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3 Dreaded First-Date Mistakes to Avoid, and What to Do Instead

Featuring NYC Dating Coach Connell Barrett
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In this episode, learn about the first-date mistakes you may not even realize you're making, and how to replace them with three simple moves to shift things in the right direction.

Do you struggle to make sparks fly on first dates? Do you think it might be “creepy” to go for a first-date kiss? Do you TRY to be funny and interesting and cool, but you fall short… and women just don’t want to have another date?

Let’s fix this!

In this episode, dating coach Connell Barrett shares the three most common first-date mistakes that you’re making… and you don’t even know it. He also gives you the RIGHT three moves to correct things. And he shares an incredible client success story, about a guy who went from the Friend Zone on first dates to FIREWORKS. (Your jaw will drop.)

Listen now, so you can start having fun, sexy, connected first dates… and do it as your most confident, authentic self.



"There's nothing wrong with fear, but there's something very wrong with cowardice. Sculpt a dating life of authenticity and courage, no cowardice allowed."

-Connell Barrett

Featured in the episode

Connell Barrett
Founder and Executive Coach of Dating Transformation


00:00 - Introduction
02:40 - From Struggles to Coaching: Connell's Dating Journey
03:53 - Busting First Date Myths: The Quest for Truth
05:19 - Flirting Dos and Don'ts: Avoiding Surprises
06:06 - Bill's Journey: Overcoming the First Date Struggle
07:11 - Transforming Your Dating Life with Connell's Coaching
10:22 - First Kiss Realizations: Making Her Feel Desirable
11:01 - Deciphering Women's Desires: A Constant Interest
12:39 - Embracing Courage: Transforming Dating Fears
18:55 - The First Kiss and Deeper Connections
20:18 - Debunking First Date Myths: Quick Insights
24:05 - Impressing Women with Authenticity: The Key to Success
24:54 - Outro

Produced by Heartcast Media

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Sober Dating



There is nothing wrong with fear, but there is something very wrong with cowardice.



Connell Barrett:


Welcome to the Dating Transformation podcast. Here's your host, dating coach, Connell Barrett.

Welcome back to the dating transformation podcast. I'm your host, dating coach, Connell Barrett. I'm here to help you learn to flirt, gain self confidence, And get a great girlfriend, a great partner, and do it with radical authenticity. Authenticity. Authenticity. Note to self. Start a secondary podcast, dental podcast, called authenticity authenticity. Anyway, I am sober even though I don't sound like it.


And I'm really psyched about today's episode. I'm just leaving that in. I'm just leaving it in. We all make mistakes in life. Sometimes, it's just hard to Clink thoroughly. Our brains don't work. Today, I have a really fun episode idea that I just came up with because It stems from a client success story. Maybe the single most insanely awesome first date Client success story I've had in my 10 years as a dating coach, and I'll get to that in a couple seconds. So here's the topic. The topic is we're gonna talk about the 3 biggest myths about first dates. The 3 things that you have probably thought, heard, or at least been told, and what to do instead. Basically, these are 3 common mistakes you might be making if you buy into these myths. And Hey. 1st dates are important, obviously. Any relationship has to start with the 1st date. Any fling, Any situationship, any f buddy if that's your dating flavor. No judgment here. It's gotta start with a 1st date or a 1st encounter or 1st hangout. Call it what you will. And if you don't get the 1st date down Well, then you're gonna lose out on some opportunities. You're gonna miss out. Take it from me, A guy who struggled on 1st dates a lot back in the day. The reason I became a dating coach is because I used to be terrible at dating. I was in the friend zone. I struggled on 1st dates. I really struggle with my dating life. And it was only after I fixed all these problems and learned how to fix them in myself and then others that I became a dating coach. So every time I talk about a problem, every time I talk about something that's not working in your dating life, guess what? I've been there. I struggled with it. I had it, and I fixed it. And I remember really struggling with my 1st dates back in the double z mid the mid double zeros was when I I'm single. I was newly single, called off a planned wedding that I did not wanna go through, And about, 2 months before the wedding. And then I said, alright. Time to become single. And I started going on some dates, and Most of them didn't go very well. I rarely was able to create the kind of spark and connection with that given girl, that given woman I wanted to. And I got a lot of help, and I figured it out, hey. Here's how you flirt. Here's how you connect. Here's how you Channel your sense of humor so that you start having some nice, fun, sexy dates. And along the way, I started keeping a list of what I thought was the case in dating and first dates and what the actual truth was. Sort of a myth list. Had this myth list. And so let me talk about this first the 3 of the most prevalent first date myths and what you should do instead. And myth myth number 1 is this, the idea that You cannot go for a 1st kiss or quote, unquote escalate without it being creepy. A big myth I hear from guys is, oh, I don't wanna go for a 1st kiss. I don't wanna make a move. That's creepy. It's wrong. It's inappropriate, especially now that we're in the me too era, an era that I completely agree with and I'm happy that we're in. But a lot of guys are really in their head about 1st dates, and they think, oh, man. It's just not right to go for a 1st date. I'm sorry. A 1st kiss on a 1st date, And that's a total myth. And the truth is you absolutely do want to go for a first kiss. At some point, if you and she are vibrating relatively well, She's paying attention to you. She seems to be enjoying your conversation. And ideally, if you flirted a little bit beforehand, You don't wanna surprise her. You don't wanna lunge at her and try a 1st kiss out of nowhere. But if you've given her some signs and signals that If you're interested, if you flirted, then going for a 1st kiss is absolutely a great idea, at least for a nighttime date, especially if it's a date where there's some alcohol involved or it's just a nighttime fun nighttime setting. If you have a quick 45 minute coffee first date, okay, probably not first kiss territory. But a big myth is, oh, you know, it's wrong, weird, or creepy to go for that 1st kiss. And I wanna tell you about my client. I'm gonna call him William. Bill William. I have a client named Bill, And he lives out in the Pacific Northwest. And Bill has had a big, one big sticking point on first dates. By the way, this is a guy who's in his late thirties, and he's had some dating experiences. He's been in some couple of long term relationships and been on plenty of dates. But He came to me because he was stuck. He could not go for that 1st date kiss, or I should say he was struggling on 1st dates. And what he and I discovered or what I discovered was that


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 their dream girlfriends. So book a free strategy. He called 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 artist tricks. He unlocks your most confident self So you can make authentic romantic connections. Your next steps? Book your free call today at dating transformation.comforward/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 dating transformation.comforward/contact Act and transform your love life. Bye.

Part of his problem was he just wasn't going for 1st kisses. Why? He has good reasons for this problem or reasons that make sense in his mind. He used to drink a lot, and Bill no longer drinks. And back in his drinking days, he was on a date or he was at the bars. He got a few cocktails in him, making moves, going for that kiss was not Tough for him. But sometimes he did it when he really didn't have the signals. He made a couple of women feel uncomfortable. And then he said, you know what? I'm gonna get sober, which I 100% believe in.

I'm totally sober. I'm a big sober fan. I had to coach a lot of sober men. So anyway, Bill made a totally understandable correction. He said, I don't wanna be that guy, that handsy, Creepy guy who's macking on girls and doing weird wrong things on first dates. So he started to tell himself a story, an understandable story, but a false one. And that story is creepy and weird and wrong to go for that 1st date. He basically would hug girls good night.

Maybe If he was feeling really bold, he'd go for a kiss on the cheek. But he just told himself, you know what? It's not gentlemanly. It's not right. It's not gentlemanly to make out with a girl or try to. And but that was bothering him because I said, hey, dude. Make out with a cutie. They like it, typically, especially when It's a guy as cool and awesome and successful and just generally awesome as Bill. So I said, actually, you know what, Bill? You're actually it's it's much what's what's more gentlemanly? He thought it was because he thought it was Nice and gentlemanly not to kiss a woman on a 1st date. But then I said, actually, what's nicer and more gentlemanly? To give a girl a 1st date kiss, make her feel attractive and sexy and turned on, or to not kiss her or try to and make her feel like, gosh. Maybe he doesn't like me. Maybe I'm not the kind of woman he wants. Maybe I'm not attractive enough. And so we started to reframe what a first kiss means both to him and to her. And he started to realize, hey. Wait a minute. It's actually kind of jerky of me to not go for a kiss. Maybe some of these women want me to. And then I gave him one of my favorite little catchphrases that I share with many of my clients. I say, the truth is, man, In all my years of dating, and by the way, I've probably been on a 1000 dates in my life, roughly. I have never lost a woman's interest in me by going for a kiss and not getting it, at least as far as I know. I know that I've Lost out on some great wins and romances by wanting to go for that 1st kiss on the 1st date, But letting cowardice stop me, and then I lost some many girls that way. I know because some of them told me. Some of them said, sorry, dude. You had your chance back there. You had a perfect chance to kiss me. You didn't do it. I want a man. He's gonna take some courageous action. So this is all prefaced to 2 very important dates that Bill had. Let's talk about date number 1. Had a 1st date with a really attractive girl named Jill, not her real name. By the way, not Bill's real name. Just be just but I like to use names so you can paint a picture. So Bill had first first date with Jill, Bill and Jill. Bill and Jill went up the hill to have a date, and He pushed out. He went out. He didn't do it. He wanted to go for the 1st kiss, but he didn't. And then we had a good phone coaching session about this after the date. And I was really blunt with them. I said, bro, let me be really honest with you. You might have lost that girl. Think of the romance you just lost out on because You showed her you didn't have the courage to go for it. Think of the connection, the love you might have just lost because you didn't have the courage to go for it. Think of what Your inaction and your timidity cost you. And then I said to him, There is nothing wrong with fear, but there is something very wrong with cowardice. And that really seemed to click with him. Bill used to serve in the armed forces. He was in a branch of the armed services. He's literally been in, like, firefights and and and shot His weapons and and in life or death situations. And I said, hey, man. Nothing wrong with fear. You know what fear is like, But you also know that you can't be a coward. You can't be a coward in the military, your military service, which I know he never was. And I said, you can't be a coward with women. Fear is okay.

Cowardice is not. And that really seemed to reach him, I'm happy to say. And I thought maybe I'd gone too far. I thought, oh, no. Did I just lose a client? Did I just tell him to go f off? And What do you know, Ginger Man, about serving in the military? But he took my note with the good intention that I sent it to him. Fast forward to his 2nd date sorry. A different date with a different woman, and, I'll call this woman, Becky. I'll call her Becky. So 1st date with Becky, just a few nights after his date with Jill, Bill and Becky are in the bar. It's about a 2 hour date and he's doing all the things I teach him. He's flirting. He's teasing a little bit. He's being very authentic, opening up, just being really real, letting her see the real him, Letting his personality come out and having a really good time. He brushed the hair out of her eyes a couple times, and she was, like, touching him back on his knee. So there was some nice reciprocal physical contact back and forth. So then the date's winding down. He says, hey. Let me walk you to your car. And as he's walking Becky to the car, he realizes, oh, man. I can't let another date go by without that first kiss attempt. So he took a deep breath. They got to her car, and he moved in, and he went for the kiss. He just went for it. He didn't even say anything. He just moved in. She kissed him back. They kissed more passionately. Knees and hands started to roam and touch each other in this parking lot at night at a bar in the Pacific Northwest. They had about a 3, 4, 5 minute passionate make out with her leaning up against her car, Becky's car. And it was getting pretty hot and heavy. It's her 1st date by the way. And then Becky says to him, I want you, I want you now. And he said, I do too. I want you now. And then Becky said, Only problem is I have all these boxes and things in my back seat, so we can't do it in my back seat. And then he realized, oh my gosh. She wants to hook up in a car. And then he immediately thought quickly on his feet. He said, well, my car is right over here. Let's just take a walk over to my car.

She said, great. Lead the way. He took her by the hand. They went to his car. His back seat's much bigger than hers, and I don't need to Go further. Let's just say the night ended very well for both of them. They had a, A backseat car hookup. By the way, I told them in our coaching call, I said, bro, I've been doing this for 10 years as a dating coach.


I've been working on my dating life for 18 years. I've never had a first date Car, nookie. I've never had a first date hookup. And, my jaw was on the floor when he told me this story. And I just said to him, well, hey. Look what can happen.

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 1 Amazon best selling book. Dating sucks, but you don't. You're a step by step guide to attracting wonderful women And doing it with total authenticity. Author and dating coach Connell 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 audiobook. Get Dating Sucks, but you don't today. To transform your confidence and Find your dream girl. Look what can happen when you make that 1st date move, when you go for the kiss. Yeah. Like, she basically once once he showed her that he was a guy who could go for that first kiss, then the floodgates opened, And she basically said, I want you. Where is this gonna happen? She made it because she basically almost took more of the lead than he did. But that's what can happen when you make that move. You show a woman, hey, I'm a man. You're a woman. Why wouldn't we have at least a little kiss on a 1st date, if not a hot, sexy make out, and then know, then who knows what can happen by the way. 1st date sex. No, I don't really care whether you have first aid sex or not. Totally fine. If you both want that, it can also go a lot slower. You could wait 3, 4, 5, 10 dates. All good. Totally up to you. Totally up to her. I just wanted to tell you the Bill and Becky story to show you what was possible once you say it's time for courage. It's time to go for that 1st date kiss. So ignore that myth that it's weird and creepy to go for a 1st date kiss. It can lead to some amazing things and it can lead to the quote unquote ride of your life. If you know what I mean. So, yeah, Bill is a new man. Okay. That's myth number 1. I'll Plow through these other 2 myths pretty quickly about 1st dates. 1st date myth number 2 is this idea that you have to score a lot of points to get her into you. You don't have to score a lot of points. You actually really, what you gotta have to do is eliminate mistakes. You know what this reminds me of? I'm a tennis Addict. I love tennis. I've been playing tennis all my life, since I was 12, 13. And I was listening to a great tennis podcast recently, And the pro on the podcast was saying, you know what? Problem with tennis players these days, you know, weekend players, Is that they're trying to hit winners all the time. They're trying to play like Federer, hitting all these winners. But if you just remove your mistakes or at least remove the dumb easy mistakes, You're gonna have a great match. You're probably gonna win because the other person's gonna make more mistakes. And I thought, what a cool analogy to dating. Not that your date is your opponent. I don't mean that part. She's not. She's someone, she's your teammate. She's your collaborator. But On 1st dates, you don't have to score tons of points. What you wanna do is just eliminate mistakes. Don't feel like you have to be the most charismatic, funniest, incredible, wittiest, coolest guy in the history of the world. You don't. You just have to be authentic. You have to be sincere and remove some mistakes. Okay. Remove mistakes like long, awkward pauses. Remove mistakes like interview mode, Remove mistakes like only asking questions and not offering anything. Remove mistakes like, talking about yourself and only you and talking at her and not asking her good questions about herself. Remove mistakes like not flirting. Remove mistakes like not going for a 1st kiss if you feel like there's a reasonable vibe. So just remove those mistakes. I'm reminded of the first date I had with my Then future girlfriend, Lorraine. Now she's my ex-girlfriend. It's been a long time, but she said something amazing on our 1st date, And I still remember it, which is this. She said, guys think that they need to score points with us on dates, but you don't. Actually, you start off with Points? And then, then you lose them, and that's when we lose interest. It's when you lose the points that you begin with. So Stop trying to score points on dates. Just eliminate really easy mistakes. Okay. Let's finish with one more, one more thing. We're gonna do the 3rd myth, first date myth, which is Gosh. There's so many. What's a good one to end on? I would say a really good Final myth that guys get wrong about first dates is feeling like The myth is she won't like me for me. I've gotta be cool. I gotta be cool. And that's actually a big mistake because you don't wanna be cool. You wanna be authentic. You wanna show her the real you. Guys think they need to impress a woman. And again, say the cool lines, or do the most amazing, incredible game. Bottom line is if you stop trying to impress her And instead, try to express your authentic self. You're actually gonna be showing her your best, most attractive self. And, then you're gonna have a really good first date or at least you're gonna have a much better first date than you've been having. Okay. Those are 3 of the many first date myths. Maybe we'll talk about more in a future episode. Until next time. And remember, your future girlfriend, she's out there. She already likes you. She just has to meet the real you. Till next time.

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


Produced by Heart Cast Media.

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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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