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How to Make Dating Fun & Get More Dates NOW

Featuring NYC Dating Coach Connell Barrett
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Learn how to make dating fun and get more dates in this episode of the Dating Transformation podcast.

Rejection… ghosting… not knowing what to say… low confidence. Man, dating can suck! But it doesn’t have to. What if you had simple, tested moves to not only flirt with wonderful women, but to also ENJOY dating?

It’s true—looking for love can be fun! In this episode of the Dating Transformation podcast, dating coach Connell Barrett shares his “happiness blueprint”—a new way to have fun on the singles scene, whether you want more matches on the apps, flirty conversations with desirable women, or steely self-confidence when you talk to your crush. Listen now and learn how to make dating fun. Give women what they REALLY want: a feel-good experience with your most attractive, authentic self.



“Hamlet said, the play's the thing. But in dating, the thing's the play: the fun, playful, good vibes. Women love a fun, playful man."

-Connell Barrett

"Taking action and enjoying the process is the key to achieving better results and staying motivated.”

-Connell Barrett

Featured in the episode

Connell Barrett

Founder and Executive Coach of Dating Transformation




00:00 - Introduction

01:31 - Transforming Dating into a Positive Experience

03:41 - Nurturing Love: The Journey of Becoming a Couple

06:47 - The Art of Letting Go and Going with the Flow

08:30 - Shifting Mindsets: Finding Beauty in the Dating Journey

10:47 - Domino Effect: Abundance Through Playful Dating

13:24 - Building Skills and Confidence in Dating

15:32 - The Transformative Impact of Breakthrough Moments

19:11 - Choosing Meaningful Love Connections

21:01 - The Road to Self-Discovery and Connection

25:32 - Fun Approaches: Unleashing Confidence and Joy

29:54 - Sparking Chemistry: The Art of Playful Dating

31:13 - The Playful Edge: Unforgettable First Date Strategies

33:01 - Outro

This show is part of the Spreaker Prime Network, if you are interested in advertising on this podcast, contact us at

Related episodes:

How To Flirt With Women

Dating Confidence

How To Get More Dates On The Apps




You can walk over to a woman and say, hey. My dad is Vladimir Putin. And that can work. It's amazing what can work.


Connell Barrett:


Welcome back to the dating transformation podcast. I am your host, and dating coach, Connell Barrett. I'm here to help you learn to flirt, gain confidence, find an incredible girlfriend, and listen to my Sonorous tones, my podcast voice, Here it is. Hey. Welcome back to today's episode. And today is all about Maybe. Maybe. For you. The biggest game-changing tip I can give you. which is how to make dating feel good and fun for you. this might be, you know, other than becoming truly radically authentic, which is what everything I teach is based on. Maybe the second most important thing in dating is feeling good. having fun with the actions you're taking. Because if you feel good, you're gonna take more action. If you take more action, you're gonna get results. And if you're feeling good, guess what? That woman you approach is probably gonna feel good. The date you have is probably gonna feel good, and you're also gonna have a lot of motivation. Let's be honest. The reason why my book is called Dating sucks, but you don't because for most men, probably for you, dating sucks. It hurts. It's painful. Rejection, approach anxiety, loneliness, looking at other guys and seeing them with incredible women and your own porn, Keeping you born in business. No judgment. No judgment. I visited that site myself. Anyway, let's talk about how we make dating feel good because, actually, let me start with a story. I wanna go back in time to a night when a great insight struck me on a night when I was actually striking out with girls. So back on May 25, 2011, My fortieth birthday, I went out solo to what is arguably New York City's hottest club. a spot that's harder to get into than Harvard. And that night, it was packed with stunning women in tight, tiny dresses. And I approached a little bit. Nothing really clicked, but I was taking action, and I didn't mind I was in really great spirits because first of all, it was my fortieth birthday. And I was dis I decided I'm gonna have fun tonight turning the big four o. and it was a night for me to pause and just appreciate how far I had grown. At that point, I was about 2 to 3 years into my working on myself, going from introverted and nerdy and dateless to taking action learning about flirting, approaching women, and working with a bunch of coaches, some of whom helped me immensely. So I was about two and a half, three years in. So I started at about age thirty-seven. And also at that time, I was, hey. Just began dating a wonderful young woman named Carrie. Carrie is a bright beautiful graphic designer, and we had just begun dating. It was early, so we weren't exclusive, but I was feeling really good about it. I was feeling really hopeful and full of gratitude. And turns out we ended up becoming a couple and had a really great relationship for several years. It did end, but it was a wonderful relationship. And so what I did that night is I changed my plan. I said, you know what? Don't make tonight about approaching or getting results. Don't in other words, don't be so agenda driven. Instead, I told myself, I want to focus tonight on enjoying this night. I'm gonna decide to have fun on some different terms. And as corny as that may sound, what's fun for me, or at least what was especially fun for me that night, is contributing to making other people's nights better. So instead of approaching women, I decided to simply share my good vibes. with those around me, essentially become a source of giving a source of good emotions. Good vibes. I had a good human vibe.


I'm gonna 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 freeze 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 pickup art. He unlocks your most confident self. so you can make authentic, romantic connections. For your next steps, book your free call today. At the 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 and transform your love life.



So, I remember I stopped, like, quote, unquote, approaching women. And, I remember I fist-bumped, a really well-dressed husband and wife. I said, hey. I like the threads, guys. I just started chatting with them, just being social. And we got to talking about theater, and they actually turned me on to an improv community. in New York called the magnet that would enhance my life for years to come. The magnet theater is where I've done improv for over a decade. And so that brought a lot to my life. Next, I remember I befriended a whole table of these fun, loving Australian guys. the birthday party. These Aussies had all come to New York for one of their birthdays. And I remember one of them even said to me, oh, wait, mate. How do you talk to girls so easily? Obviously, I have a terrible Australian accent, but he said, oh, hey. How do you talk to girls so easily, mate? And so I gave him some tips. and then I saw this really attractive brunette walking by. So I emotioned her to come to the table or the Aussie dudes and I were all hanging out. And I motioned her over, and she walked right over and I started to introduce her to the Aussie guy. And soon, she and the Aussie guy were hitting it off. Like, she loved his accent. I remember thinking, man, this coaching stuff is fun. That's actually one of the first nights I'd begun coaching, albeit for free, just for fun. And I remember thinking, wow, it's really fun to be a wingman. God, this feels great. And, in short, what I did is I let go of chasing what I wanted. And instead, what I did is I was trying my best to give to others what they wanted. So it was my fortieth birthday, but I was the one handing out gifts. It felt so good because after 20 years of dating, or I should say hating dating at that point, I finally loved it. And that it's that very enjoyment of the journey. that helps to create the results we want, the connections, the success. Now that enjoyment doesn't happen. It doesn't mean results every night, but definitely in the long term. And it actually increases your chances of having a really successful night. So it's a bit of a paradox. When we go out, to meet women, socialize, say, approach, or even go on a date if we go out with an agenda. if you go out making it all about what you want, then you're not gonna enjoy it as much unless you get the result. but that creates a real outcome dependence. And also it's a selfish or self-interest, purely self-interested mindset. It's much better to go out, finding ways to enjoy dating that are not related to that woman liking you. Even though we want a beautiful, incredible, wonderful woman to like you, we don't wanna be dependent on that. So to get better at dating, I want you to find ways to enjoy dating better. Fall in love with the process. make it feel good and share those good feelings with others. because, man, it's all about the feels. It's all about the feels. So let me try to break it down this way. When dating feels bad, you take little or no action and your confidence sags, and then your love life sucks. But when the process of dating feels good, then you take tons of action, your confidence source. And pretty soon, you're starting to attract the kinds of women you want. and this applies to so much in life. If something feels good, you do more of it with your whole heart. Anything that you value, and that you enjoy pursuing, you're gonna do it more often, and you're gonna get better at it faster. So pop quiz. Think of a rewarding hobby or passion that you have that you love to do this thing. What is it? I'll pause for 5 seconds while you think, and I'll play the Jeopardy theme song while I do it. Okay. What is the thing you love? What in other words, lights you up more than anything? Maybe it's traveling, maybe it's physical activity, a sport you play, maybe it's working out, maybe it's playing guitar drums, whatever this thing is that you love to do, the reason why you're so motivated by this thing is twofold. number 1, because it's good for you, and number 2 because it feels good. It's playtime. It's not work. It's play, and that's what keeps you coming back. I forget what work it was of his, but a character in a Shakespearean play says, oh, wait. It was Hamlet. Of course. It was Hamlet. So in Hamlet, there's that famous line that plays the thing. Well, in dating, the thing is the play. playing fun, playfulness. These are irresistible vibes to women. So if you have more fun, if you feel good, then you're gonna get the girls. But more importantly, a playful approach to dating will light you up feeling good will, like, will light you up because you'll take action until you reach the dating outcome you want, the relationship you want, the confidence you want, So here's my vision for you. My vision for you is to take a lot of action and have as much fun and feel-good moments as you can because when you have fun with dating, what happens is you tip over a domino that starts a chain reaction. I call this the upward spiral of abundance, and it goes like this. So you start to take action, and you're all excited about the outcome, right, the goal, the relationship, the love, the sex, all that good stuff, and that feels really good. You start moving toward it and you get momentum. Momentum feels good. This leads to more action and more confidence. That feels good. And you also start to numb yourself to things like blowouts or ghosting or disappointments. and you realize that they really can't hurt you. k? And this leads to more action, more good mojo, And with all the reps you're getting, you know, you're flirting, you're approaching, you're asking out your crush, you're texting, you're swiping on the apps, you get better and better. And then you meet more and more women, and then you just keep improving your skills. You meet more women. You get bolder. you start taking more chances. You start doing some really, it's you do really great some nights, some days. other nights you fuck up. That's fine too. There's no harm in making mistakes. That's all part of the process, and it's all good. You're truly enjoying the journey, and then it happens. You have a breakthrough. you have an experience that blows your hair back. Like, the big blowback experience, it was The first night I ever went out approaching women, and I met this incredible girl named Kelly. I talk all about it in the very first chapter of my book. That was my breakthrough moment. But yours is gonna be yours. Yours will be different from mine. Maybe you make out with the most beautiful woman in the bar. or maybe you have a date where you never run out of things to say. And everything you say is flirty and funny and authentic and in the moment. or maybe you're out and you, you see that gorgeous wow girl. And you walk up, you approach her, and you have no fear. It's as easy as walking up to somebody to ask for directions, but instead, you walk up and you say, hey. What's up? I wanted to meet you. You're adorable. and she is super into you. or maybe you launch a profile. You finally launch that profile. You get the right photos. You get the right Bio, and then, boom, your phone fills up with matches. You'll know what the breakthrough is when it happens. k? Every guy, at least every guy I work with has that big breakthrough moment. And when that breakthrough happens, then you're gonna be so full of confidence, and then you'll get that hard evidence, that proof of your worthiness, and then you're gonna truly realize in your marrow that I am enough. I am valuable. Lots of wonderful women like me. I'm good. And this epiphany unlocks a sense of abundance, both in the raw number of dating options you have, but also what's called an internal abundance, which is that endless, stash of self-confidence and you realize that, hey. You're in any woman's league and she'd be lucky to have you. And if she doesn't want you,


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 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 audiobook. Getting dating sucks, but you don't today. To transform your confidence and find your dream girl.


If you get ghosted, if she goes quiet, that's fine. You have 10 more great options here. And, but that freedom from outcome, this positive, confident, authentic energy, loving, confident, just so incredible. This energy actually makes you even more attractive to women because you're not needy. You're not agenda driven. You have more to offer and 0 neediness. And then that strikes you up to take even more action, makes you even more attractive to women, and the upward spiral continues. And then you ride this momentum until you meet a girl, truly deeply connected with who is a really incredible quality woman, quality, wonderful girl. And then you're able to choose a great partner from some wonderful options. You want to get to that point where you say to yourself, you know what? Allison was a fun fling. And Jennifer was a man, she's a good kisser, but I don't know. I just don't see myself taking her home to meet my parents. But you know what? There's something about Erica. I think she's the 1. And then you get to choose her from some nice options. you get to settle down instead of settling 4. This is how I met my girlfriend, Justin, and She's a beautiful, incredible, wonderful woman. She could have had any number of thousands of guys in New York City. Hell, millions, probably. But she chose me. I could have had, maybe not a 1,000,000, but any number of wonderful women, but I chose her because we click, we connect, we fit. and that same destination awaits you. but to reach it, you need fuel. You need fuel in the form of -- feel-good, fuel, fun playfulness, and enjoyment. In other words, you need to love the process or at least not hate it. You need to start enjoying the process. so, yeah, you wanna find ways to enjoy dating on your terms. understand how to do it, and that will make dating a feel-good experience. get to that point where you say, hey. You know what? It feels good to share honest vulnerable truths with women. That feels good. feels good to hang out with your favorite wingman, crack jokes together, and be on the journey together. Feels good to send silly, witty, weird Tinder openers that crack you up. Feels good to have predated butterflies. Feels like it means you're alive. It means you care. feels good to accept yourself as you are right now in all your enoughness while still working on yourself and improving yourself. It feels good to be free of rejection. I'm sorry. Free of the fear of rejection. And to not even see rejection as a thing that doesn't even exist. at least not in the courtship phase. It feels good to grow as a man to give to a woman. It feels good to share your romantic intentions with good intentions, right? It might be scary, but it also feels good to walk up to that stunner and say, hey. You are super cute. You're totally my type. I wanted to meet you. Oh, it feels good to hand your car keys. The car keys of your love life to that high what I call the higher self, that true badass authentic best you, And, yeah, it just feels to know that you're enough and to just strip away the doubt, the fear, and just drill down to your core. and revealing that diamond beneath that diamond inside of you, that authentic man of confidence, action, courage, empathy for women, respect for women, but still just being so badass and attractive and magnetic. Feels incredible. So we wanna make dating a feel-good experience. So here are a couple of thoughts about how you might do this. More practical thoughts. This is apples to oranges, but let me talk about my tennis game, and how I went from hating my tennis practice to loving my tennis practice. So I've been working on my tennis serve. And you know what? I hate spending an hour just hitting mindless tennis serves over and over again. That bores me. I don't like doing it. And if it feels bad, I know I'm not gonna do it. So what did I do? I went out. I did some googling, and I found some really fun drills and games, where I now go to the tennis court, and there's a drill where I have to make 10 straight first serves And if I miss any serve on the way to 10, then I have to go back down to 0. I play that game. I also play another serve game. It's a second serve game, where I do second serves. I'm by myself on the court. And every time I make a second serve, it's a point for me. Anytime I miss a second serve, it's a point for my imaginary opponent. And All of a sudden, my brain loves practicing serving because I like to play games. I like the challenge of a game. I like the fun. I like that it's like you're pouring your actions into the container of a game. Why am I talking about my tennis serve on a dating podcast? because you have your own blueprint for what feels good, what makes you happy, what will make you smile, and what will make your brain smile. And everybody's blueprint's a little bit different. So you wanna ask yourself, how can I enjoy dating more? What specifically can you do that's in your control that you'd completely control, that will be fun for you? We don't wanna get attached to 2 outcomes of a woman needing to like us. Don't get me wrong. Of course, I want that cool, cute girl to be all over you, and you're all over her, and you're just loving each other. But we don't wanna be dependent on that. I don't wanna become a validation addict. That's no way to go through your dating life because that gives all your confidence and mo good emotions away and puts them in her hands. And women don't like it either. Women don't wanna be with a needy guy who has to have her like him. So what we wanna do is come up with ways that you will find enjoyment and specific actions. or thoughts too. It can be a thought as well. It can be a context that you change because think about me and my tennis game, I'm still doing the exact same thing. I'm going to the tennis court, and I'm serving. But my old mindset was, let's go hit serves for an hour, and I hated it. My new system is to play these serving games. And all of a sudden, the hour goes by in no time. And I'm in a flow state, and I'm getting better at tennis. My serve is getting better, and that feels good. So let's talk about ways we can do that. Let's talk about approaching for 1, one context is approaching. How can you enjoy approaching? Other than every woman you approach likes you. Guess what? That's nice, but it won't happen. How can you enjoy approaching? You can play some games. create some challenges, go out with your Wingman, or get a Wingman and play a game. You could play the game where I used to do this with my old wingman, where I had to approach any girl he pointed to. and he had to approach any girl I pointed to. We basically take turns becoming each other's coach. So you could do that. Some of my best approaches and some of my best outcomes came from my wingmen back in the day saying, okay, Connell. See that see that cute blonde and the sexy brunette, and that dude sitting over there, go over there and approach. I never would have gone over there. but my wingman made me or not made me, but I agreed we were gonna play the coaching game. So you can play a game of coaching your friend and vice versa. Another fun game you can play is, to give yourself a very specific and strange word that you have to say in your opening opener. with what you say to a woman. So, I was with a client once, and I said, okay. See that girl over there? You have to go over there. And whatever you say, you have to include the name Vladimir Putin. And he walks over. I couldn't hear the entire opener, but he said something like, oh, hey. Did you know my dad is Vladimir Putin, and she started laughing. And he was laughing. He was having fun as he approached a woman. guess what? What I love about that stupid little exercise is not only is it fun, but it reminds you of the very powerful lesson that the words you use when you approach don't matter much. as long as you're having fun and you commit to it. And you can walk over to a woman and say, Hey my dad is Vladimir Putin, and that can work. amazing what can work so you could give each other. You could give yourself a very fun, silly secret word you have to say. just to amuse yourself when you approach. One more approaching tip is the karaoke opener. I love karaoke. I'm singing karaoke tonight with my girlfriend. And, what you could do if you're a karaoke fan, you can walk up to a woman in a bar, in a club, And you can just sing the first few words of your favorite karaoke song. My client Ken and I went out once. with me as his wingman. And we were in this bar in New York City, and I and I pointed to an attractive woman he wanted to meet. And I said, okay. What's your favorite karaoke song? He said purple rain. I said, great. Off you go. sing the first few words to purple rain. So Ken walks over and He commits to it just like it's karaoke night, and that's half the battle really committing to it. And he walks over and he points at her and says, I never meant to cause you any sorrow. I never meant to cause you any pain. Does the first line of purple rain? She starts singing the song with him. They're basically next thing you know, they're doing a duet of purple rain. And minutes later, their fingers were intertwined. They were all over each other. All because he found a way to make that opener fun and enjoyable for him. Felt good. And because it felt good to him, it felt good to her. So those are some strategies for approaching this. For 1st dates, How do we make 1st dates fun? Play games. I love doing steering contests with my clients. I mean, I have them do steering contests. You're on a date. and you're half your half hour in and you just say, hey. I have an idea. Let's have a staring contest. Your game will be played for a drink. You can make it a wager up the stakes a little bit. Let's do a steering contest. We keep eye contact, you say to her, We keep eye contact. Blinking is allowed, but no laughing and no looking away. And then you challenge her to a steering contest. This works so well because first of all, eye contact is really sexy. People that are part of connection and attraction are just deep eye contact. So this gives you both permission to stare deeply into each other's eyes, which women love. Also, of course, What happens when you say no laughing allowed makes it all the easier for her to wanna laugh? because all of a sudden, we're trying to stifle the emotions. Right? You might struggle with it too, but that's okay. So all of a sudden, you're both laughing or at least trying to restrain a laugh, which is really fun. And also if you win the steering contest, You can trash talk. You can tease her with a joke and say, oh my gosh. You're terrible at this. Why do I always go on dates with girls? Who can't win a staring contest? My little niece is better than you. Anyway, so you can play games on 1st dates like steering contests, 2 truths in a lie, you can well, there's a whole but there's a whole bunch of games that I talk about in my book in the first chapter. So if you want a whole list of fun first date games, then off you go. But, yeah, so here's my marching orders for you, dear listener. sit down and write out a list of what I call the feel-good list. Sit down and write out at least 10 ways you can do 10 things you can do or think or focus on that feel really good. I call this the feel-good list. In other words, you can have fun in your dating pursuits that are not dependent on that woman liking you and having a date with you kissing you. Those things will feel good when they happen, and I hope they happen to you very quickly and often. I hope they already are, but we just don't wanna be dependent on them as men. We don't want to be dependent. on that validation. We wanna find the fun, find the validation inside. So, yeah. and Hamlet said the play's the thing, but the thing is really the play. Play fun, and feel good. That's what makes dating fun. Fun equals action, action equals results. Alright. That is the end of today's solo pod. Thank you so much for listening. Remember, your ideal woman is out there. Your dream girlfriend is out there. She already likes you. She just has to meet the real authentic you. See you next time.


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


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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.

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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