthwhile as a man, you're raising the stakes to such a place where it's going to be hard to relax and just enjoy it and be authentic and have fun. Do you agree?

Tripp: Yeah. 100%. 100%. And that's what the girl is who she's attracted to. She's attracted to the guy who's just enjoying himself and having a good time. And that energy and that energy is just really, really attractive. So now, listen, it might be really hard for a beginner to access that energy when they start to go out because it's not a fun time. I mean, I did not have a fun time. It took me weeks until I was having a fun time. It was just working at that point and a process that I had to get through until I started to become a little less. Nervous. And then it started to become more fun. Now, that doesn't mean that that can't be for other people. Maybe for other people. They do start right away. And it is fun. Just for me, I was. I had so much anxiety about it. Yeah. Similar to you, Connell, it just took a while for me to enter fun mode.

Connell: Right? Totally. Okay, here's my time machine question. I was going to ask you this anyway, but this is the perfect way to ask it. If you could go back in time and get in your DeLorean, your time-traveling DeLorean, and go back to that first night, that three-hour night when you couldn't talk to anybody if you could talk to younger Tripp and give him one word of advice or encouragement, what would you tell your younger self?

Tripp: I mean, I would probably tell. Well, first I'd like to be like, dude, I know this is going to sound crazy, but one day you're going to be teaching this stuff. But I know that's not what you're asking, so. Okay. But what I would say to that guy, I would say to him. Well, I mean, it's kind of at that moment. I didn't really know if I was right or going about it the right way. So it's almost like a reassurance that I would tell him, Hey, you know what you're doing in the process, that you're about to begin here by taking it step by step? Yeah, you're right. You're onto something here. And this is correct. And just understand that. And, you know, I'd probably tell you the Tony Robbins quote, which I might butcher, but I think it's people. Overestimate what they can do in a month. And underestimate or know. People overestimate what they can do in a year. And underestimate what they can do in ten years. Right. Okay. So that means that a lot of people kind of want a lot of fast results and they want a lot. So they think like, okay, I need to get all this and achieve all this, you know, in the next year or the next whatever, you know, next week, the next month. But then they don't think about the longer term and realize that the consistency you can achieve a whole lot. So in this case, it'd be nice to hear from my future self that the process that I'm about to go through, it's going to take a little bit of time, but if you just keep going with it, you're going to achieve results.

Connell: Right. If I went back and talked to my younger self, my younger self would look at me and go, Oh, my God, you're so fucking old. Whoa. And I would say, Drink less whiskey. The other thing I would say to my younger self would be if I could talk to that guy who is hyperventilating in the bathroom, I would say, Bro. Women like you. It's okay. There's nothing at stake here. It's okay to have butterflies. But don't think that any approach or any night out meeting women is going to be some verdict on your worth. You're enough. You have so much to offer, so have some fun tonight. And hey, that's what I wish I would have known.

Tripp: That's good. I like that. Yeah, it's. It's. It's a shame we don't have our future selves to come back to, but I think maybe it's about putting a little bit of. I don't really love the word here, but hope, I guess, into the future. But hope means you know. Yeah. Field of Dreams. If you book it, they will come. Right? So if you put the right steps into place and you stay consistent with it, you will get there. I know that much. I mean, the guys that I work with and who we coach over here at TripAdvisor, I mean, even sometimes I think like, huh, this is a real hard case. I'm curious to see what happens. And as long as they do the homework and they stay consistent, it even still shocks me sometimes, even though, like, I'm the one who has the program for them, right? They do. Like, I'm working with one guy right now, and he's got a lot of things against him in terms of what would make him attractive. He's very short. He's like five-two. He's not from America originally. So that means that he has an accent. Right. And obviously, it's going to be a little bit harder for you with an accent here in America versus if you're just from here. So he's got that against him. He's over 40. He's divorced and has kids. So, you know, we're starting off pretty rough here. And lo and behold, within just a few months, he was able to sleep with women he never thought he could sleep with. And then just a few months after that, he is close to having a girlfriend, you know, multiple dates, all that stuff. And so a lot of guys really put so much emphasis on their looks. And I'm introverted or I'm this and I'll have money and this and that, whatever it may be. But you would be shocked. What can happen if you literally just put yourself out there? So this is maybe another thing I'll say to your audience, too, and maybe what I would have said to myself, my past self is if you just never listen to a podcast again. I say this a lot. If you decide to never listen to a podcast ever again, you never get a drop of dating advice on the internet or from a friend. And you could just do one thing. That would actually get you a lot of results. So meaning you don't have to read a book, read a tweet, or watch a video. So let's imagine you do nothing of the sort, but you just dedicated three nights or days a week and just said, I'm going to go talk to people. I guarantee you. In three months, you'll have gotten plenty of numbers, at least some of the few girls. You might even get a girlfriend. I think most guys just don't put themselves out there and they don't allow themselves to get enough volume. They stick within their shell because they're nervous. Of course, I understand that. Maybe they just stick to their social circle where there's not a lot of volume there. And so. Sometimes it's just a numbers game. Now, of course, I wouldn't say, you know, I wouldn't actually tell any guy to do that. They should listen to podcasts like this. They should get advice. They should do that because that's going to make the process go faster and get better results. But if you couldn't and you just talk to enough people, a lot of very interesting things would happen.

Connell: Yeah. Well, it comes down to this information. No matter how good it is, I think information is overrated and execution is underrated. In other words, take action to your point. In fact, it's still funny that you brought this up because I wanted to quote something you said on a recent episode of your podcast, How to Talk to Girls, because you said this and they had me just nodding my head. You said in the podcast that when you first began working on your dating life, you said, and I quote, I read tons of ebooks and tons of information. But the real learning came when I just said, fuck it, I just went out. I was sick of reading and sick of watching, and I finally needed to put this stuff into practice. I threw away my ego and took action, end quote. And I just love when he said that, because basically you just said what you said a minute ago, which is, hey, information is great, but you got to go out there and dive in and start swimming to see those results.

Tripp: Yeah. And you just I like to say this on my podcast before you'll, you'll learn things by going out that you won't learn from anybody else though that, that myself, Connell, you and the other, you know, coach in this space won't be able to teach you because there's this experience that you're having when you're interacting with women that's making all these little connections and the neurons in your brain that's helping you progress forward, that's giving you the references that you need, that you can't just hear or watch, but actually experience that gets the learning process to happen that much faster. Here's a great example. Let's imagine I was learning how to do a squat. If anyone can learn how to squat before. There are a lot of little things that you need to do to make that form go well. I can watch videos, I can hear about it, but I'm not going to understand it really unless I'm getting under a barbell and doing the squat. And then I can understand more about what does it feels like. Okay, this is what it feels like when my legs are this far apart or this. This is what it feels like when my neck is up versus down. All those little things that are going to help you progress further right can be the same thing as anything else. I can give you another example like a guitar. I can watch them and play the guitar all day long, but I'm not going to really understand how it works and how to learn from it or learn from the information. If I don't understand what those strings feel like under my fingers.

Connell: Totally. Yeah. There's a line in my book, a Bruce Lee quote If you want to learn to swim, jump into the water on dry land. No frame of mind is ever going to help you. It's not going to get you in the water no matter how much you think about it. Yeah. And I also tell it, there's an anecdote in my book where I talk about how I used to become a bit of a seminar junkie, in other words, an information junkie instead of an action junkie, which I should have been. Yeah, but I remember. But I was taking action. I was seeing some nice results. And I remember I think I think it's easy for men to use all this information out there. Amazing podcasts like yours and good books like both of ours. And hey, I'm pro positive information, don't get me wrong, but it can turn into a form of creative avoidance for doing uncomfortable action, at least uncomfortable at first. And I was at these seminars, was a guy named Jerry Gerald at all these seminars, and he had tons and tons of notebooks stacked really high listening, writing all these pick up approaching dating, flirting secrets, and tips. Yeah, I broke the ice. I finally talked to him one day. I said, Hey, Jerry, how's it going? How's your journey going? Assuming he was going to tell me about dates or approaches at the very least. And he said, Oh, I haven't talked to any women yet. I'm still learning the theory. And I have heard that so many times. Yeah. They won't be a seminar junkie. Don't be an information junkie. Throw away your ego and say, all right, let's go take some action. And then you're going to learn so much more from taking action than it's going to be uncomfortable, but it's going to be so much more.

Tripp: I mean, I said that, too, by the way. I don't know if you ever said that too. I was like, Oh, I'm just learning. I'm just yeah, I need to learn the theory first. I absolutely was saying that. And in fact, so I mean, I cringe when I say it, but I have to so everyone can learn and maybe laugh. Like I was studying this stuff. I mean, I downloaded e-books on e-books. I had little note cards. Like flashcards, if anyone even remembers what flashcards were. You did that with, like, math. You'd have a note card with like five plus five. And then you look at it and like try to know what it would and the sum was, and then you turn it around to have the answer. I had that for, like, meeting women. Like, different lines, different things to say. Hmm. And I went through it. And by the way, none of it really helped me. Like, it didn't do anything. And I was just trying to memorize all this stuff before I went out there. But finally, I was like, This is stupid. Lewis threw away all the flash cards. I threw away the books that I printed out. And that's when I decided to just go out. And I was like, I just got to go out. I got to just see what happens because this is not getting me anywhere, and I can't memorize all this shit. It was too hard. Yeah.

Connell: Back to your coaching. Or I should say when you got into coaching, do you have a favorite client success story or maybe just a guy you helped back in the day, maybe even before you became a professional dating coach and expert? Was there a success story that just let you up so much? You said, Oh, my God, I got to do this all the time. This feels great to help men.

Tripp: Yeah. So I'll tell you that. Okay. So it was 2011. I first started with Tripp's advice. I had no idea how to market a business. So all I knew at that point was, was podcasting because I had a podcast, not the one I have now. It was another podcast where I gave dating advice. Hmm. And so I was. I was utilizing that to try and get clients, but. I didn't really know for sure if I could do this yet. So before I even advertised on the podcast that I was offering coaching, I had to test it out. So I wrote an ad on Craigslist and I said, Free coaching, you know, something along the lines of, I'm a dating coach for men, I'm offering this for free. And the first person who responds, I will take you out and I'll help you, approach women. So funny enough, I only got one response. Okay, and that's fine. I got one response. Okay. This guy was tall, he was handsome. He was actually somewhat charismatic. And he was like a popular dj in the underground scene. So it wasn't super popular. The average person wouldn't know him, but apparently, he had a pretty decent following from what I remember. And I was like, Wow, this is so funny because here I am about to coach my first client. And who do you expect to see? A nerd, a short dude. A guy who's an engineer. But now I got this, like, deejay, and so who's like, a decent looking guy. And I'm like, listen, man, I got to ask you. You need help. You know, and that was I think that was not really super cool of me to kind of state it like that or even be kind of ignorant to the fact that maybe other people needed help. And it's not just like the cliche person who you would think would need help. But I didn't know. And I was like, he's like, Yeah, man, I'm super shy around women. He goes, When I deejay, I get all these cute girls around me and they're all loving what I'm doing, but I am freaked out. I can't talk to any of them. I said, Wow, okay. So that's my first lesson to know that it doesn't matter what your status is, what you look like, how much money you have, or any of that, you could still be a super shy guy, right? So I said, okay, let's do this. I'm going to take you out. So I took him out to a bar in L.A. I helped him approach women, and I did it in the way that I thought, you know, okay, this is probably the way I would want it to be done. Just starting off kind of slow, like, okay, go over those two girls. Say this line, you know, something really easy. And then over the course of the night, it went from him sweating bullets to going over to these women to at the end of the night, he was socializing with everyone and having a great time. Yeah. Now, it wasn't a crazy story, like I can say, like. And he got laid or he got a girlfriend or he got a, you know, that stuff didn't happen. But he stole.

Connell: Tom Green's girlfriend.

Tripp: He's exactly the one who started Tom Green's girlfriend. When that happened, though, was at the end of the night, and he was so thankful. He's like, this was one of the best nights of my life. This is amazing. Thank you so much. I like this way, this is great. I cannot thank you enough. I feel so much different than I did before. And I was like, wow, that's great. So that was enough to give me the fire to be like, That's it. I'm doing this like, you know, like one and done. I don't need to coach anyone else for free. I can do this. So that was my very first client, so to speak, that really showed me that I can help guys.

Connell: It's addictive. Nothing feels better to me when I get that text message or see a guy, Oh, it's just because I remember how that felt. I was so introverted, so shy, so in my head about being this nerdy ginger who women wouldn't like the authentic me. And then once I flipped that with my coach's help, it just was life-changing in ways, way beyond dating. Yeah. Which is actually what I wanted to ask you next. I found a quote of yours. I forget if this is from your book or maybe it's something you wrote, but I saw this online attributed to you. The quote is Getting good with women is a gateway drug to success. Could you elaborate on that idea inside of dating or outside of dating?

Tripp: Yeah, I think that was from my book potentially. What I found was. I found a pattern that happened with myself and it happened with a lot of guys that I was friends with in this community of guys learning how to get better with women. And then I found it through the guys and I started a coach and I found this theme where all these guys would learn how to meet women. And once they got good at it, it didn't stop there. They started focusing on all the aspects of their life. They started learning. A lot of these guys became who I'm talking about, maybe became entrepreneurs and started businesses and guys who went out or went on to do better at their work, or guys who started to get really into while, Hey, I can do that. Let's, let's lose weight, let's get jacked liquids. Let's work on my health and just get really into all these aspects of personal development. So again, that happened to me. That happened to a lot of people I know. And so that kind of explains the quote is like, you know, you get better at this and it's so hard for a guy. That once you accomplish that kind of thing you almost say to yourself, like, what else can I do? I did this thing that was so hard. What else can I do? And years later, I realized a couple of things. First of all, the reason why this happens, at least my theory on this, is because they've built their self-esteem. Right? So, someone who has low self-esteem, they're not going to really try to do hard things. They're not going to really push themselves because they already think that they suck. So nothing's going to really happen. It's going to be really tough to get out of that hole. So self-esteem is built by. Keeping the promises that you make to yourself, and can be in any form. And once you do that and you get results and you say, wow, I'm awesome, I just did something that self-esteem pushes you to be able to do other things. So that's one thing. Also, when it comes to men. One of the things that I feel like a lot of men relate their worth to is that before they may learn any personal development or go through any therapy or anything. A lot of guys relate their worth to how women view them. It's just part of our nature, right? It's like if we end up with a girl, we lose our virginity or a super. The bunch of girls, we feel amazing. We feel attractive if we get rejected by some girls or we have no sob stories from high school where it didn't work out. You got friendzoned, you don't feel as great. I mean, you can even find it funny, too, because I work with a lot of clients who say the same thing. Oh man, my job is great, my personal life is great. All this or that person, like my job, is great. My workouts are great. I feel like I got it all, but I'm missing that one piece of the puzzle and it's women and they feel very incomplete without that piece. So there's something about our relationship to being able to be successful with women. That I think is one of the hardest for a man. And so when he's able to get some results or accomplishment in that area, it just really picks him back up.

Connell: Right. Well, there's various ways to feel. Worthy, significant as a man. Right. You can climb a mountain and you can become a billionaire or a millionaire. You can build an empire, become really ripped, and have six-pack abs. Those are all valid. However, I would argue maybe the most powerful way or at least the most universal for the straight guy listening to this is becoming feeling your worth, your confidence, your attractiveness to women. Yeah. So if a guy's life, if your whole life is or you got the job, you got friends, you got cool hobbies, but there's just nothing happening in the dating front, then your whole life can kind of feel out of balance. It's like the analogy I use is like a bicycle tire with one broken spoke. The whole tire is out of alignment or a guitar with one string that's totally off the whole strum sounds off. So if you're dating, life is if you're hurting with women and dating, it's okay to realize that and work on fixing it because you're going to elevate. It's going to lift all the boats of your life once you get this handled. That's my view.

Tripp: Yeah. Yep. 100%. 

Connell: Okay. So your podcast called How to Talk to Girls, and that's probably one of the most universal problems that guys come looking for help with is like, what do you say? How do you talk to women? What words do you text? and how to communicate. It's so important. So I'm going to ask you for three game-changing dating tips. Everybody does this. I'm on my podcast so far. I do this with all my guests. And let's start with how to talk to girls. I mean, this is your area. What would you say is the first game-changing tip, a piece of practical advice you would like a guy to know to help him learn how to talk to girls?

Tripp: Okay. One of my favorite ones. I do talk about this quite a bit, especially on my YouTube channel, but it's really important to help get off that nice guy from is and it's going to take a while to practice this one because it's so it's just so part of who you are that it's going to be hard to get out of this. But it takes practice, which is. Try your best when you're talking to a girl when she's talking about herself, whether you're approaching her on a date or ever. Not to agree and nod your head. Yes. And and and verbally agree with her on everything she says. Hmm. Because the reality is.

Connell: That. I mean, let me shake my head and disagree. Hmm. No. Okay.

Tripp: Go get fast, learner.

Connell: Practice.

Tripp: Yes. The reason why is because women don't like men who are too agreeable. I don't think anybody actually likes anyone who is too agreeable because it's fake and it's not real and it looks weak. And women are not attracted to emotionally weak men. So. So. Be careful to not sit there then. I'm not even saying to fake disagree with her, but look for those moments in the conversation. You know, she's like, you know, I really like country music or something. And you don't let her know you like country music. Oh, that stuff's the worst. Got a real great tip within that tip if you're disagreeing or you're being playful or teasing. Smile. Because smiling just allows you to get away with more. And it's not going to come off so harsh. So don't be scared of that. Okay.

Connell: Right, exactly. Oh, you like country music? Really? Really. When did you break up with your cousin? Yeah. You can have a lot of fun with that.

Tripp: That's great. That is.

Connell: That's so. My thing is all about authenticity, right? Be truthful, be your true self. And that's going to include saying things that might not agree with her. But it's also good advice to your point. Okay, cool. What's another tip to talk to girls? What do you got?

Tripp: Okay, let's go digital now. Okay, so texting. I actually said this to a client earlier and I was like, I got to talk about this in a podcast, so I'm going to quote myself. Nice. And it is right here. So my client asks me, curious if you think there's anything clever, flirtatious I can or should say as a follow-up to a call? Sorry. Out of context. It was a girl that he was not going to meet up for a while. So he's asking, what can I text that's flirty and clever and stuff? And I said the best flirting over text is no texting. So. And then I said, Makes her think about you more, and that drives her wild. So, guys, when it comes to texting and I'm really trying not to sound like an old man trip over here. I understand. Trust me, I'm. I understand that texting is so prevalent. I'm texting all the time as well. But I'm not talking about, you know, trying to be old school and not text. What I'm saying is there's so much more room for error. So if you're texting all the time and you're trying to be flirtatious over text. There's more downside than upside to that. Like, even if it hits and you see something flirty or funny, it's not really going to make that much big of a difference where she's going to go, Oh, now I like this guy because she already likes you. Or she does. But if you say something wrong. Then you have a lot of downsides because she's not going to like that text, whatever it may be. So stop trying to be flirty over text. Try to use texting more to meet up and less for trying to build attraction.

Connell: Yeah, you're always using you as I understand it. Like to use texting primarily for hey, let's move this towards meeting up because that's when we can make something good happen. Yeah, that's all right.

Tripp: Yeah, exactly. And some guys go, well, what if the what if I'm not seeing her for two weeks? Well, if you're not seeing her for two weeks, you should be dating other women on top of this that you hopefully are seeing a lot sooner and not just waiting around for her and at the very worst. I know this is going to sound contradictory to my advice, but I do believe it. Yes, if you're if you have a date that's set up like 10 to 14 days out, that attraction can die because she's kind of forgetting about you. It's been a long time. So if you have to do some sort of like ping. You can texture a picture of something that you're doing that's interesting or similar, interesting that you are, and you send the picture and that's it. And don't get into a long conversation after that. Just send her a picture of it and then move on. Right. Insert dirty joke here. But I think you guys know what to do with that picture. Okay.

Connell: Awesome. We have time for one more game-changing tip about how to talk to girls. It can be something completely off that topic. Whatever you got, whatever you want to throw at us.

Tripp: Okay, let me see if I can go a little bit more little wider with this tip, a little bit more macro. Okay. So I want to connect to what I said earlier about volume. Remember earlier I said, you got to do a lot of volumes and it was just a numbers game and you learn nothing that you end up getting some results. So based on that concept, what I like to teach and what I found works really well, especially in 2022, and I can't imagine this changing in the next 20, 30 years. You really do need to put in the volume. So you need to be swiping on your dating app. Up to an hour a day. And you need to be going out and talking to at least 15 women per week. Hmm. Okay. Now to some people who are going to say that sounds fucking crazy. That sounds like a lot. And here's the thing. If you're not doing that and you're getting the results you want, that's great. You don't have to do that. Right. But if you're sitting here and you're going, oh, I'm not doing that much, but I'm not getting the results I want. Well, then you should be taking that advice. Yeah. And then if you end up taking that advice and it starts to work, you don't have to keep up with that. If you're like, Oh, I'm slammed. I got a bunch of dates set up. Great. Then you can. You can pull back. You know, but. You have to put in a lot of effort even if you're a super good-looking dude, even if you're super charismatic and you learned all this stuff, like every guy, this, there's no exception here. Every guy needs to put in a lot of volume because there's so many women. Now, I can go on a whole rant, but there's the women now who are becoming more entitled. And because they have so many options, I actually don't even blame them. Imagine a guy. Imagine you as a guy. Hypothetically, you had women clawing at you, trying to get your number or swiping on your left or you had all these options. What's going to happen? You're going to become a little entitled. You're going to think that you deserve the best and you're going to be more picky. So now that technology has. You know, get to the point where it's shown even to an average woman that she has so many options. Mm-hmm. Most women now are being choosier than they ever have been. So what does that mean for you? I mean, so the average guy. He needs to put in a lot of volume to get results. So I don't want you to put some new photos up on an app swipe for a couple of minutes a day, approach a couple of women a week and not get results and go, Well, I did it. I tried. Nothing happened. Nothing happened because you need to put more effort in. And that's just the name of the game.

Connell: Yeah, that's a guy that goes to the gym, you do two crunches and then you have a smoothie and then you go home saying, Well, Lisa, I went to the gym today. It's like, no, you got to put in the action to get the results. Yeah. By the way, I'm really intrigued by this idea of an old man trip. Like, like I envision a 97-year-old man dating coach who's like, oh, back in my day, we, we, we sent dick pics using the telegraph. There's a sketch character in here. I want to write this sketch character so that we have just a minute or two left here. Two final things. Any parting shots? Is there anything I didn't ask you? And you want to talk to that shy, possibly dateless guy out there? He's listening to these parting words of wisdom. What do you got?

Tripp: Yeah, man. I mean, just know that shyness is not. Hey, it's not. Permanent. You know, like don't look at shyness or like or like introversion extroversion, all that stuff. Don't look at that. Like, that's who I am. You know, like, we look in the mirror and we go, That's who I am. Like, you see the person look, my nose looks like that. This is the way my hair grows on this tall hat. Yeah. Okay, that is you, right? But the shyness, that's not you. That is temporary. And I don't think I knew that when I was learning all this stuff. So it is even if it doesn't seem possible. Try to trust, at least what I'm saying here because I promise you, I've been there and I've taken many people out of that. And so it's just a temporary thing. So instead of saying, I am shy, you might want to say I feel shy.

Connell: Nice. Yeah. The feeling isn't real. Feels just how you feel in that moment. And I was paralyzing, like shy and introverted back in the day. And it sounds like you were too in your own way. So that's a great one to end on a trip. Before we go, tell us a little bit about the Tripp advice, and accelerator coaching, and also tell us how we can contact you if somebody is interested in working with you.

Tripp: Cool. Well, the way to contact is going to Again, that's And if you want to get coaching, we have a team of coaches because obviously, I can't do it all myself. We have a lot of people who want help and so we have a team of coaches ready to help you in a one-on-one program. So you get lots of attention and we help you with everything from completely redoing your online dating profile that's going to get you more matches. I know we didn't talk much about that today, but we do have a system that I learned over time. Once online dating did get more popular and tested things out for many years to see what works and what doesn't. We have that down to a science. We help guys and there is no guy. We've not been able to get tons of matches and tons of dates. That's for online dating. We also help you, of course, by going out and meeting women in person. We have strategies and formulas to help you get over approach anxiety, and different scripts to use that are not cheesy or weird or pick up to help you meet any woman anywhere at any time. And we've got guys to the point where they've I mean, anywhere from guys who have lost their virginity while working with us to guys who are, you know, 55 years old and divorced. And we've gotten them back in the scene and getting girlfriends, multiple girlfriends. So there's no one we can't help get coached by and we can assess the situation and see if you're a good fit for the program and go from there.

Connell: But can you help me get Tom Green's ex-wife, Drew Barrymore?

Tripp: Okay. There's one thing in this world I can't do. And that and that's the one.

Connell: Drew. It's not going to happen. All right. My Quest continues. Drew Cramer, thank you so much for being here. Check out Tripp's podcast, How to Talk to Girls. It's really good tons of great practical advice and TripAdvisor dot com he's basically everywhere. Trip thank you so much for being here amazing stuff.

Tripp: Thanks, Connell thanks for having me. Your podcast is awesome. I wish you so much success and Yeah Men! I appreciate it.

Connell: It was today because of you. Thank you. All right. Until the next time, I'll see you guys be authentic later.

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Dating Tranformation with Connell Barrett

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.

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NYC Dating Coach Connell Barrett

106 W 32nd St, New York, NY 10001

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