How a Shy, Lonely Software Engineer Learned to Flirt and Found his Dream Woman—and How You Can, Too!

Speaker 1 felt like there was something that I just didn't, I didn't have or that

Speaker 1 women wanted, I didn't even know about. And it just made me very nervous when I talked to women.
And so usually those conversations didn't go well.

Speaker 2 Welcome back to the How to Get a Girlfriend podcast. I am your host, dating coach, and best-selling author, Connell Barrett.

Speaker 2 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.

Speaker 2 My client, Tony, is joining us. And Tony is an amazing man.
He's a software expert, computer expert, mid-50s, early 50s.

Speaker 2 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.

Speaker 2 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.

Speaker 1 Yeah, thanks for having me.

Speaker 2 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.

Speaker 2 You had mentioned to me, oh, I get stuck in a friend zone. I'm not sure how to flirt.

Speaker 2 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?

Speaker 1 Yeah, so I think

Speaker 2 I

Speaker 1 had a lot of confidence issues. And

Speaker 1 I think because of that, I made some really bad decisions.

Speaker 1 kind of in my dating life and and and and settled for women that that weren't a real good match for me or that I wasn't really into and

Speaker 1 just was not happy. I was not having a good time.

Speaker 1 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.

Speaker 1 I got out of a very like 17-year marriage and didn't really know how to do it. And so I was scared to death when I first entered

Speaker 1 the dating game again.

Speaker 1 And

Speaker 1 I had no idea what women were expecting of me or what or how to flirt. I didn't even know what, like, I would hear that word.
I didn't even know what that meant. It was like,

Speaker 1 and it seemed like everyone around me knew and I didn't know. So,

Speaker 1 yeah, those were, and then even just feeling like I was the type of guy that women would want to

Speaker 1 date was a big problem.

Speaker 1 And

Speaker 1 yeah, so those are some of the big struggles I had.

Speaker 2 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?

Speaker 1 Yeah, I think,

Speaker 2 well,

Speaker 1 at the time,

Speaker 1 I was

Speaker 1 fairly overweight. And so I had a lot of image issues.
Now, you know, I've, I've, you know, done some work in that area, and I've, you know, I feel a lot better about, about, about my body there, but

Speaker 1 definitely that was a, that was something that was a concern. I think also, um,

Speaker 2 I'm a,

Speaker 1 I'm a, I'm a single dad and uh didn't didn't know how many women would be into that.

Speaker 2 Um,

Speaker 1 I also felt like um

Speaker 1 because I I didn't have a lot of dating experience,

Speaker 1 that

Speaker 1 just women weren't going to be

Speaker 1 interested in me

Speaker 1 when they would talk to me, right?

Speaker 2 Because women, in your mind,

Speaker 2 women, oh, they want a more experienced guy.

Speaker 2 They want a guy with more history with dating women, more charismatic, that kind of thing?

Speaker 1 Exactly. Like

Speaker 1 the Fawns or something right like the guy who knows how to treat a woman and and and and

Speaker 2 you need to be able to hit the jukebox and make the jukebox come on just with magic like the font exactly right

Speaker 1 so um i think oh sorry go ahead yeah i i think just missing that um there was i felt like there was something that i just didn't I didn't have or that that women wanted that I didn't even know about.

Speaker 1 And it was,

Speaker 1 I just didn't 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.

Speaker 2 Yeah.

Speaker 2 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.

Speaker 2 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.

Speaker 2 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 it was meant to be maybe

Speaker 2 absolutely i have a richie cunningham vibe um so when we started to work together uh 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.

Speaker 2 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?

Speaker 1 Yeah, I think when we did that exercise where we kind of listed all of, like, tried to make the case for

Speaker 1 why

Speaker 1 women aren't into me. And I had to prove that.
And it was, and it was very clear to me. I'm a very logical person.
I, you know, I'm a software engineer and

Speaker 1 I think about things in a very, very logical way. And

Speaker 1 you need to have data to prove

Speaker 1 why a certain thing is true, right? It's not just true because you feel it. And

Speaker 1 so I think when we went through that exercise and I just realized

Speaker 1 there wasn't the data to really support these beliefs that I had around why women didn't want me.

Speaker 1 Like,

Speaker 1 like even when, like, for example, even when I was, you know, a bit heavier than I was now, than I am now, I was,

Speaker 1 you know, I was in a relationship with a woman and she actually told me that she thought I was attractive, right?

Speaker 1 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,

Speaker 1 and so, yeah, it was things like that that, that, that helped me.

Speaker 1 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

Speaker 1 you do have something to offer like you said right right and um

Speaker 1 but but it definitely helped me help help give me a um

Speaker 1 i think sometimes when you when you when you're able to name something

Speaker 1 it all of a sudden it becomes something that's uh that's

Speaker 1 like you're able to uh

Speaker 1 overcome it right right and and i feel that that's kind of what we did was we we we kind of or you helped me do was really like

Speaker 1 actually call the thing for what it really was and then and then i could i it i could um

Speaker 2 i could find a way to to get to uh 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

Speaker 2 And if you remember anything from the list, what are a couple of things from your list that when you think about them make you puff out your chest a bit and say, yeah, that's pretty damn awesome.

Speaker 2 That sounds like a good catch. Do you remember?

Speaker 1 Yeah. Like, I think

Speaker 1 I'm a, I'm a, I'm, you know, amateur singer-songwriter. And I think, you know, a lot of women would like a guy who can serenade her, right?

Speaker 2 Yeah.

Speaker 1 It's certainly the case for my current girlfriend. So she loves that about me.

Speaker 1 And

Speaker 1 there are

Speaker 1 other things like

Speaker 1 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

Speaker 1 be outdoors.

Speaker 1 I even love hiking.

Speaker 1 Connell, I know you're not a hiking fan.

Speaker 2 Hiking should be be illegal. That's all I'm saying.

Speaker 1 And then

Speaker 1 I love sailing, and I even got my sailing certification. And so

Speaker 1 I think those are things that

Speaker 1 a woman might be interested in, or definitely would be interested in, right? Or even would like to share with me.

Speaker 2 You made a great insight a minute ago where you said, I'm a logical guy. I like data.

Speaker 2 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.

Speaker 2 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.

Speaker 2 Sorry, reasonable doubt. It wouldn't get to the jury.
The judge would be like, get this shit out of here.

Speaker 2 There's no evidence of it. Or at least not evidence that every woman's not going to be into you.

Speaker 2 And you obviously got a lot of a wonderful woman in your life to prove that that old belief false. We got confidence, which is really important.
Women want a man who has confidence in himself.

Speaker 2 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.
Think if you would about it could be your

Speaker 2 first messages or your first date with your now girlfriend Jennifer or anybody else you met along the way. What

Speaker 2 flirting

Speaker 2 or how to talk to women advice can you share with our listener? Things that I help, hopefully helped you get better at?

Speaker 1 Yeah, I think,

Speaker 1 you know,

Speaker 1 at one point we talked about values, right? And one of the values that was really salient for me was playfulness.

Speaker 1 And

Speaker 1 that's something I really, that's actually one of the reasons I really liked

Speaker 1 your opener, which is what, which what I used with

Speaker 1 my now girlfriend of the time.

Speaker 2 The dating app opener.

Speaker 1 The dating app opener. That's right.

Speaker 1 And so

Speaker 2 may I read it? Let me read it.

Speaker 1 Yeah, go for it.

Speaker 2 And not literally yours, but here's what I say. Yeah.
So I call this the time traveler opener or the back to the future opener.

Speaker 2 So I'm watching Back to the Future a few months ago, and I'm like, you know, it'll be fun to try. And so I just started experimenting with this.

Speaker 2 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?

Speaker 2 Our love depends on it.

Speaker 2 Gia writes me, hey, Connell from 2031. I've been expecting you.
Ask away. It's a little red heart.

Speaker 2 Hey, Gia.

Speaker 2 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?

Speaker 2 And then she says, Connell from 2031, how could you forget we met at a wine bar? And so then the first date closes.

Speaker 2 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 traveler opener or a variation of that.

Speaker 2 And so that's a fun, playful way to break the ice with a woman on a dating app.

Speaker 2 Tell us how Jennifer responded to that or how you felt about using that.

Speaker 1 Yeah. So I modified it a little bit because it just from her profile, it seemed like she was more of a boba person.
So I said, hey,

Speaker 1 so I said, hey, yeah, did we get ice cream or boba? And

Speaker 1 she actually responded,

Speaker 1 but actually you can get them both at the same time. It's called a boba float.
Okay. And so, and I'm like, oh my gosh, how could I? That's so like, how could we have forgotten?

Speaker 1 We were fighting about nothing the whole time. Anyway, it was just like, and then we had this really bantery conversation about that.

Speaker 1 And I think the thing I really like about that opener, and it also worked very similarly with other women on the dating apps, was

Speaker 1 it just

Speaker 1 sets the conversation up to be very playful from the very beginning.

Speaker 1 So you're like, like just the, 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 now girlfriend was with me on the app.

Speaker 1 And then, and then, you know, I can, we can have a nice banter around that thing. And,

Speaker 1 and, um,

Speaker 1 uh, so I actually used it a lot because I really liked that aspect of it

Speaker 1 so much better than just asking someone how their day

Speaker 1 was going.

Speaker 2 Right.

Speaker 1 And then that's so boring. And she told me later, like she showed me her hinge afterward

Speaker 1 that she had hundreds of messages from guys like,

Speaker 1 that she hadn't even like read.

Speaker 2 They were all unread.

Speaker 1 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.

Speaker 1 Cause, you know, most guys are just saying like, hey, gorgeous.

Speaker 2 Right. How are you?

Speaker 2 Yeah.

Speaker 2 What are you up to? How was your weekend? Right.

Speaker 2 I'm so glad to hear that. Not just because of how you and she ended up together, but

Speaker 2 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.

Speaker 2 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.

Speaker 2 That's essentially flirting is literally defined, I believe, in Webster's as playing at love.

Speaker 2 It's light 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.

Speaker 2 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 you sent a great message to Jennifer that way.

Speaker 1 Can you tell us about your first date?

Speaker 2 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.

Speaker 2 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?

Speaker 1 Yeah, I think

Speaker 1 the biggest thing

Speaker 1 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,

Speaker 1 I was, 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 some reason, that was very, very important.

Speaker 1 It's like, like, she needs to like me. It's very, very important.
And so, like, and so I found myself

Speaker 1 saying things that weren't me because I thought that's what she wanted to hear so that she would like me. And, um,

Speaker 1 and uh,

Speaker 1 I had a different,

Speaker 1 a completely different

Speaker 1 experience with in with this date was that I

Speaker 1 mean, when I first saw her, I mean, she was beautiful and I was very attracted to her.

Speaker 1 And I really, I definitely really wanted it to work out, but I didn't have this sense of panic that it wasn't and that this this that my future happiness depended on her liking me, right?

Speaker 1 Um, and so that really allowed me to be just stay in the moment and

Speaker 1 then

Speaker 1 have a conversation with her as myself.

Speaker 1 And it turns out she likes the real Tony. So

Speaker 1 I think that was something that

Speaker 1 made the date

Speaker 1 very fun for me.

Speaker 2 Didn't you tell me that you were her first, first date in a long time?

Speaker 1 Yeah, I was her first date in first first date in 13 years wow

Speaker 2 yeah think about the impression you had to make on her uh the the you're bringing to her a romantic table to make her go okay i'll i'll take i'll actually meet this guy even though it's been 13 years that's incredible i know the the interesting thing is i don't even think she thought it was a date she just She wanted,

Speaker 1 she had tickets to this concert that she wanted to to take someone who would appreciate it. And since she knew I was a musician, and

Speaker 1 because I had a picture of me playing guitar on my profile,

Speaker 1 she

Speaker 1 invited me to this just to share it with, or just so that the ticket wouldn't get wasted.

Speaker 1 But I certainly thought it was a date.

Speaker 1 And we

Speaker 1 just connected and

Speaker 1 had a great time.

Speaker 1 And it ended with a steamy first kiss. So,

Speaker 1 yeah, it was wonderful.

Speaker 2 What was the best moment from the first date? Or was there a do or die moment?

Speaker 2 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 that you just went there?

Speaker 2 What was the highlight moment that you think was like your favorite memory from that first date?

Speaker 1 I think for me, it was

Speaker 1 so

Speaker 1 we were, we were sitting, it, 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

Speaker 1 so,

Speaker 1 but we were all wearing headphones, and that's how everyone was hearing it. So, you could go anywhere on the beach and still listen to the concert.

Speaker 1 And the guy, the, the, the artist encouraged us to do that. So, um, 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.

Speaker 2 And then

Speaker 1 I reached down and took her hand. And like, I think for me, that was the, that was the first time I,

Speaker 1 with her, that I, I,

Speaker 1 I don't know, made it, made a very,

Speaker 2 um,

Speaker 1 explicit

Speaker 1 gesture that I was, uh, that I very, that I liked her and that I really, um, really was into her.

Speaker 1 And um, she

Speaker 1 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.
Cause, like, wait, what if she,

Speaker 1 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,

Speaker 1 uh, like we walked along the beach and uh then we walked up to the uh the

Speaker 2 the

Speaker 1 get closer to the to the to the person who was playing piano and just standing there uh 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 at least 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

Speaker 1 that we were that she was enjoying my my

Speaker 2 my um 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

Speaker 2 I just took a new online dating photo of me from my profile of me on the beach and it's just women are like oh yeah I bet

Speaker 2 get

Speaker 2 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.

Speaker 2 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?

Speaker 1 Right. Yeah.

Speaker 1 It was, yeah,

Speaker 1 we had those photos

Speaker 1 that show that part of me.

Speaker 2 Yeah, it's like, let's market ourselves, but in a genuine, real way. Like, hey, this is the real me.

Speaker 2 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?

Speaker 2 Like, compared to where you were before

Speaker 2 versus now, how do you feel about Tony as a man? And how do you feel just being in this relationship with Jennifer?

Speaker 1 Yeah,

Speaker 1 it's weird. Like, It's like I can't even

Speaker 1 remember what that old Tony

Speaker 1 was like, what it was like to be him, you know.

Speaker 1 It's

Speaker 1 like, you know, we've been dating for like two months now, and

Speaker 1 it's been so much fun and

Speaker 1 just it's made me

Speaker 1 so happy.

Speaker 1 And it

Speaker 1 it's and it's

Speaker 1 I am I feel

Speaker 1 in the past

Speaker 1 even even in my marriage I don't think I was

Speaker 1 I think I was always settling for for

Speaker 2 for

Speaker 1 less than I deserved not like not like in a

Speaker 2 um

Speaker 1 pretentious way, but like

Speaker 1 but things that

Speaker 1 but

Speaker 1 the things that weren't good for me, I guess is the right way to say it. And and

Speaker 1 but with

Speaker 1 with Jennifer

Speaker 1 I feel

Speaker 1 I don't know, I feel like I'm not settling for anything and

Speaker 1 we

Speaker 1 we connect connect on so many different levels.

Speaker 1 We share a passion for cooking and food. And

Speaker 1 so we connect on that.

Speaker 1 We both love our kids. And we connect

Speaker 1 about that. And it's something that

Speaker 1 we share. And it's something that we appreciate about each other.

Speaker 1 And we just have so much fun together.

Speaker 2 And

Speaker 1 it's been like, it's,

Speaker 1 it's been so,

Speaker 1 so

Speaker 1 incredible. And I almost, I can't, you know, can't, I pinch myself

Speaker 1 because it's been so long, right? It's been

Speaker 1 been so many years since I felt that. And

Speaker 1 it just doesn't seem real, but it is.

Speaker 2 Incredible.

Speaker 2 You're a lucky guy. Don't forget, though, she's she's a lucky woman.
You're both lucky to have found each other, two incredible people.

Speaker 2 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,

Speaker 2 and isn't naturally extroverted, if he doubts himself or just doesn't know how to flirt,

Speaker 2 what final piece of dating advice would you give a guy listening to this to take a step in the right direction?

Speaker 1 Yeah, I would say that there are,

Speaker 1 as Connie, you told me, an abundance of women out there that are

Speaker 1 into a guy like you.

Speaker 1 And

Speaker 1 it's not impossible. Like, I remember seeing the movie Notting Hill, right?

Speaker 1 And there's that scene where

Speaker 1 he says,

Speaker 1 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

Speaker 1 lucky, I can't remember exactly what he said, but he's 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?

Speaker 1 Just so impossible. But I disagree.
I disagree with him.

Speaker 1 What was the name?

Speaker 1 The character.

Speaker 2 Hugh Grant. Anyway,

Speaker 1 I disagree with that.

Speaker 1 I think

Speaker 1 it is possible to find that

Speaker 1 for yourself.

Speaker 2 Incredible. Well, thanks so much for being here.

Speaker 2 Back up.

Speaker 2 Thanks so much for being here, Tony. You have given us so much hope and insight.
And

Speaker 2 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.

Speaker 2 Thanks for being here today.

Speaker 1 Of course. Thanks, Connell.

Speaker 2 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.

Speaker 2 And if you're not into that, no worries. Keep listening to the podcast.

Speaker 2 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.