How to Get a Girlfriend with Connell Barrett
Tongue-Tied with Women? Become a Funny Flirt with 3 Simple Moves and Get Her Giggling! (Live Coaching with Jake)
Tue, 20 May 2025
Do you feel tongue-tied around attractive women? Want to be funnier and flirtier, but you’re not sure how? In this live coaching session with his client Jake, dating coach Connell Barrett shares 3 simple moves to master funny banter and playful flirting. You’ll hear Jake go from awkward silences to laugh-filled connections, learning how to be funnier and way more attractive—without any weird pickup-artist tricks! Because women are attracted to your most authentic self.You’re About to Learn:03:01: Why Women Tell Guys Like Jake, “Sorry, Not Feeling a Connection”07:11: How to Lightly Tease Women in a Way they Love15:32: The Right Way to Use Sarcasm on a Date—and the WRONG Way21:03: An Easy Technique to Never Run Out of Things to Say25:39: 3 Ways to Ace Your Next Speed-Dating Event… and Get Phone Numbers!34:58: The First-Date Question to Ask Every Woman43:57: The Secret to Unlocking True Charisma, While Being Authentic54:57: 1 Simple Move to Get Out of Your Head and In the Zone on DatesFOR A FREE STRATEGY CALL WITH CONNELL TO FIND OUT IF DATING COACHING IS RIGHT FOR YOU: http://www.datingtransformation.comWANT A FREE COPY OF CONNELL’S NO. 1 AMAZON BESTSELLING BOOK, “DATING SUCKS BUT YOU DON’T”? EMAIL CONNELL AND WRITE “FREE BOOK” IN THE SUBJECT LINE AND YOU’LL GET IT INSTANTLY:[email protected]
Chapter 1: Why do women sometimes feel no connection with men?
You might find out her first concert was Nickelback. And you could say, what? Your first concert was Nickelback? Well, you know why they call them Nickelback, right? Their music's so bad, everybody wants their Nickelback when the show's over. Welcome back to the How to Get a Girlfriend podcast. I am your host, dating coach and author, Conal Barrett.
I am here to help you flirt with confidence and get a great girlfriend all by being authentic. Women like you for you. No sketchy pickup artist moves needed. I coach gentlemen, good guys, intellectual types, white collar guys, sometimes shy introverts. And I have a shy introvert here today for you to meet.
You're about to listen to a live coaching session I just did with my brand new client, a guy named Jake. Jake is 31. He's an educator. He lives down in the South and he is a very intellectual, logical guy. And he struggles to be flirtatious on dates and when talking to women. He struggles with what to say, the right thing to say, and he wants to be funnier.
He wants to be more charming and funny and more flirtatiously attractive to women. And that's one of my specialties. I love guys getting really good at banter, at being able to make sparks happen on dates so we can stay out of that friend zone. And you're going to get to meet Jake today. This is a really good episode or a good coaching session that I recorded with his permission, of course.
And you probably are going to relate to Jake because he tends to default to analytical, logical conversation, but not quite know how to get on that flirty, funny wavelength. And today I talked to him or in this session, this coaching session, We went over some three or four of the core basic ways to be funny and flirty with women, being sarcastic, being playfully teasing.
I also gave him a real simple way to never run out of things to say on dates so that he and you can make women laugh, but do it in a flirtatious way. So being funny, being flirty, it's very learnable. So stay tuned for that. And a quick housekeeping thing. I'm about to take three months off of coaching And just start writing my second book.
My first book, Dating Sucks But You Don't, came out about four years ago. I'm about to take three months off to work on my second book. My second book is all about flirting. So I'm about to close my coaching slots. But I will be coaching for another few weeks.
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Chapter 2: What are effective ways to tease women?
So if you like this podcast and you are looking to talk to me about how dating coaching works and you want to go from struggling with flirting and what to say or just struggling with self-confidence and becoming a lot more confident and really good at flirting and making some sparks fly like Jake is going to learn today, just go to datingtransformation.com.
You can book a free call with me and you and I will get on the phone and I'll give you a plan. And we'll figure out if dating coaching is right for you. And even if we don't work together, you'll get a free fun call out of it. And I can help you get clear on how to get your girlfriend.
So go to datingtransformation.com and book a free call with me because I'm about to stop taking clients for several months while I write book number two. Okay, let's get to it. Let's talk to my client, Jake. Enjoy. All right, Jake, let's get to it, man. What are the dating problems you're looking to fix? What are some of your goals? How can I help you, man?
Yeah, so, Connell, one of the things I've been noticing I've been struggling with probably for a very long time, but it's just become more noticeable to me now that I've really kind of started to focus on dating a little bit, is kind of initiating humor, flirtation, teasing, that sort of thing, just in not only just day-to-day conversations, but specifically with women that I want to be dating or women that I am dating.
So I've gotten a little bit better at least with just kind of being able to hold interesting conversation, asking intriguing questions, that kind of stuff. But the conversation just kind of goes like I'm talking to like just anybody else. If it's a friend, if it's a family member, like it's like I don't really change a whole lot with the exception of an occasional comment.
So flirting and basically the teasing aspect is challenging for me. And the funny thing is, is I can do it if somebody else initiates it. Like I have a pretty decent idea of how to respond with that kind of stuff. But for whatever reason, I just kind of have a block when it comes to figuring out, okay, like not only when to initiate it, but what are some like kind of good times to do that?
What context are we talking about? Are we talking about a first date? Are we talking about a conversation at a party or a social event? I'd probably say a little bit of both, actually.
So it's kind of like even if I'm on the date and I've peaked the woman's interest a little bit and I'm just kind of getting to know her a little bit, it's more of a get to know you rather than kind of building that romantic tension, so to speak. And I've definitely noticed that because I've gotten a lot of like, hey, this was great, but I'm just not feeling that spark.
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Chapter 3: How should sarcasm be used on dates?
Okay, got it. How do you currently flirt or do you intentionally?
So intentionally compliments, I've started to do a little bit more from like when I was, I can't, I think when I was reading your book,
you were talking about like the challenge to do like, do you mean bestselling book dating sucks, but you don't buy Conal Barrett published by Simon and Schuster. Exactly. Okay.
Yeah.
And so I know that's okay.
So essentially it was like, I got to the homework assignment on one of the chapters or it was like, give compliments. So I was trying to be a little bit more aware of like, okay, like I saw a girl today that was at my dog daycare that had a little tattoo of a paw on her arm. And so I'm like, okay, this kind of sounds like, it seems like it's the Her dog. That was my assumption.
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Chapter 4: What technique helps to never run out of things to say?
I'm like, oh, is that the tattoo of your dog's paw? That is really cool. And she got like really excited and started talking about it. So I've been doing good with that. And occasionally, like when people initiate a little bit of teasing or a little bit of like sarcastic sense of humor, I can kind of dish it right back.
So something I'm trying to think of an example of when that happened recently, but it's blanking right now.
No worries. So we've talked about teasing so far on this call and flirting. Now teasing is a kind of flirting. Yes. Is that what you want to focus in on specifically teasing flirting? I would probably say so. Yeah. Okay. Because there's many, many flirting tools. Teasing is a great, great, a great one to choose. So let me ask you this.
How do you tease your friends or people close to you when you are in that teasing zone? Or do you?
Chapter 5: How to excel in speed-dating events?
I can do it with my friends, sometimes my closer friends. So like I have one friend who he's also a very sarcastic sort of person. And so generally the primary way I'll tease him is... about his teaching style, so to speak, because he's a teacher. And essentially, he's very sarcastic with his students and everything like that.
So I'll kind of poke fun at him with some of the things that he does because he knows he's kind of a dick, so to speak, with some of his students. So it's kind of like something like that. I can't remember a specific example.
Great. Here are a couple rules of thumb on teasing. Mm-hmm. Think of it like it can and does work with many women. Not all. But many. And I think it's something built into our systems. It's like imagine the 10-year-old boy who's got a crush on the girl sitting in front of him in grade school, pulling her pigtails, pinching her because he likes her. It's a way to show, hey, I like you.
And I'm going to tease you to show you that. So I think of teasing as something very natural and normal and healthy, as long as it's done with good intentions, which of course it would be with you, as opposed to the old school pickup guys, which are like neg, you know, call out her crooked teeth and say she looks like Bugs Bunny to make her insecure. Like that bullshit is so... 2000 late.
It's really old. And I know that's not what you're asking about, but I do want, I just wanted to make that differentiation. Flirting is a great, as long as it's innocent and good intention. So here's how we do it in a way that can be very effective and fun is think of it. Like, what can I, what can I gently nudge her about?
And we want to choose a topic that is not something that a reasonable person would get upset about the underlying truth. For example, here's what not to do. You're on a date and she's had three or four drinks and you, not you, Jake, but the royal you, you say, oh boy, that's your fourth one. What are you, some kind of raging alcoholic? Yeah. Well, don't say that.
Some women might laugh at that, but other women might have that as a sore point. I had a client do that once, or a guy who came to me right before he started working with me. He told me that story, and he said that it instantly killed the date because she took that topic seriously. So we want to tease about surface-level things. Things like her taste in music.
Perfect example.
I love hating Nickelback. You might find out her first concert was Nickelback. And you could say, what? Your first concert was Nickelback? Well, you know why they call them Nickelback, right? Their music's so bad, everybody wants their Nickelback when the show's over. And you tease her about what a bad taste in music she has, or at least what a sad choice she had for her first concert.
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Chapter 6: What first-date question should you always ask?
Any reasonable person's not going to get offended by that. So tease about things like taste in movies, taste in music. You could tease about little things like... Little verbal things. If you feel like she's a fairly confident person being articulate, you could tease her about how she pronounces things.
I remember on my second date with my girlfriend, Jess, I heard this Connecticut kind of pronunciation. She wouldn't say soft. She would say soft. Have a little bit of wah in there. And I said, ooh, I love that trashy Connecticut accent, which by then we had a good rapport. And so I'm not calling her trashy, of course. I'm calling her accent a little trashy.
So you want to choose things like taste in movies, food, music, TV shows, or surface level behavioral things. Yeah. As opposed to alcohol or weight or attractiveness. Here's one more what not to do. My client, I'll call him, this is not his real name, I'll call him Chris. My client Chris recently had a really good first date. And then by text, he tried a little too hard to tease a woman.
She's about 10 years older than he is. She's almost 40 and he called her a cougar. She got very upset and basically it was over.
Yeah.
So understandable. Women of a certain age might be uncomfortable about that kind of joke. So does this help?
Yeah, I would definitely say so. And it's interesting you bring up the pronunciation because I actually had somebody on a little bit of a different story, a dating app. One of her hinge prompts was don't hate me if I pronounce the L in salmon. So it's Solomon, basically. And so I was thinking about that, actually. I'm like, how do I use this to my advantage here? Because I don't say it like that.
So I think that actually, I think that probably would help in that aspect of things.
Yeah, looking for little things like that, especially you as an educator, very articulate. I'm assuming you're going to be very attracted to women who are well-spoken and vice versa. So verbal people like you, like me, very conversational people, this is a fun area to explore.
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Chapter 7: How can one unlock true charisma while being authentic?
Mm-hmm.
And do it gently. You know, she might say something like, the love of my life from the teens, a woman named Alex, who I dedicated my book to. There's a whole chapter about her in my book. Her name is Alex. And I remember I was teasing her about how she pronounced, she couldn't pronounce the word rural, which is a hard word. She kept saying rule. I'm like, no, it's rural. Rural.
It just became a silly little back and forth. And so I'm reading her and, you know, you always want to read the room. and kind of notice how, oh, is this teasing working? Is she giggling? Is she punching me back, but good-naturedly? Or does she like... not play with you back. So it's like tease and then kind of notice and watch and see how she responds.
And I guess that actually is the next question I wanted to ask about that too. So if it is something where it's like you make the attempt to tease and you notice it's taken maybe a little bit more poorly than you'd hoped, how do you recover from that? Because I think that's one of my challenges there is being a little nervous to do it
First, just because I'm not really sure what the reaction is going to be.
Yeah, that's a mindset challenge for you. I remember us talking about this before. You want to have the... First, you want to remind yourself, I'm the boy, and it's my job to go first. Yes. To be ready to lead the dating dance. And so don't wait for the green lights to tease and joke, if that's authentic to you, if that feels like it's Jake.
That said, so it's just a little bit about doing the thing that's a little scary. Right? I'm going to tease her now. Yeah. But... But you then said, oh, but what if it isn't taken well? It kind of depends on what her reaction is. If it just sort of doesn't land, but no big deal, ignore it and just move on. If she pushes back and says, hey, that's not funny.
or pushes back a little bit, then fall on your sword and say, well, you know what? Sometimes I'm not funny. That was one of those moments. I apologize. If you offend her. It's hard to offend on surface level things like Nickelback sucks. It is hard to offend. But if her dad is Chad Kroger, okay, maybe. Yeah. Maybe you find out, oops, then you could just kind of own it.
And owning it can actually be pretty attractive because she's like, okay, he screwed up, but he took it and accepted responsibility. So if it's just more like it didn't land type thing, don't even worry about it. Just move on. Maybe try one more time. But if she's like, hey, wait a minute. That's not funny. You go like, you know what? Sometimes I put my foot in my mouth. I apologize.
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Chapter 8: What is a simple move to get out of your head on dates?
If I'm finding something that I personally don't like teasing about, it can be kind of a good way of doing that as well. So like with other forms of flirting. So I know you had sent me a list the other day of different forms of just like humor and things like that.
So if I were to be doing something like sarcasm or something like that, how would that be a little bit different in terms of things like that?
Sarcasm, I mean, I'm sure you know what sarcasm is, right? It's just saying the opposite of what you mean with a little edge in your voice and looking for an opportunity in the moment when that presents itself on a date or in a conversation with a woman who you just met. What I like to do, here's a bit of an advanced move. you can combine sarcasm with a sincere compliment.
These are two flirting tools. It's like crossing the stream in Ghostbusters. Cross the streams. It can be extra powerful. And maybe you... I don't know. Here's a hypothetical. You're on the first date, five, ten minutes in. You're both getting comfortable with each other. She looks incredible. She's put together. She's really cute. Cute outfit. And... She says, oh, what do you think of my outfit?
She's probably fishing for a compliment, which who wouldn't? I love compliments. And you might sarcastically say something like, oh, you definitely don't look absolutely incredible tonight. You're not the cutest girl here. And that sarcasm lets her know you mean the opposite.
Yeah.
And so you're paying her a compliment and you're having a little bit of that sarcastic edge. So you can give a compliment in a sarcastic way. I told my girlfriend, Jess, on our first or second date, I said, just so you know, I definitely don't want to see you again. I don't think you're stunning and witty and sexy and cool.
And I really don't want to take you out for a third date next Saturday night at 9 p.m. Made it very clear what I wanted. Oh, yeah, definitely. And she likes that indirect, fun, bantery humor. So you can use it that way. Or you can just use it in an organic moment as it comes up. you know, she's running late for the date. She gets there 10 or 15 minutes late. Parking was crazy.
And I don't know, let's say you, I know you don't live there. Let's say you live in Atlanta.
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