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Episode #9

How to Be Flirty, Funny, and Never Run Out of Things to Say

Featuring NYC Dating Coach Connell Barrett
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Learn how to be flirty and funny on your next date, featuring NYC dating coach Connell Barrett.

You know what sucks more than a Vin Diesel movie? When you’re talking to (or texting) a woman you’re into, and you just know you’re being boring. You’re stuck in your head. You ask dull questions in “interview mode.” You’re not sure what to say.

You can feel her losing interest in you, and sure enough—she goes off to find a flirty guy who can make her laugh.

It can make you feel boring, unattractive, and get you stuck in the dreaded “friend zone.”

In this episode of the Dating Transformation podcast, host and dating coach Connell Barrett gives you his secret weapon to be flirty and funny, whether you’re texting a new match on the dating apps, or looking to charm your Saturday night date.

Connell will teach you how to…

✔ Turn a boring conversation into something fun and flirty, using a powerful technique from improv comedy that can transform your flirting skills
✔ Get out of your head and in the moment with women, so you can make sparks fly with your words
✔ Text women in a way that builds a genuine, fun connection that helps you get more dates

And of course, you’ll be able to do all of this as your best, most authentic self—without any creepy “pickup artist” nonsense.

Listen now, to take your conversations with women from dull and boring to funny, flirty… and smash out of the friend zone!

Our Host: Connell Barrett

Founder and Executive Coach of Dating Transformation

Book Your Free Call Today and grab a time that works for you

Get the number 1 Amazon Bestselling book “Dating Sucks, But You Don’t”:

You don't need to be great looking. You don't have to be tall. I mean, if you can be funny on a date that's sexier than six pack abs. - Connell

00:00 Introduction
01:26 You don’t need to be a comedian to get the girl
02:59 Use the core concepts in improv comedy
08:25 Book a call with Coach Connell or Get our best selling book on Amazon Today “Dating Sucks But You Don’t”
09:49 An example of “If this is true, what else is true?” concept
16:11 Another example of “Yes Ending” concept
21:03 Recommended actions to elevate your game

Produced by Heartcast Media

Related Episodes:

Make Sparks Fly

How to be More Confident with Women

First Date Tips for Guys

How to Start a Conversation on a Dating App


Connell: Yeah. I mean, you don't need to be great looking. You don't have to be tall. I mean, if you can be funny on a date that's sexier than six pack abs.


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


Connell: Welcome. Welcome. Welcome back to the Dating Transformation podcast. I am Connell Barrett, a dating coach for men. I help introverted men gain confidence, learn to flirt, get dates and get a great girlfriend all by being authentic. And I want to do a very special, cool, fun podcast, one that's close to my heart, but one that's going to help you if you struggle with. I don't know what to say. Or if you struggle on a date or when texting a woman and you're not sure what to write. And especially if you feel like you're too boring, you're not funny enough. You don't have the funny gene. You you feel like, Oh, sometimes I run out of things to say, I don't know how to create sparks, I don't know how to create attraction. And or if you just get friends a lot, then this is definitely the podcast episode for you because today I'm going to give you my get ready. I'm going to use my marketing talk. My number one secret weapon for being funny and being funny is not required to have a great dating life to get a great girlfriend. I've worked with plenty of clients who aren't necessarily the funniest, quickest guy in the world, and that's okay. You don't need to be a stand up comedian. You don't have to be Mr. Witty. However, you do what you do have to, at least to a point, be late and a little bit playful, positive light and a little bit playful, I think. I think that's pretty much a requirement of success with women in dating. So today I'm going to give you a the cheat codes for being. Witty, playful and just magnetic, creating a funny, flirty spark on the date. That's really what this is about. And yes, in 15 to 20 minutes, I'm going to give you the way the way to do that. I mean, give you 3 to 5 specific strategies to help you do that. And let's get right to it. Let's just get to the good stuff because I just want to help you. Barry, I want to I want when you're texting, I want you to be able to always know what to text or on a date know what to say. So here is a shortcut to getting really fun, funny, flirty conversations going with women. Here's what you want to do. You want to apply the core concepts that are used in improv improv comedy. I've been doing improv comedy for 12 years now. I do improv primarily at a theater here in New York City called The Magnets. I also do it at a place called the Pit People's Improv Theater, and I love doing improv. When I first got into doing improv, I was just doing it as a fun form of self-improvement. I just wanted to get up on a stage and crack some jokes. It seemed really funny whenever I watched the TV show. Whose line is it anyway? It just always had me laughing. And so I'm going to give you the two or three core tenets of improv and help you apply these in your dating life. Because what I found to my great surprise, my pleasant surprise was after I started, I started doing improv around the same time when I was first really working on my dating life back in the late actually 2011 was when I first did improv. 2009 was when I first started hiring coaches because I was introverted. I was struggling with women and dating. I got stuck in my head and I started doing improv and I started seeing some really cool things happening on dates and talking to women. I found myself growing more confident, a lot more presence. Improv taught me how to listen and really hear what a woman was saying and then return the conversation in a fun, funny way. So let me talk about the two or three core tenets of improv. It's going to get a little bit nerdy, a little inside baseball about improv, but I promise at the end of this, you're going to get three, four or five practical tips you're going to be able to use when texting, when talking to a woman on a date approaching and just not knowing what to say, always knowing what to say. Improv helps so much. So here's basically how improv works. Two people get up on a stage and these two people start making up a reality. And the way it works is a concept called Yes. And meaning that you and your scene partner, your fellow improviser, you're essentially starting in a vacuum. You don't know where you are or even who you are. You're inventing the entire performance from scratch. And so when somebody says something like f f myself, and I have a there's a person I do improv with great guy named Lane, if Lane and I are doing a scene together, we're standing there. We don't know what's going on. He might start by saying, Hey, Dad, happy birthday. And now as an improviser, I say yes to that. I don't say it's not my birthday. It's July 4th. My birthday is in a different month. I'm going to say yes to what Lane is putting down. Yes, it's my birthday and I'm your dad. And then I'm going to say and I'm going to add some information. So, for example, Lane might say, Hey, happy birthday, Dad. And I'll say, Oh, thank you, son. It is my birthday, and thank you for giving me this beautiful gold watch. And I might hold out my wrists showing a pretend gold watch. And that's how we build an improv scene brick by brick. So all of a sudden, you're watching two people, a father and a son having a conversation about. That dad their relationship. And it's the dad's birthday. So the concept of improv is. Yes. And please Google. Yes. And Google Improv do some research on improv. And there's a very similar sort of tangential concept related to the improv. And the concept is, if this is true, what else might be true? So for example, if in my improv scene, I it's my birthday and I'm wearing a gold watch. What does it mean about my character if I'm wearing a gold watch, who might wear a gold watch? In other words, if this is true that Connell's playing a father who wears a gold watch. What is it? What else might be true about a man who would wear a gold watch? Maybe I have other gold jewelry. Maybe I'm really into bling. Maybe I just. Maybe I have a gold watch on because I just retired and I go, It's my 50th. It's my retirement retirement present. So we can make assumptions based on information that's going on. So why am I going all into the mechanics of how improv works? These two concepts of. Yes. And. And if this is true, what else might be true? These can really help you and serve you when you're on a date with a woman or when you're texting a girl you just matched with on Bumble or Tinder, or when you approach and you're not sure what to say. You can use the concept of if this is true, what else might be true? Now, let me give you a couple quick real world examples from my dating past.


Woman voice: 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 one Amazon bestselling book Dating Sucks, but you don't. Your 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 sex, 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.


Connell: I remember. Once I started taking improv and then I went out and I was approaching different women out in New York City. I realized all of a sudden I was coming up with some really fun, funny things using these concepts. I remember one day I saw a woman walking down the street with a bunch of shopping bags. Tall, attractive, brunet, stylish, well-dressed. And she had all these shopping bags. And my improv brain basically said, Hmm, if this is true, what else is true? If a woman has shopping bags or if a woman is carrying bags? What might be true about her? Now I'm thinking about this in an exaggerated way, not a literal way. So my brain went to, well, who else has bags, a quote unquote bag lady or a person who's down on their luck? Now. So I remember I walked up to this woman and I said, Oh, hey, I just want to say that your and she had three or four bags under all under her arms. I said, Hey, I just want to say that you're the cutest bag lady I've ever seen. And she immediately broke down to a big smile. So I paid her a compliment. But I also used the concept of improv to say, if she's if she's wearing holding these bags, she might be a quote unquote, bag lady. So there's also a subtle tease that's going on. Right? That's one example of. Yes. Ending. Another example would be, I remember. My very first date after the pandemic ended, I got vaccinated. So I was going out and dating. And I was I was not in a relationship at that time. So the very first date I had after the pandemic ended, we go on a date, really cute girl from Bumble and the yes ending and the and and the using the concept of this. If this is true, what else is true? That began even before we met. We started texting that way. So, for example, on my bumble profile, Bumble profile, I used to have this line I would end it with, I promise I won't send you a dick pic, but I might send you a duck pic. And then I had a little duck emoji and I would get a lot of women who messaged me saying, Ha ha ha, very cute. Do you like ducks? Or sometimes a lot of women would actually send me a duck emoji or an out emoji. But like a little Jeff, that bumble gives you the option of sending. And I matched with a woman named Emma on Bumble, and she liked that line. So she sent me, she said, Hey, I want my duck pick. And then I wrote her right back saying, okay, here's your duck pick. And I sent her a little duck meme. And so so I said, yes. She said, I want my duck back, basically. And I said, Yes. So she actually said yes to my duck line. I said, yes back. And then I ended it by saying, okay, here's your duck pick. And I named him after you. His name is. Her name was. Her name is Emma. So I said his name is Gemma because it rhymes with your name, Winky Emoji. And then she wrote back something like, Oh, my God, I love our duck. We're such good duck parents together. I love, I love. I love our baby boy. Gemma Okay. And then I wrote back, Okay, if this is true, what else is true? If this is our baby boy duck, what might be true? And I wrote back in, You know what I love most about Gemma is Gemma walks just like his mom. You guys have the same waddle. It's so cute. So I'm actually flirting with her. I'm telling her that she's. She's cute. She has a nice walk. I'm also teasing her a little bit by comparing her to a duck. But it's all very playful, very light. And I remember so. So Emma and I went back and forth on lot with lots of fun messaging. And all I'm doing is yes, ending. All I'm doing is saying, if this is true, what else is true? So you know what? I didn't have and very many of these messages, I wasn't asking things like, How's your day? How are you? How was your weekend? Those logical, logical informational messages to many of those who get very boring for women, they don't want to hear too much. How's your day? How are you? Information. Information. Information. Somebody African. I forget the dating code. She said this, but somebody said information and logic is the opposite of romance. What we want is playfulness. Lightness. So this yes end concept from improv created a great, fun banter back and forth with myself and Emma. So Emma and I go out on a first date and we just continue the fun. Yes. And just jokes about our ah duck. I said, Hey, where is Gemma tonight? Did you hire a babysitter to take care of Gemma? And she said, Oh, yeah, I hired a babysitter. And we just had a lot more about fun back and forth. And then she actually said something really interesting to me on the date. She took a moment and we broke out of the banter and she said, You know what I really like about you is she said, I say all this really weird, goofy stuff, and you just go along with it. I loved when she said that because she was basically saying. You are really good at doing improv. You're good at Yes. Ending me. You're good at taking what I say and adding to it. So these concepts can really help you create a spark, create a fun back and forth banter. I'll give you one more quick example from a client, maybe two other examples. I had a client named David, and David was going out on dates, and every so often on a date a woman might challenge you. And he was getting challenged a lot. Not a lot, but he got challenged. And by a challenge, I just mean they might ask you a question. That sound that that might be a little bit of a test. And one of the most common, a common question a guy would get once he starts going on a lot of dates, like my clients go on a lot of dates. And one of the common questions a guy gets is so are you are you some kind of player? Now. The typical the answer most guys would give to that is no, no, I'm not a player. I not at all. I'm not some kind of a player or a pickup guy. But if you take a yes and approach to that question, essentially you would agree with the premise that you're a player or that you have lots of dates and then you would add something to it to exaggerate it. You're not literally saying you're a player. You're essentially going into a role play where you're pretending to be a player, just like Emma and I were pretending that we had a little duck baby. So. So I gave my client, David, a little coaching, and the next time he was asked that, a woman said, So are you some kind of a player or are you going out on five dates a week? He said, Oh yeah, totally. I'm a player. In fact, there's the. Yes, right. And then he added the end and then he said, and actually I have two more dates coming up after tonight, so if we could just speed this up, that'd be great. And I think he and she laughed at that. And I think he even added, actually, two of them are going to be here in 5 minutes. So I'm going to give a rose to one of the three of you. So you better be on your best behavior. She loved that. She loved that. So yet you can. Yes. And even when a woman challenges you or says something kind of goofy and silly, agree that just agree to it. Don't be don't get insecure about it. Lean into it. Another example is one of my clients is on a first date and he yawned. He had a really long day. He was probably under slept and he yawned and she said, Oh my, boring you. And instead of saying, No, no, no, you're not boring me. You're amazing. Everything is great. That answer is okay, but it's not going to create sparks. Instead of that, he said. Yeah, I am so bored. And I actually actually dozed off during your last story about going to the gym today. So if you could spice it up, that'd be great. Now he said it with a smile. He's not literally telling the woman she's boring. It's it's a joke. It's a tease. So but you can use these concepts. Yes. And if this is true, what else is true? You can use this in various situations. And the nice thing about this is some women love to banter, banter, banter, banter. They just love that playful back and forth. My girlfriend Jess and I are like this. We're constantly. Yes. Ending each other and saying, if this is true, what else might be true? So here's one more way you can use it. You can use it as a way to make a fun assumption about a woman who you've just met or are on a date with. So, for example, let's say you have a first date with a woman who is gosh, I don't know. She's she works for I once had a first date with a woman who worked for Facebook and. And at the time, Facebook was really taking a lot of heat for all the like the hate speech and and political ads and Mark Zuckerberg. Zuckerberg was taking a lot of taking a lot of shit. So she said, Oh, my job. I work for Facebook. And I said, Oh, really? And so I said, okay, yes, yes to that. And then I said to myself, Well, if she works for Facebook, what else might be true? And my brain went to the idea that Mark Zuckerberg was being was being framed as this evil bad guy. Right. So I think I said something like, So what's it like working for a James Bond villain? Or maybe it was something like, So what's it like working for Satan himself? Does Mark Zuckerberg have does he have a forked tail and hooves or is that just in photos? And she she actually agreed with me that she dislikes a lot of stuff Facebook does. So it created a fun banter and spark. And the good news about all of this is the concepts of yes ending. And if this is true, what else is true? That you don't have to be mister Quick witted. You don't have to be a stand up comedian. These are basic comedic building blocks that can help you dial that flirty limiter up a lot faster. So here's what you want to do after this podcast. I highly recommend, if you've never done this, highly recommend you find a place to take an improv class. You can take them online. If you live in a city that has an improv community, take them in-person. That's the best way to do it. But if you can't take them in person, find some online resources. If you happen to live in New York City, Chicago, or L.A., you'll definitely be able to find a theater. I'm a big fan of the Magnet Theater in New York City for both online and in-person classes. And the other cool thing about improv is just forget about dating for a second. It just makes you more playful, makes you quicker on your feet, makes you funnier. And once you can go on a stage and and have a fun, funny, funny interaction with somebody, gosh, it really stretches your social comfort zone and you feel so much more at ease and present and playful. Improv teaches presence, listening, playfulness, jokes, vulnerability, sincerity. All of these things that improv helps you to develop. They're all valuable virtues in dating, in approaching and connecting, and most importantly, and just being authentic. That's what I love about improv, among all other things, is that they basically say, Bring your personality, your life experiences into these scenes, into our fun playtime, and I want you to do the same thing with your dating life. Bring your authentic best self into your dating life. So that's my quick primer on how to be funnier. Flirty are quick witted. Don't try to be funny. Just practice the concepts of Yes. And. And if this is true, what else is true? And then jump on YouTube. There's a lot of great videos, a lot of great books about the art of improv, and you'll be able to apply a lot of these things in your dating life. Okay. That's it for today's episode. Yeah. Remember? Beautiful, cool, wonderful, intelligent, awesome women. They already like you. They just have to meet the real, authentic. You. Talk to you next time.


Woman voice: Thank you for listening to the Dating Transformation podcast. For lots of free tips, videos and other goodies. Go to Dating Transformation Icon. See you next time.


Connell: Produced by Heartcast media.

Get Transcription
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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