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Risk-Taking in Dating and Love: For Instant Confidence, Become a Bold Risktaker

Featuring NYC Dating Coach Connell Barrett
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Risk-taking in dating and love is an important step in getting what you desire. In this episode, Connell Barrett shows men how to be a confident risk-taker who women love.

Odds are, you’re making a BIG mistake with a woman and you don’t even know it: You’re playing it safe. Being timid. Not going for it.

Sure, you’re a nice guy and a true gentleman, and you don’t want to “creep women out.” That’s a good thing! But if you play it too safe in dating, you convey low confidence or come off as boring. And this repels women. Why? They don’t want a safe, timid guy. They want a confident risk-taker. Hello, friend zone and rejection and loneliness.

Never fear—dating coach Connell Barrett is here. In this episode of the Dating Transformation podcast, Connell shares some simple secrets to being the kind of bold badass women ache to date… no weird pickup tricks needed! Listen now, to go from playing it safe to confidently attracting wonderful women. Risk-taking in dating and love is on your to-do list. You’re about to become a Romantic Risktaker.



"Playing it safe is great for buying stocks or choosing a doctor. But if you want to attract incredible women, you must become a risk taker."

-Connell Barrett

Featured in the episode

Connell Barrett
Founder and Executive Coach of Dating Transformation


00:00 - Introduction
02:54 - Unlocking Connection: The Shift That Made All the Difference
07:04 - The Transformative Power of Commitment in Love
08:07 - Building Connection Through Giving and Asking
09:32 - Playing the Full Game: What LeBron Can Teaches About Love
11:42 - Learning to Lead with Assertiveness
13:53 - Piloting Through Love: The Highs and Lows of Risk
15:42 - How to Stop Overthinking and Start Approaching
18:11 - Why 'Risking It' Is Your Safest Bet in Dating
21:08 - The Cost of Not Taking the Next Step
23:40 - Authenticity as the Ultimate Risk: When Being You Pays Off
26:27 - Outro

Produced by Heartcast Media

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Related Episodes:

Are You Man Enough To Be Feminine

How To Go In For The First Kiss

Stop Getting Ghosted

How To Charm Women




I didn't have any assets. I used my whole ass. What little of it there is.


Connell Barrett:


Welcome to the Dating Transportation Podcast. Here's your host, Dating Coach, Connell Barrett.



Welcome back to the Dating Transformation podcast. I am your host, dating coach, Connell Barrett. I help men who are introverted. or just nice guys who have never really cracked the code on dating. I help guys like you, in other words, learn to flirt, gain confidence, and get a great girlfriend. And all by being authentic, being real, natural, genuine, what I call no pickup artist tricks. No surface level stuff. We're talking about true inner and outer change and success, because that's the best way to do this whole dating thing. And I wanna ask you a question. Have you ever approached a woman or just had a conversation with an attractive woman, and you could feel yourself playing it safe. You could feel yourself thinking, okay, don't mess this up. don't say the wrong thing. Say the right thing. don't be creepy. say something cool and edgy maybe something I saw on some YouTube channel, being an alpha male, and it got you in your head. And you could feel yourself basically walking on eggshells with this woman. especially when you're out socializing and meeting new people. And chances are if you felt like you were being really safe and it created nerves. And I'm gonna assume that it didn't lead anywhere. didn't get a phone number. You didn't get a date. And you just walked away from that approach or that date or that situation thinking, oh, man. That didn't go well. I don't feel like I created that spark with her. I came across as either boring or she just wasn't that into me. So if you've ever felt that way, then I wanna help you break through that and help you become a confident authentic risk taker. And taking risks, romantic risks, it's very important that you understand how important it is to be a risk taker in the area of women and dating, especially with approaching. Here's a quick story. I was out last Friday night, with a handful of clients here in New York City. So what I do is every couple weekends, I go out with my guys, couple clients, and we approach women together. My clients walk up to beautiful women in bars, coffee shops, and cool lounges. So last Friday night, I was with a couple of clients. And my client, I'm gonna call him Lawrence. Lawrence was seeing these beautiful women walking around this lounge on the lower east side of Manhattan's really cool lounge, just filled with beautiful, cool, interesting, stylish women. And I saw him approach a girl, and he walked over to her and his body language was tentative. He said something like, oh, hey, don't wanna bother you, but I just wanted to come over and say, hi. Like, his voice went up, like, up talking. And, He just gave off a vibe that showed it was very in his mind, it was very safe. Okay. I don't wanna I don't wanna freak her out. I don't wanna scare her. So he walked over, and he was very safe. And she talked to him for about 20 seconds and then politely basically turned away from him and went back or talked to her friends. And I went right up to Lawrence, and I said, go back and re approach her. He's like, what are you talking about? She said no, or she, no, she's not interested. I said, she's not interested because you're coming across, like, a safe, I don't wanna say nice guy because I like nice guys, but, like, a safe guy who feels unworthy of her. So walk back over there. He went up a second time. And the second time he went over to her, she responded better, actually. And he stood up taller, and I said, I want you to make this feel risky. So he walked up. He was much more direct to her. And he said, oh, hey. I just wanted to come back and talk to you some more because you're really cute. And all of a sudden, she responded the way we want women to respond. She said, oh, really? Well, you're just really confident are you, and they had a really nice conversation and interaction. So that second time The first time he went up, he made a big mistake, a common mistake, but a big mistake, which is that he was playing it very safe. Let's call that 70-65 percent commitment. He wasn't really committing to the


I'm gonna read your mind. Ready? I'll bet that you would love to confidently approach women. Get great matches on the 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 on 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 help them attract the dream girlfriends. So book a free strategy called today to see if Connell's coaching is right for you. On your call, Connel 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 pickup artist tricks. He unlocks your most confident self so you can make authentic, romantic connections. Your next steps: Book your free call today at and grab a time that works for 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 act and transform your love life. Bye.


The second time with my coaching and help, I made him stand taller, look her in the eye, take a more unapologetic sort of a vibe and just look her right in the eye and say, hey. I wanted to come back to you. You're really cute. And I, I wanna talk to you. And just the power of looking at a woman in the eyes and saying, hey. You're interesting to me. I want to get to know you. That's a risk that feels riskier, but it's actually a smarter, safer strategy. So how do we become a risk taker in approaching women, especially? Well, Bottom line is I wanna share with you what I talk about in my book. I call it the paradox of approaching. which is that what feels safe is actually really risky and what feels risky is actually really safe. I believe I had 1,000,000 coaches back in the day, but I believe I got this concept from my old coach, Owen, Owen Cook. who has probably approached more women, than any man alive. I would wager. Anyway, I think this comes from Owen. I just like to give credit, what credits do. So here's the concept of the paradox of approaching. So when you go out to approach women, You must fully commit. You know, she needs to hear you and see you. I don't really care if she likes you or not. you just wanna make sure she reacts to you and sees you as a confident risk taking man. So you're doing it right. By it, I mean, approaching. You're doing it right if it feels a little bit risky. And I want you to follow that feeling. Now the paradox is an approach that feels, quote, unquote risky is actually safe. Safe in the sense of giving you a good chance for an outcome connection with her because full commitment is how we get results in life in general. I mean, think about it. Think of the way Jack Nicholson would commit fully to a role. Think of the shining. He commits fully to being this crazy character who's gone insane and is trying to kill his family. If he had not committed to that role, if he was looking at the camera and kinda winking and and just not committing, it wouldn't work. but he committed to it. Or think Michael Jordan or LeBron driving to the hoop. Right? How many times have we seen LeBron just freaking take it to the hoop full bore. Usually, he either scores or gets a foul. But, hell, even if he fouls, even if he commits a charge, at least he freaking committed to it. If he didn't commit, he wouldn't get the slam dunks. He wouldn't score as many points. So commitment is something we need in life in general. On the flip side, a quote, unquote, safe approach is actually very risky because you risk that it likely won't work. So I remember when I had this big epiphany, I was out approaching women over a decade ago. And I saw this beautiful brunette in a shiny silver dress at a rooftop bar in Lower Manhattan. And I I was playing around with this idea of, woah, do the committed thing. Go all the way. instead of tiptoeing around this. And, I walked up to Bree, or, I mean, I didn't know her name at the time, but I walked up to this woman, And I said, oh, hey. What's up? I'm Connell. I just saw you, and you were totally my type. yeah, she reminded me of, she looked like I think I might have even said, you remind you look like you're totally my type. You remind me of Jennifer Beals from Flashdance. Flashdance is a movie from the eighties. If you're not a thousand years old, you might not know this movie. But, basically, I walked up to Brea and I said, hey. You're totally my type. You remind me of flash dance, the girl from flash dance. She laughed and threw her head back. And I was standing, I looked her right in the eye, shoulder to shoulder posting up. oh, I also said to her, I'm a and I'm actually pretty shy. I don't usually just walk up to women, but I had to come up and say hi to you because you're like the flash dance girl. And so I was vulnerable at the same time. So I was really being genuine and real. but I was committed to it. I didn't have half the assets. I used my whole ass. What little of it there is. Yeah. my ass is so flat that when I half ass, it's, like, really 1 5th asking it. compared to most people. so, yeah, remember, with approaching, what feels risky is actually safe and what feels safe is actually risky. So back to Lawrence, went out with Lawrence. I mean, we went up to some more girls. and these two girls walked by us on the way to a different part of the bar. And he followed my directives. He immediately walked after them, got up alongside them, tapped them on the shoulder and said, hey. Stop. I need to talk to you too. And they stopped instantly because he fully committed, and they got sucked into his magnetic force. And all of a sudden, Lawrence had this major breakthrough. He realized, oh, gosh. When I approach with that safe, half hearted, walking on eggshells energy, women just basically would swat him away like a mosquito. But when he went up forcefully, But with empathy, by the way, I'm not saying be some asshole, or or be like some toxic dude, Hell no. I am saying it's forceful. I should say, maybe assertive is a better word. It's assertive, and it's positive. I'm expecting it to go well. So Lawrence rolls up to these 2 girls, taps him on the shoulder, he's smiling, and with a positive assertiveness, He says, oh, hey. I had to talk to you too. You guys are freaking cute. Who are you? What are you doing? And then all of a sudden, they're like, who is this guy? Oh my god. You're so confident. You just came right up to us. So that's an example of an approach that would feel risky at the moment. but it's actually safe and smart. So, again, what's safe is risky and what's risky is safe. The analogy that Owen used, I believe, back in the day when approaching this paradox is, imagine you're flying a plane, and it's your 1st day as a pilot. your first day on the job as a full time pilot and you are piloting a jetliner, it would feel a little bit risky to take that jet up too high, too fast. Right? So your brain might wanna say, oh, fly nice and low and safe. But guess what? what's low to the ground when you're a pilot. mountains, buildings, things to smash and crash into. So that's counterintuitive. Instead, what you wanna do is get that plane up to 30000 feet. as relatively soon as you can because that's how that's how, planes work. You see the limit of my knowledge of planes But, anyway, now flying up to 30000 feet would probably feel pretty scary the first time you're doing it as the pilot of a plane. or maybe just the first time you're flying, but guess what's up there that high? That's where it's safe because there's no other there's no buildings. There's no mountains. There's fewer planes. So I really like that analogy that Owen used. Basically, think of approaching like you're flying a plane. Don't go low to the ground. That's where the buildings and mountains are to smash into. Fly it really high. get up there as high as you can, and you'll be in a really good place. so, yeah, some examples of safe versus risky, just to give you a couple of real world examples. So what safe would be say seeing what I call a wild girl, right, seeing a wild girl, out in the world, which happens all the time, probably to you, you see a beautiful woman at the gym, or at the bar, and you think, So safe would be seeing that girl and trying to think of the perfect opener, getting in your head like, oh, what's the right thing to say? What's the perfect opener? What's the cool line from the YouTube guru who's full of shit. Doesn't know what he's talking about. that's safe. and then she walks away and you never talk to her. Right? Or another thing that's safe is, you know what? I'm not in the mood right now. I'll do this tomorrow when I'm in a better mood, when I'm in a better mood, feeling more confident. That's safe, and that means you're not gonna get that girl. What's risky is you'd walk right up to her and you say something, anything that enters your mind,


Rejection, ghosting, loneliness. lack of dates and lack of confidence. For many men, dating just sucks, but it doesn't have to. There's a simple yet powerful way to gain instant confidence and attract a great girlfriend. Be radically authentic. It's all laid out in the number one Amazon best selling book. Dating sucks, but you don't. Your step by step guide to attracting wonderful women and doing it with total authenticity. Author and dating coach, Colonel Barrett, has had and fixed all the dating problems that you struggle with. He's also helped thousands of men gain confidence and find love. He's put his best tips and strategies into dating sucks, but you don't so that you can confidently approach women and get dates. Become magnetic and attractive. even if you're not tall or great looking. Always know what to say to make sparks fly. Get lots of great matches and dates on the dating apps and attract your dream woman. You can find dating sucks, but you don't on Amazon. or wherever books are sold in paperback, Kindle, and audio books. Getting dating sucks, but you don't today. To transform your confidence and find your dream girl.


Even if it's as simple as, hi. I just saw you and wanted to say hello. I can't tell you how many times I've approached a girl by having no idea the words that were gonna come out of my mouth. I just said, oh, man. I wanna meet her. Approach, say something, even just, oh, hey. I'll fill in your name here. What's your name? I wanted to say hello. so that's risky. It feels risky, but guess what? Risky is safe and smart. Okay? Another example of safety is safe if you break the ice with a soft whispery vocal tonality that creeps her out. Hey. Hi. Excuse me. Like, I was with a client a while back for the first time ever approaching girls. We wrote a bookstore, Barnes And Noble here in New York, and he, quite understandably. I get it, but he quite understandably walked up to this girl and, he was talking to her, like, Like, with this wispy voice. I mean, he sounded like a deep throat from all the president's men. yes. Yes. Hi. I just wanted to meet you. Also, follow the money, and we'll bring Nixon down. So He was trying to basically, he felt like, oh, it's the safe thing to do. I'll be soft and whispery. But guess what, guys? A soft whispery vocal tonality creeps girls out because it makes them feel like, oh, whoever this guy is, He doesn't have confidence in himself. So safety is opening with a soft whispery vocal tonality that creeps girls out. Don't have a deep throat. What's risky instead is using a clear loud resonant tone that makes her notice you. That might feel risky because you have to be louder than you normally are. But guess what? People in general, women in particular, people notice a loud, confident vocal tonality. So that's an example of what feels risky is actually safe and smart. Don't forget well, there's a simple vocal tonality rule I have in my book, the whole chapter about approaching women. where I talk about the right vocal tonality is wherever you are, whether it's a bookstore, cat, coffee shop, cloud club anywhere. What you wanna do is notice the baseline noise level of the environment. Check check-in with it. Listen to see what it is. And then make sure that when you approach your vocal tonality is about 3% louder than the baseline. k? Don't be 20% louder. Don't screamatter. but also don't be whispering deepthroat. Don't be like Holbrook in deepthroat or in all the president's men. Oh, man. I'm still dating myself. how old I am. I like old movies. okay. Another example of being safe is, oh, this is so common. Please don't do this. I beg you, is having a really great conversation where you're talking to her, and it's going good and she's liking you because who the hell wouldn't like you? You're awesome to her, and I know you're awesome in many ways. you're having a great conversation, and then you don't ask for the number. That's safe. Happens so often because you're trying to protect your ego and say, well, I don't want this to go well. I wanna settle for this good conversation. That's understandable, but it's playing it safe because not asking for her number or asking for a date means you will not get a date with her. So, that's safe. What's risky is going for it. The only way to get dates is to ask for dates. Gotta be you've gotta take risks. What feels risky? Quick story about this last one. I was out with clients several years ago before the pandemic. I was out with clients in a park in New York City. And my client, Joel, approached a beautiful , cute, attractive, stylish woman. Yeah. Cool. Sunglasses. She just looked like the cover of, I don't know, glamor magazine. She was dynamite and just look like, looks really classy and confident in addition to being really attractive. Anyway, I walk over. I'm sorry. I see Joel walks over, sits down with her. chats her up, doing great. and then I'll I'll leave him, go find my other client. And when I come back, Joel that the woman's by herself. And I'm like, oh, where's Joel? What do what happened? So I found Joel about sitting on a bench out of sight of her, and he's sitting on a bench and he's holding his face in his hands, like head head down face face in his hands. And I'm thinking, oh my god, what the hell happened? What did he do? and I walk over and I say, what happened then? And he said, ah, it was awful. I we had a great conversation. We talked for 10 minutes. I'm into her. I feel like she's into me, and then I just I just didn't ask for her number. I just said, well, nice meeting you. And he was, like, almost in tears. And I said, well, guess what? You can make this right right now because she's still sitting there. And then I asked him, here's my question for you. If if you could walk over there and say, the riskiest, true, non vulgar thing. You could say to this attractive woman, what would it be? What's the most honest, also risky, but also honest and real authentic thing you could say to her? And he said, you know what? I go back over there and I'd say, hey. By the way, I I should have asked you out before, but I got nervous because Beautiful women make me nervous sometimes. But you know what? I'd love to take you out. Can we would you like to go on a date with me? Those are his exact words almost. and I said, great. Go back over there and say that to her. So he marches back over I'm watching from about 15 feet away, 20, 25 feet away. So I can't hear exactly what he says, but he says pretty much what he said to me. and here's what I see. He walks over. She looks up. She's like, yes. You're back. Yes. He says what he says, and her face breaks out in a huge smile when he says that I wanna go out with you. I should have asked you before. And then I see her put her arm out, put her hand out to say, give me your phone. and she takes his phone and punches in her number, and then they're setting up a date. And then He came back to me. He was, like, 10 feet off the ground. He was floating. Joel was so that he now had a phone number and a date with the most beautiful woman in Madison Square Park. And all he had to do was take some risks and go back and say the risky thing instead of the safe thing. So that is the main lesson for today. Go out. Take some chances. Be vulnerable. Be authentic. Put your real self out there. Women love it. They wanna meet the real you. so become a risk taker. Don't play it safe. Life's too short to do that. Play it, play it with risk and empathy and authenticity, and you cannot go wrong. Okay. That's today's episode. remember, your future, amazing, incredible, awesome girlfriend. She's out there. and she already likes you. She just has to meet the real authentic you till next time.


Thank you for listening to the team transformation podcast. For lots of free tips, videos, and other goodies, go to See you next time

Get Transcription
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.

dating sucks but you don't #1 Amazon bestseller

Get this Book & Attract Your Dream Girlfriend


NYC Dating Coach Connell Barrett

106 W 32nd St, New York, NY 10001

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