“The Best First Date of My Life” — How Tony Learned to Flirt and Won Jennifer Over
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How did Tony feel when he re-entered the dating world after a long marriage?
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 how to flirt.
Welcome back to the How to Get a Girlfriend podcast. I am your host, dating coach and best-selling author, Conal 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 overcome 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 I... I had a lot of confidence issues and, and I think because of that, I made some really bad decisions 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, and, 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 like 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, I had no idea what women were expecting of me or, or what, or, 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, um, and it seemed like everyone around me knew and, and I didn't know. So, um, And then even just feeling like I was the type of guy that women would want to date was a big problem. So those are some of the big struggles I had.
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... 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, about, about my body there, but, um, definitely that was a, that was something that was a concern. I think also, um, I'm, uh, I'm a, I'm a single dad and, uh, didn't, didn't know how many women would be into that. Um, I, I also felt like, um, Um, because I, I didn't have a lot of dating experience that just women weren't going to be, uh, uh, interested in me when, when, when, when they would talk to me. Right.
Right. Um, um, because women in your mind, women, oh, they want a more experienced guy. Right. 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.
You need to be able to hit the jukebox and make the jukebox come on just with magic like the Fonz.
Exactly, right. I'm sorry, go ahead. Yeah, I think just missing that, I felt like there was something that I just didn't have or that women wanted that I didn't even know about. And it was, or I just didn't 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, 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?
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Chapters
3 chaptersSpeakers
1 identifiedMore from How to Get a Girlfriend with Connell Barrett
7 Texting Mistakes that Make Women Flake Before the First Date (and 7 Easy Fixes)
8 Flirty Things to Say (and Not to Say) When You Freeze Up Around Women
The 10 Most Surprisingly Sexy Things to Say on a First Date
The 7 Lies that Keep You From Approaching—and 7 Tips to Confidently Talk to Women Anywhere
The 10 Texting Commandments: How to Stop Getting Ghosted and Start Getting Dates
21 Flirty Ways to Make Her Feel Authentic Attraction (How to Escape the Friend Zone, Part 2)