How to Get a Girlfriend with Connell Barrett - Struggling to Get Second Dates? Take Drastic Action: “Blow Up” Your Next First Date!

Episode Date: June 5, 2026

Most guys struggle on first dates by playing it too safe. Same dull questions, same dull answers, same text she sends the next day: “I didn’t feel a connection.” In this episode of “How to Get a Girlfriend,” dating coach Connell Barrett shares a drastic, powerful solution. “Blow up” your next first date! Connell breaks down the three rules to take your dates from forgettable to explosively fun. He also explains why the “risky” move is the smartest one you can make. Listen now.NOT GETTING ENOUGH DATES WITH WOMEN YOU’RE INTO? BOOK A FREE CONSULTATION WITH CONNELL: DatingTransformation.comGET A FREE COPY OF CONNELL’S BESTSELLING BOOK, “DATING SUCKS BUT YOU DON’T”: Email: [e-mail] (Write “Free Book” in Subject Line)

And dating, what's safe is risky, and what's risky is safe. Welcome back to the How to Get a Girlfriend podcast. Today, I want to help you get a girlfriend this way. Blow up your next date. Blow it the fuck up. Blow up your date. If you're tired of dates that don't go anywhere, change it up, blow it up. Here's what I mean.

So long before I became a dating coach. I was a lot like you, just an introverted dude, nice, smart, but not naturally confident. And I played it safe. And I was getting kind of fatigued on first dates that mostly didn't go anywhere, mostly back in the day from me, before I figured out and kind of cracked the code on this whole how to approach and attract and connect with women thing. And so long before I was a dating coach, I was on a first date with a girl named Natalia. I met her on Match. And at the time, I was so fatigued of dating.

You know, I wasn't just tired of struggling, but I was also getting kind of bored. I wasn't even enjoying dates. There was a lot of, you know, all the small talk, where are you from? What do you do? How many siblings do you have? all those questions that can, you know, really drag you down and make a date feel like a chore. And I remember I just said, I'm going to do something different tonight. I want to try something very different. So she and I sit down at some Irish pub in Midtown Manhattan, and I say, I have an

idea. Let's play a game. And she said, what do you mean? And I said, well, neither of us, here's the game, neither of us can ask a single question on this date that we've ever asked on a date before. And she was like, that sounds great. I'm all in. We high fived. It's like, cool, great. And so I said, you go first. Ask me anything. And she said, when was the last time you cried and I told her the truth at the end of my cousin Vinnie. This is not a joke. It sounds like a schick, but I'm serious. So at the end of my cousin Vinny, whenever I watch the end of my cousin Vinny and he finally gets Ralph Machio off of those bogus charges and Joe Pesci and my future wife, Marissa Tome, win the case. It just, I don't know, it got to me a couple

times. So I said, oh, I cried at my cousin Vinnie. And she said, oh, my God, you're so lame, which she's not wrong. And then we just gave each other all these fun, rapid fire. Anything goes questions. I remember I said, okay, if you could punch anybody in the face, who would it be? And she said, she kind of surprised me with her answer. She said, Ted Mosby, the name of the main character on how I met your mother, Ted. And then she explained why she hated Ted Mosby, just that he's a character who sucks. And so this went on for a while. Back and forth, rapid fire questions, all bets were off.

It's like, what is your greatest fear? And I told her, whatever it was. I forget, it's been many years. And I asked her, and I'm a journalist, or I was a professional journalist at the time. So I'm pretty good at asking questions and asking surprising questions. So I was really, this was just a way for me to lean into my strengths of being a good interviewer, a good conversationalist, I like to think. And then things got actually pretty real. About halfway through the date, she said, have you ever cheated on anybody?

Have you ever cheated on a partner? And I was like, oh, shit, this is really getting real. Do I tell her the truth? And the truth was that, yeah, I had cheated on a woman earlier, years earlier. Felt terrible about it, but it was the truth. And so I said, yeah, I had. And I really owned it, too. I remember thinking, yeah, I have.

And her reaction was really interesting. I had never told a woman that before. Certainly not on the first date. I don't recommend you try this at home necessarily. This is a this worked for Connell move. Your mileage may vary. But I remember her reaction was really interesting. Emotionally, she pulled back, but physically she leaned forward.

It was like there was a vibe of, damn, this guy's actually telling me the truth. Combined with, but can I trust him? She was almost excited, almost, for lack of a better term. It was almost like, whoa, finally a guy who was just telling me the truth. and I told the story of the woman I cheated on and how it happened and why. I didn't go into it for 10 minutes, but, you know, had to tell her a little bit about it. And I think it actually kind of created trust with her because she realized, wow, if he's going to tell me that, he's not giving me some line of bullshit saying what I want to hear.

And I just felt really free that night. I felt really freeing to let go of all the things I felt like I had to say, had to had to do and just be really spontaneous and in the moment. We kiss good night, Natalia and I, and I remember she texted me. I remember she texted me, quote, I have this floaty feeling I could get used to this. Winky emojis. Pretty damn good text message to get back from a woman. And before that date with Natalia, I was in.

a little bit of a slump, not getting second dates with most of the women I was meeting. And I remember thinking, wow, this is pretty cool. I didn't use the term blow it up at the time. I just made up the term blow it up recently because I thought, hey, what would be a cool, different kind of insight to share with my audience here? And the insight is give women something they're not used to. Break that pattern. Zag. Every other guy is zigging. You can zag. blow up your next date. Here's how to do it. Here are three rules you can follow.

Your mileage may vary, but you can certainly give it a try. Three rules to follow to blow up your next first date. Rule number one, no questions you've ever asked on another date are allowed. And you can even say that. I've got an idea. Let's shake up our date. You don't need to say blow it up, but you can say, I have a fun idea. Let's do something different for our.

date. Let's ask each other any question as long as it's nothing we've ever asked before on a date. I think a lot of women will really like that. Rule number two for blowing up your next date, no lying. No lying. You both have to wear Wonder Woman's Lasso of Truth. I remember with Natalia, I mimicked having a lasso, and I threw it around her. I'm like, okay, remember, we're both wearing the lasso of truth. And I was wearing a two. And I really basically acted like I was on truth serum. And I used to be such a liar. Now, liar's not the right word. Such a, say what makes her like me kind of guy on previous dates. What does she want to hear? What will attract her? What is good content? We didn't say content back then. What is good game?

And it felt so freeing to just say, you know what, let's just tell the truth. Drop the guard, unguarded. This is me, warts and all. Love it or hate it. And that felt really good, really good. So rule number one, no questions allowed you've ever asked before on a first date. Rule number two, no lying. You both must wear the Wonder Woman lasso of truth.

And rule number three, no trying to give a good answer. Don't think through the lens of, is this good? Is this attractive? Think through the lens of, of I'm expressing the truth. Think express the truth, not impress the girl. Express the truth, not impress the girl. Paradoxically, what I've learned from my 21 years in this world of looking at dating and studying it, 14 years as a coach, is that when you stop trying to impress her and you fully express, you actually start getting the kind of attraction and romantic sparks

you want. So you actually do impress her in a way by not trying to impress her. One of those brain melting things I learned along the way that I impart to my clients. Speaking to my clients, here's a quick commercial paid for by me. If you would like to talk with me about how my dating coaching works, if you want to blow up your next date or blow up your whole dating life and start again and get a great girlfriend, then you can do that by talking to me. I am a dating coach. I do one-on-one personalized coaching with men. I can coach men anywhere in the world. And my specialty, if I had to say, I have two specialties. It would be helping men with approaching, knowing what to say and how to approach women in a very confident way. And also just the act and art flirting,

how to flirt, how to make sparks, romantic sparks happen. So that. You never run out of things to say, flirting really well, having really good dates. So if you're interested in learning how my coaching works, go to datingtransformation.com. And you can book a free call with me today. Or at least you can book it today. We won't have it for a little while. A few days anyway. Not everybody wants coaching.

That's totally cool. If you don't want coaching, then I would love to give you something just because you're a person listening to my podcast. And that really means a lot to me. It really does. I'm a huge podcast guy. And I have such a strong bond with my face. favorite podcasts. I love the rest is history. I love Screw it. We're just going to talk about the Beatles. I love the rewatchables. The Ringer podcasts are awesome. And I have such a strong

connection with the people on my favorite podcasts. And if you like this podcast and want an even stronger connection to me, then I want to send you my book. I wrote a book came out five years ago called Dating Sucks, but you don't. Did pretty well. Hit a couple bestseller lists, and I want to send it to you for free. So if you want a free copy of my book, email me, Connell at datingtransformation.com. Just put free book in the subject. I will see your email soon, and I'll send you a PDF of my book.

You can instantly get it and start reading it. So email Connell at datingtransformation.com to get that. All right, back to blowing up dates. Here's a story. When I started blowing up my dates, I knew I was on to something. And I said, all right, I want to make sure I give every woman on every first date the full Connell experience going full Connell. And I remember I had a first date with a woman I was really excited about. And if you're anything like I used to be, when you're really excited about a woman,

in a way it kind of gets you in your head and can make you play it safe and can make you play a prevent defense. And they say in the NFL, if you play the prevent defense, they call it. the prevent defense because it prevents you from winning. And I remember I had a first date lined up with this really beautiful woman, an actress from Eastern Europe. I forget her name. I wish I could remember it.

But I'll call her Lena, beautiful, slender brunette, just dynamite, gorgeous actress. I met her at a Tony Robbins event. So we had a lot in common. We met at this Tony Robbins event. I approached her. We chatted. I got her number. And it turns out she lives in New York and we went on a first date. And I remember going into the date thinking to myself, don't play it safe. Play it risky. Because what does every guy do with this beautiful woman, actress, dynamite? Look, every guy, not every guy, dozens of guys at the Tony Robbins event.

we're talking about this woman. She was one of those women who were like, oh, yeah, did you see that girl? Oh, my God. She was even on stage with Tony at one point. So she got everybody's attention. Anyway, so I was excited to have a first date with her. I was also nervous because I was like, damn, how's it going to go? She going to like me.

Wouldn't it be amazing if we hooked up or if we dated? And those kinds of thoughts about the outcome can actually create a block so that makes it harder for you to get the outcome because it makes you play it safe. And there's a really cool paradox that one of my coaches taught me back in the day. He used to say to me, Connell, in dating, what's safe is risky, and what's risky is safe. I thought that was kind of a cool little mind-blower. What did he mean by that? Well, what he meant was, and I tell my clients the same thing, that what you think is risky, Like making a move, telling a woman she's sexy, doing a bold approach. It feels risky to you because you're pushing your comfort zone, but it's actually a very safe,

smart dating move to make because women like boldness, women like a man who goes for it. At the same time, what feels safe, hanging back, being mysterious, not letting her know if you like her, or other cautiousness walking on eggshells, so to speak. That might feel safe in the moment because you're not stretching your comfort zone, but it's very risky because you risk a woman feeling like you're just not a guy who goes for it. And generally speaking, a quality, beautiful, attractive woman wants a guy who knows when and how to take risks. So risky is safe and what's safe is risky. And I had that mindset as I walk into the Tempest bar in Chelsea.

No longer there. Chelsea's there. Tempest is not. And I walk into this really cool, fun dive bar for my first date with Lena. And I'm thinking, all right, play it risky. Don't force it, but play it risky because risky is safe. Safe is risky. And this is a variation of blowing up the date.

This is part of the theme here. By the way, do not try this at home what I'm about to say to you. Do not say this to a woman, but know that it's what I said. So I get to the bar and I'm waiting for Lena and I sit down in this area of the bar, sectioned off kind of a dark, quiet area. Seats about 15 people and it's just me and maybe one other person. However, before Alina arrives, a whole cross team of dudes shows up. I think it was a lacrosse team. They had just finished a practice near. and they're all having post-practice drinks at Tempest, fun little grungy dive bar in Chelsea. And all of these beefy shorts wearing sweaty, 20-something lacrosse dudes enter this area and sit

all around me and near me. So eight or ten guys, quite the visual. They're there for a few minutes. And then Lena arrives for our date. and I stand up to greet her, give her a little hug. She sees where I am. I'm surrounded by all of these sweaty men in this small room, and she looks at me and smiles and sort of is assessing the situation.

And I said to her, oh, yeah, I thought you might want to have a gang bang. I don't know where that came from. It was just a spontaneous thing. I read the situation, and I thought, you know, what, I'm just going to say the first thing that comes into my mind. And it wasn't planned. I wasn't scripting that. It just came out of the moment. I saw her looking at all these guys. And I thought, well, let me just say the thing. And she laughed so loud. She thought it was hilarious. And it was a great icebreaker. Again, I cannot state

this enough. Do not make a gang-bang joke at the start of your first date. Not for every guy. But in a weird way, somehow it was the right thing to say to Lena. Maybe I did some computation in my head. I could tell from the Tony Robbins event that she was a free spirit. She had a good sense of humor. We did talk for 10 or 15 minutes there. And I could get a sense for her how she was on stage. Definitely a fun person with a good sense of humor. I would. would not say that as a go-to move at all. But anyway, that was my gang-bang joke that I made with Lena, and it helped the date kick off in a really fun way. And it actually went pretty well, went pretty well. And it was a good, it was a small example, not a small example, but a micro-context

specific example of me blowing up the date. I wanted her to know, on some level, I knew that I wanted her to know that I'm not like other guys. I'm not going to sit here and interview you and ask you how your day was, at least not for too long. Play it safe. I'll make the raw joke. I'll make the gang bang joke. I'll go for it. And the other thing I remember, we went to a second location. And she straight up asked me, she wasn't quite clear if this was a date or not. I'd think she just wasn't sure. And I said, hell yeah, this is a date. I don't bring my lacrosse buddies out to meet just anybody. But yeah, this is a date. So I didn't play it cool. I didn't play it safe. I didn't hold cards back. I let her know that I really liked her. Or I was starting to like her.

And we ended up at my place. We watched, we actually watched a movie she was in, in whatever, or the Eastern European cinema, some European movie. And it was, it was really funny. She said, hey, do you have Netflix? And we've called up her movie on Netflix. She's like, oh, I want to watch this scene. All of a sudden, I'm watching a beautiful half-naked woman in her lingerie on the movie screen. And I look at the movie, and I look to my right on my couch.

And I'm like, that's you. It was really fun. And it was a really good date. And I can't, I don't remember what else I blew up. about that date, but I just remember that moment. So, this idea of blowing up a date, it doesn't mean every single moment of every date has to be wild and weird and crazy. You just want to give her an experience that she hasn't had before.

And there's a paradox here, maybe, is that the right word, or dichotomy? You want to blow up the date by being a very relatable, authentic version of you, which is just being you, but giving her the fun, the pattern, the variety, pattern break, a variety of a very different date. So when I say blow up the date, I am not saying be different, be somebody or not, say weird, weird, crazy, not normal stuff. Absolutely not. Be even more you. That gang bang joke, that is my sense of humor. At least it was that night in that moment. And I have a pretty raunchy sense of humor. I'll make a raunchy raw joke.

And I'm not going to hide that. That's the kind of joke I might make with my personal trainer when we're just shooting the shit at the gym. But I'll do it on a date. I'm not afraid to go to that place. Now, not every woman likes that. I have plenty of stories of me failing. Maybe that's a whole separate episode.

I want some. Let me just be really honest with you. I once blew up a date and it actually blew up in a bad way. I had a date where I thought, I'm just going to be totally real and honest with this woman. And we started talking about the first, we started talking about our youth and early sexual discoveries. And somehow, some way the topic got onto masturbation.

And I told her about the first time I touched. myself. And I didn't do it in a vulgar way. It happened somewhat organically, I think, my memory. And I talked about it a couple times on other dates. And a couple women really liked the vulnerability talking about, oh, the first time I discovered my body. And it was a really honest open conversation. And it blew up with this other woman. She said, why are you talking about this? I don't want to talk about this. And that's fair. That's fair. So I will not lie to you, dear listener. When you blow up a date, you risk blowing up the date. But you also give yourself a really good chance of a strong, making a strong, amazing impact on that woman and making you

memorable in a good way and making her want to see you again. That's what I'm getting at here. So I'm not going to bullshit you and pretend like this is an instant quick fix. It'll make every woman want a second date with you. The idea here is that it makes you more polarizing. at least, or maybe polarizing is too strong over the word. It makes you more impactful for a woman who really likes your type. But yeah, don't talk about masturbation. I'm not saying that. And don't make gang bang jokes.

I'm just giving you extreme examples of blowing up the date. You can blow up the date this way. It can be this simple. Here's a great example. This is my third date with my girlfriend, Jess. Now, my girlfriend, Jess. Very simple. I said, hey, I have an idea.

Let's do a reverse date. We were planning date number three. I was so into her. I still am years later. I was so into her and really liking her. And I'm like, okay, I want to do something fun and different for our third date. Kind of surprising. And I said, let's do dessert first.

Let's do a dessert first date. We'll start off getting cheesecake at this fancy cool cheese cake place. And then we'll go to this cool restaurant. So it can be that simple. That's a little baby blowup of a date. Just doing something, a little twist on what people are used to. So it can be as simple as that. Dessert first is a blowup date.

Another example of a blowup date, this is really great, especially now that summer's here. If you can find a way to do this, I called it a devious date at the time. I remember telling friends, I had a devious date. A devious date is when you and she do something a little bit naughty. I don't mean sexually. I mean, you do something take down.

that's a little bit naughty. I dated a woman from Match.com back, man, this was probably 15 plus years ago. We had a date. I think it was our second date. Our first date was karaoke, which is very basic, not a blowup date. But then I thought, all right, what can we do? That's different for the second date. And it was a heat wave.

It was like July or August. And so I said, I have an idea. I know this hotel. And I think I know how we can sneak in and use the hotel pool, which is only for the guests, but we can sneak in because, you know, I know the property. Somehow I knew. It was a hotel where the pool was on the ground level. So if you could just get in the hotel and walk into the pool area, while somebody else opened the door, since I don't have a key card, you can get into the pool. And you're not officially supposed to use. You know, use the pool unless you're at the hotel, but we snuck in. And so it was really fun. It was like the two of us were collaborating. It had a swim up bar, which was really cool. You just swim up, you order a drink. It was so fun. And that was like a devious, devious thing to do together. By devious, I just mean, you know, I don't mean, don't go shoplifting together. Don't commit any actual crimes,

please. But it's okay to break a rule. don't dine and ditch. I do not sign off on that. But sneak into a pool or if there's some kind of sneaky thing that the two of you can do together, that creates a really fun connection. It's like the two of you against the world. So those would be some ways to blow up the date. So anyway, go think about at least one or two ways you can blow up the date. And the simplest thing to do is just what I mentioned earlier. On your next first date, say, hey, I have an idea. idea. One rule for tonight's date. Tell me if you're in. No questions allowed that we've asked on previous dates. We can only ask each other new different questions, totally random. Ask me anything.

That alone will make your next date stand out and give you a really great chance for a second date. All right. Thanks for listening. Until next time.