How to Get a Girlfriend with Connell Barrett - “The Best First Date of My Life” — How Tony Learned to Flirt and Won Jennifer Over

Episode Date: June 26, 2026

If you’ve ever wondered, “What do I say? How do I flirt?” Tony’s story will resonate. In this episode of “How to Get a Girlfriend,” dating coach Connell Barrett talks with Tony, a divorced dad and software engineer who had some flirting breakthroughs that helped him win over Jennifer. If Tony can go from struggling to talk to women to finding his dream relationship, so can you!NOT SURE HOW TO FLIRT ON DATES? 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 so I was scared to death when I first entered the dating game again. And I had no idea what women were expecting of me or what or how to flirt. Welcome back to the How to Get a Girlfriend podcast. I am your host, dating coach and bestselling author, Connell Barrett. I help nice guys, good guys, solid guys go from struggling with dating to getting really wonderful, amazing girlfriends. And to that point, I have a really special guest here today. My client, Tony, is joining us.

And Tony is an amazing man. He's a software expert, computer expert, mid-50s, early 50s. And Tony is joining us today because he recently found a wonderful woman to be sharing his life with after overcoming some flirting and dating challenges. And Tony is here to talk about some of the best things he learned and help you have the same kinds of results that Tony has had. Tony, thanks for being on the How to Get a Girlfriend podcast. Yeah, thanks for having me. Yeah, great to have you here. Let's start with where you were when we first talked. Like before we started working together, I know you had some challenges.

You had mentioned to me, oh, I get stuck in the friend zone, I'm not sure how to flirt, maybe just feeling a little bit lonely at times. Where were you in your dating life when we first started working together? What were some of your struggles? Yeah, so I think a, I had a lot of confidence issues, and I think because of that, I made some really bad decisions kind of in my dating life and settled for women that that weren't a real good match for me or that I wasn't really into and just was not happy. I was not having a good time. I think a lot of it had to do with the fact that I didn't have a lot of dating experience before I got married and I was married for a very long time.

I got out of a very 17-year marriage and didn't really know how to do it. And so I was scared to death when I first entered the dating game again. And I had no idea what women were expecting of me or what or how. to flirt. I didn't even know it. Like, I would hear that word. I didn't even know what that meant. It was like, and it seemed like everyone around me knew, and I didn't know. So, yeah, those were, and then even just feeling like I was the type of guy that women would want to date was a big problem. And, yeah, so those are some of the big struggles I had. What, that, that voice of self-doubt that we talked about way back when we first spoke. What did that voice say to you

to say, hey, women won't want you because of X or Y? Yeah, I think, well, at the time, I was, I was fairly overweight, and so I had a lot of image issues. Now, you know, I've, I've, I've, you know, done some work in that area, and I, you know, I feel a lot better about my body there. but definitely that was a that was something that was a concern. I think also I'm a single dad and didn't know how many women would be into that. I also felt like because I didn't have a lot of dating experience that just women weren't going to be interested in me

when they would talk to me, right? Right. Because women in your mind, women, oh, they want a more experienced guy. They want a guy with more history with dating women, more charismatic, that kind of thing. Exactly. Like the Fonz or something.

The guy who knows how to treat a woman And, and, and, and, and, and, and, and, and you need to be able to hit the jukebox and make the jukebox come on just with magic like the font. Exactly. Right. So, um, I think, oh, sorry, go ahead. Yeah, I think just missing that, um, there was, I felt like there was something that I just didn't, I didn't have or, or that, that women wanted that I didn't even know about. And, and, and it was, um, or, or certain, or I just didn't know, know, know the right thing. to do and it just made me very nervous when I talked to women. And so usually those conversations

didn't go well. Yeah. Yeah, the nerves about talking to women typically come from two sources of internal doubt. One is, I don't know what to say. I don't know how to flirt. But the deeper feeling is, well, why would she even want to talk to me or be with me anyway? Because I'm whatever. I'm shy. I'm a nerd. I'm not experienced. So that's super common. By the way, I think it's ironic that you thought you had to be Fonzie, and I look a little bit like Richie Cunningham. It was meant to be maybe. I have a Richie Cunningham vibe. So when we started to work together, were there any insights or aha moments you had about yourself where you got to look at yourself and say, hey, wait a minute, I'm a successful software expert.

I am a musician. I have all these things to offer. What helped you start to at least begin to flip the issue to feel more confidence in you? Yeah, I think when we did that exercise where we kind of listed all of, like tried to make the case for why women aren't into me. And I had to prove that. And it was very clear to me. I'm a very logical person. I'm a software engineer and I think about things in a very, very logical way.

Like, you need to have data to prove why a certain thing is true, right? It's not just true because you feel it. And I, and so I think when we went through that exercise and I just realized there wasn't, there wasn't the data to really support these beliefs that I had around why women didn't want me. um uh like like even when like for example even when when when i was um you know a bit heavier than i was now than i am now i was you know i was in a relationship with a woman and she actually told me that she thought i was attractive right and and but still i had this narrative in my head that was that was saying you're not attractive to women right and um and so yeah it was

things like that that that help me um i mean it's i can't say it's something that is gone completely right i have to actively um remind myself hey you are you are attractive you are um you are you do have something to offer like you said right right and um but but it definitely helped me help help help give me a um i think sometimes when you when you when you're able to name something it all of a sudden it becomes something that's like you're able to overcome it, right? Right. And I feel that that's kind of what we did was we kind of, where you helped me do was really like actually call the thing for what it really was. And then I could, I could find a way to get to overcome it.

Yeah. So you and I did an exercise. I call it the awesome list. 25 reasons why, minimum, 25 reasons why you're an awesome choice for women. And if you remember anything from the list, what are a couple of things from your list that when you think about them and make you puff out your chest a bit and say, yeah, that's pretty damn awesome. That sounds like a good catch. Do you remember? Yeah, like, I think, like, I'm an amateur singer-songwriter.

And I think, you know, a lot of women would like, a guy who can serenade her, right? Yeah. It's certainly the case for my current girlfriend. So she loves that about me. And there are other things like I have a lot of exciting, like I'm a very active person and I have a lot of exciting hobbies. Like I love to go skiing and I love to be outdoors. I even love hiking.

Connell, I know you're not a hiking fan. Hiking should be illegal. That's all I'm saying. And then I love sailing and I even got my sailing certification. And so I think those are things that a woman might be interested in or definitely would be interested in. Or even would like to share with me. You made a great insight a minute ago where you said, I'm a logical guy.

I like data. And that can hurt us in flirting because logical information is not really where we live with flirting. Flirting is a bit more playful, emotional, which we'll talk about. But the nice thing about an analytical man like your good self is once you look at the raw evidence that you are, quote, not what women want, and you realize this case would be thrown out by the jury, sorry, reasonable doubt. It wouldn't get to the jury.

The judge would be like, get this shit out of here. There's no evidence of it, or at least not evidence that every woman's not going to be into you. And you obviously got a lot of a wonderful woman in your life to prove that old belief false. But okay, we got confidence, which is really important. Women want a man who has confidence in himself. You started to begin to see that. But also women want a guy who can flirt a little bit or who can just have nice, enjoyable conversations. I think if you would about, it could be your first messages or your first date with your now girlfriend, Jennifer, or anybody else you met along the way.

What flirting or how to talk to women advice can you share with our listener, things that I hopefully helped you get better at? Yeah, I think, you know, at one point we talked about values, right? And one of the values that was really salient for me was playfulness. And that's something I really, that's actually one of the reasons I really liked your opener, which is what I used with my, with my now girlfriend of the time traveler. The dating app opener. That's right. And so.

May I read it? Let me read it. Yeah, go for it. Not literally yours, but here's what I say. Yeah. So I call this the time travel opener or the back to the future opener. So I'm watching Back to the Future a few months ago. And I'm like, you know, it would be fun to try.

And so I just started experimenting with this. I sent this to a woman named Gia on Bumble. Gia, I'm writing you from the future. The year 2031, we're madly in love, but we just had a big fight. Can I ask present day you something? Our love depends on it. Gia writes me, hey, Connell from 2031, I've been expecting you. Ask away. It's a little red heart. Hey, Gia. Well, future us fought over our very first date. I said that we met at a cozy wine bar.

You said we had gelato. Which one was it? Future soulmate, wine bar, or gelato? And then she says, Connell from 231, how could you forget? We met at a wine bar. And so then the first date closes, I said, okay, well, we better meet up at that wine bar so we can make sure our future love happens. What night are you free? So basically, that's the time travel or opener or variation of that. And so that's a fun, playful way to break the ice with a woman on a dating app. Tell us how Jennifer responded to that or how you felt about using that. Yeah.

So I modified it a little bit because it just from her profile, it seemed like she, She was more of a boba person. So I said, hey. So I said, hey, yeah, did we get ice cream or boba? And she actually responded, but actually you can get them both at the same time. It's called a boba float. And so, and I'm like, oh my gosh, how could I, that's like, how could we have forgotten? We were fighting about nothing the whole time.

Anyway, it was just like, and then we had this really bantery conversation about that. And I think the thing I really like about that opener, and it also worked very similarly with other women on the dating house was it just sets the conversation up to be very playful from the very beginning. So you're like, like just did the premise of the, of the, of the, uh, what you're asking her is, is very playful and it lets her be playful. You know, like, like my, my, my, my, my, my, my, my, my, my, my, my, my girlfriend was with me on, on the app. And then, and then, you know, I can, we can have a nice banter around that thing. And, and, um, uh, so I actually used it a lot because I, I, I, I really liked that aspect of it.

So much better than just asking someone how their day is going. Right. And then that's so boring. And she told me later, like she showed me her hinge afterward that she had hundreds of messages from guys, like that she hadn't even like read. They were all unread. but she read mine and it stood out because it was just so different. And that's what she said.

It was because of because of that opener that she actually responded to me because most guys are just saying like, hey, gorgeous or things like that. Yeah. What are you up to? How was your weekend? Right. I'm so glad to hear that, not just because of how you and she ended up together. but the back to the future opener it's not about the back to the future gimmick although that's fun i think

it's about hey let's play let's have fun here yeah and flirting in a word is about play it's not sexual conversation necessarily it's certainly not dry informational logical conversation it's let's play that's essentially flirting is literally defined i believe in webster's as playing at love it's and playful. So the opener is playful. Women love that. It sends a great message that they're going to have fun with you on a date. Maybe you'll fall in love. Maybe you won't. But what keeps a lot of women from having dates with a guy is just like, I don't want to be bored. I don't want another boring, logical conversation. So he sent a great message to Jennifer that way. Can you tell us about your first date? I know when you and I first spoke, you had mentioned, oh, I get stuck in

the friend zone or I don't know how to flirt with women. On your first date with Jennifer, what did you do differently than you had been doing before? What helped it to go well? Any first date tips? Yeah, I think the biggest thing that helped me, or I don't know if it wasn't something I did consciously, but it was something just I realized after the fact, was that I was not, I was very, I was relaxed and having fun on the date. Whereas like previous dates,

I'd be very nervous about whether or not she likes me. It's like, for something that was very, very important. It was like, like, she needs to like me. It's very,

very important. And so, like, and so I found myself saying things that weren't me because I thought that's what she wanted to hear so that she would like me. And, um,

and, uh, I had a different, a completely different experience with this date was that I I mean when I first saw her I mean she was beautiful and I was very attracted to her and I definitely really wanted it to work out but I didn't have this sense of panic that it wasn't and that that this that my future happiness depended on her liking me right and so that that really allowed me to be just

stay in the moment and, and, and then have a conversation with her as myself. And it turns out she really likes the real Sean, which is, which is great. So I think that was one thing for me that just made the date so much more fun. Hey, Tony. I'll pause there. Okay. You back up and say, turns out she really likes the real Tony, because you said your name. Oh, okay. So it turns out...

Three, two, one, go. It turns out she likes the real Tony. So I think that was something that made the date very fun for me. Didn't you tell me that you were her first, first date in a long time? Yeah, I was her first date in... First, first date in 13 years. Wow. Yeah.

Think about the impression you had to make on her. You're bringing to her romantic table to make her go, okay, I'll actually meet this guy, even though it's been 13 years. That's incredible. I know. The interesting thing is I don't even think she thought it was a date. She just, she wanted, she had tickets to this concert that she wanted to take someone who would appreciate it. And since she knew I was a musician and and and, uh, because I had a picture of me playing guitar

on my profile, um, she invited me to this just to share it with or just so that the ticket didn't, wouldn't get wasted. Uh, um, but I certainly thought it was a date. Um, and we just connected and, um, and had a great time. And it ended with a, um, steamy first kiss. So, yeah, it was wonderful. What was the best moment from the first date? Or was there a do or die moment? Not do or die, but was there a moment of truth where you're like, oh, gosh, I really should kiss her and you just went for it? Or you said something flirtatious, you just went there. What was the highlight moment that you think was like your favorite memory from that first date? I think for me it was, so we were sitting.

So first off, it was like the most romantic location for a first date. We were like sitting on the beach listening to this piano concert. And so, but we were all wearing headphones, and that's how everyone was here. So you could go anywhere on the beach and still listen to the concert. And the guy, the artist encouraged us to do that. So, like, halfway through the concert, I said, hey, let's go for a walk. And she said, yeah, that sounds great. So we went for a walk.

And then I reached down and took her hand. And, like, I think for me, that was the first time I, I, with her, that I, I, I don't know, made a very explicit, gesture that I was, that I, that I, that I, that I, that I really, um, really was into her. And, um, she, like, she accepted, like, took my hand back and we walked with our fingers entwined on the beach. And I think that, that moment definitely took some courage to do that. Because like, wait, what if she, you know, she, what, you know, we just met. What if she doesn't want, you know, to do that. So. And then it was like, from that point on. on like we walked along the beach and then we walked up to the, the, get closer to the, to the person who was playing piano and just standing there listening to the music.

And she just kind of leaned her head on my shoulder. So I put my arm around her. And we just kind of listened. And it was, and I, from that moment on, I knew that, well, I knew that I was going to like go. for the kiss at the end of the night. Because it was very clear that, like, she was giving me very clear signals that we were, that she was enjoying my, my, my, my, my, my,

my touch and my, you know, being close to me. So. Amazing. That's a great tip. If you, if you live near a coast, go on a beach date. Women love beaches. I just took a new online dating photo of me for my profile of me on the beach and it's just, Women are like, oh, yeah, I bet.

And that's another thing we did is, you know, as you know, I'm a big authenticity guy. It's all about let's have the most authentic, attractive version of a guy. And for you, we're like, okay, Tony likes the boat. Tony likes to play guitar. So we have photos on your profile of you authentically doing things that you're into, right? Right, yeah. It was, yeah, we had those photos. that show that part of me.

Yeah. It's like let's market ourselves, but in a genuine real way, like, hey, this is the real me. And that's why I'm such a big fan of authenticity. And clearly, Jennifer likes the most authentically awesome Tony. So how do you feel now about your relationship, but also just about yourself? Like compared to where you were before versus now, how do you feel about Tony as a man? And how do you feel just being in this relationship with Jennifer? Yeah, it's weird. It's like I can't even remember what that old Tony was what it was like to be him, you know?

It's like, you know, we've been dating for like two months now and and it's been so much fun. And just it's made me me so happy. And it, it's, and it's, and it's, I am, I feel in the past, even, even in my marriage, I don't think I was, um, I think I was always settling for, for, for, for, for less than I deserve. Not like in a pretentious way, but like, but things that, but things that weren't good for me, I guess is the right way to say it. And, and, but with Jennifer, I feel, I don't know, I feel like I'm not settling for anything. and we connect on so many different levels. We share a passion for cooking and food,

and so we connect on that. We both love our kids and we connect about that. And it's something that we share, and it's something that we appreciate about each other. And we just have so much fun together. And it's been so, it's, it's been so incredible. And I almost don't, I can't, you know, can't, I pinch myself. Because it's been so long, right?

It's been so many years since I felt that. And it just doesn't seem real, but it is. Incredible. You're a lucky guy. Don't forget, though, she's a lucky woman. You're both lucky to have found each other to incredible people. For the guy listening to this, if he sees himself in you, a guy who's maybe a bit introverted, a little bit more logical and isn't naturally extroverted, if he doubts himself or just doesn't know how to flirt, what final piece of dating advice would you give a guy listening to this to, take a step in the right direction.

Yeah, I would say that there are, as, as, as, as, as, as, as, as, as, as, as, as, as, as, as, as, as, as, seeing the movie Notting Hill, right? And there's that scene where he says, where he's talking, he's talking to his two friends that are happily married. And he says, you know, you don't understand how lucky.

I can't remember exactly what he said. It was like, you don't understand how lucky both of you are. I mean, to find someone you love that loves you, the chances are just so minuscule, right? just so impossible. But like I disagree. I disagree with him. What was the name?

The character. Hugh Grant. Anyway, I disagree with that. I think, I think we, it's, it is,

it is, it is, it is possible to find that. Um, um, um, um, for,

for yourself. Incredible. Well, thanks so much for being your show. Uh, back off. Thanks so much for being here, Tony. You have given us so much hope and insight. And as I say, at the end of every podcast episode, your dream girlfriend is out there, but she's going to have to meet the real authentic you. And Jennifer certainly met the real best authentic, Tony. Thanks for being here today.

Of course. Thanks, Connell. And by the way, if you would like to get your dream girlfriend, if you would like to find your Jennifer, or if you just want to get some dates, and feel a lot more confident and learn how to flirt with women, then you can certainly do that by going to my website, datingtransformation.com, and you can book a free call with me to have a consultation to find out if one-on-one dating coaching might be something you're into. And if you're not into that, no worries. Keep listening to the podcast every week I'm here to try to help you flirt better, find love, and just find that self-confidence and from a real authentic place. So thank you very much for listening. And until next time. Thank you.