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The New Way to Confidently Approach and Connect with Women (Part 4 of 5)

Featuring NYC Dating Coach Connell Barrett
listen on Spotifylisten on Apple podcasts

Odds are, you see women you’d love to meet at bars, grocery stores or the gym, but you never approach them. Fear holds you back. You don’t know what to say, and you don’t want to seem creepy. It’s frustrating… but fixable! In this episode, host Connell Barrett—who has approached thousands of women in his 12 years as a dating coach—shares a new way to confidently meet women IRL. His Authentic Approach Technique will teach you exactly what to say to women, so you can get numbers and dates and find an incredible girlfriend. And you’ll talk to women with charm and authenticity, NOT with sketchy pickup tricks.

In this episode, dating coach and bestselling author Connell Barrett will discuss:

(2:35) The 3 Simple Ways to Approach Women Almost Anywhere

(6:30) Why Women Hate Scripted “PUA” Tactics

(7:15) Why Connell’s Authentic Approach Technique is Basically Rejection-Proof

(8:05) The Night Connell Got 3 Numbers from 3 Wonderful Women

(11:50) The Approaching Mistake that Gets You In Your Head

(12:50) How to Meet Women Using a Power Compliment

(16:42) The Mindset Shift that Destroys Approach Anxiety

(19:42) How to Meet Women by Asking the Perfect Question

(22:30) A Great Approach Opener to Use at the Gym

(27:53) How to Meet Women with A Funny, Flirty Icebreaker

(36:30) How to Be Authentically Attractive, NOT Creepy

(41:15) How Connell’s Client Taylor Approached and Made Out with a Woman in Under 10 Minutes

(43:49) Your Approach Mission for this Episode

Are you ready to confidently meet women and get numbers and dates? Listen now!

Listen to part 3 here.

BOOK A FREE STRATEGY CALL WITH CONNELL TO LEARN HOW TO CONFIDENTLY FLIRT WITH WOMEN BY BEING AUTHENTIC (NO SKETCHY PICKUP MOVES NEEDED):
https://www.datingtransformation.com/contact

TO GET FREE ACCESS TO “THE FLIRTY 30,” 30 CHARMING QUESTIONS TO ASK WOMEN ON DATES, ON THE APPS, AND WHEN YOU APPROACH:
https://www.datingtransformation.com/FLIRTY30

"Be the charming, authentic man who confidently sparks conversations anywhere. Your natural charm will have her telling her friends." - Connell Barrett

"Use a genuine compliment, relevant question, or unique observation to initiate conversations." - Connell Barrett

Featured in the episode

Connell Barrett

Founder and Executive Coach of Dating Transformation

Website: https://datingtransformation.com

Instagram: https://www.instagram.com/datingtransformation

Chapters

00:00 - Intro

2:35 - The 3 Simple Ways to Approach Women Almost Anywhere

6:30 - Why Women Hate Scripted “PUA” Tactics

7:15 - Why Connell’s Authentic Approach Technique is Basically Rejection-Proof

8:05 - The Night Connell Got 3 Numbers from 3 Wonderful Women

11:50 - The Approaching Mistake that Gets You In Your Head

12:50 - How to Meet Women Using a Power Compliment

16:42 - The Mindset Shift that Destroys Approach Anxiety

19:42 - How to Meet Women by Asking the Perfect Question

22:30 - A Great Approach Opener to Use at the Gym

27:53 - How to Meet Women with A Funny, Flirty Icebreaker

36:30 - How to Be Authentically Attractive, NOT Creepy

41:15 - How Connell’s Client Taylor Approached and Made Out with a Woman in Under 10 Minutes

43:49 - Your Approach Mission for this Episode

47:56 - Outro

Continue to part 5 here.

TRANSCRIPT

Connell Barrett:
Pretty sure I started puberty watching Jennifer Beals dance in Flashdance. Welcome back to the How to Get a Girlfriend podcast. I'm your host, dating coach and author, Connell Barrett. I'm here to help you confidently flirt with women and attract your dream girlfriend, all by being authentic. No toxic pickup tricks needed. Thank you for being here with me and for letting me be your dating coach for the next 30 minutes or so. And I'm wondering, do you sometimes struggle to approach a girl you might see out in the world? You'd love to talk to her, but you're just not sure what to say. Maybe you're like me back in the day when you saw a woman who just caught your eye at the gym or maybe at a bar or coffee shop.

Connell Barrett:
Back in the day for me, grocery stores, but you never or rarely ever approach because you just don't know what to say. You're not sure what to say to make it go well, and you're also afraid you might come off as awkward or maybe even creep her out. And I have been there. Let me tell you. I used to have the worst approach anxiety in the world. There's a story that opens my book, dating sucks, but you don't, about the very first night I ever went out to approach women. This was back in 2009, and I was so nervous. I actually had to go into the men's room stall at this club before talking to any women because I had a panic attack.

Connell Barrett:
I started hyperventilating. I was so afraid of rejection. I was so afraid of not knowing what to say and how that was gonna get me rejected, and I was just full of fear. So I know how you feel. And the good news is, though, that if I can get great at approaching and flirting with women, then so can you. And you don't need to be a dating coach with 12 years of coaching experience either to do it. You can just do it very, very soon, like tomorrow, tonight, this weekend. In this episode, I wanna help you do that.

Connell Barrett:
I wanna give you a really elegant, simple way to confidently talk to women anywhere. And I'm gonna give you 3 simple approaching options. I'm not gonna tell you exactly what to say, but I'm gonna give you 3 options. It's like choosing your own adventure. When you see a woman, you're gonna have 3 simple options. You can choose the approach that you think is best for that moment, and this is gonna make it easy for you to have conversations with women, and it's gonna make it actually hard to get rejected. It's gonna be difficult to get rejected. So you're always gonna be able to know what to say.

Connell Barrett:
You'll be able to approach with growing confidence and not having to use these scripted, planned pickup artist type lines. I'm actually gonna give you a really elegant sort of three option framework that's gonna teach you how to break the ice in a charming and spontaneous and, of course, authentic way. Because women don't wanna pick up guys. They don't want a good game. They don't want some robot who's reciting something they found on the Internet. They want a spontaneous, real, genuine, present moment with a great guy like you where sparks can just fly naturally. So let's do it. I call this authentic approach.

Connell Barrett:
When you see a woman you wanna meet, an authentic approach is something I'm about to share with you. This lets you choose from 3 icebreaking options. 3 Let's call them 3 different opening choices so that you can talk to her in a really genuine, natural way that women love. And this is by the way, this is what I teach my clients. This is what I teach my guys when we go out into the field in New York City. Once or twice a month, I go out into the New York City nightlife, and I play wingman for my guys. And this is exactly what I teach them to do. So I'm gonna give you 3 approaching options that's gonna tell you what to say so you don't have to worry about what to say.

Connell Barrett:
You'll know what to say, and you won't have to plan anything. So here we go. Here's how my authentic approach to teaching works. When you see a woman you want to approach, you open the conversation in 1 of 3 ways depending on the situation and what size you are. So option number 1 is you give her an authentic compliment. You share something specific that you like about her. Her cool tattoo, the awesome leather boots she's wearing, the confident way she's walking, you just make sure that that compliment is authentic and also g rated. That's option number 1.

Connell Barrett:
Option number 2 is you ask her a relatable question. You ask her a genuine relatable question. Ask her something you genuinely want to know given the environment or something that is a totally normal relatable thing to ask. So for example, you're in line at Starbucks. You might say to her, hey. Pardon me. Are you getting iced coffee or hot coffee? Could be as simple as that. That's a normal, relatable question to ask at the moment.

Connell Barrett:
And the 3rd option is you share an interesting observation. You call out something unusual about the situation, and this is a great way to open as well. This is your 3rd option. So you call out something unusual about her or the situation. Like, there was a time I noticed a woman holding a yoga mat in one hand while smoking a cigarette. I was in Miami. She was standing outside of a yoga studio, yoga mat in one hand, cigarette in the other. And I broke the ice by saying, ah, there's nothing like a smoke break after you crush the downward facing dog.

Connell Barrett:
Right? Because I noticed that it's a little bit unusual for a woman to be a health nut but also to be smoking. So those are the 3 options, and it's really that simple. And you get to choose the option that feels best and feels right in the moment. And choosing one of these three avenues to break the ice, this is gonna tell you what to say, and you don't have to plan it. You don't have to do what pickup guys do. You don't need to script out what you're gonna say. That robs you of being spontaneous and in the moment. That makes you sound like a robot.

Connell Barrett:
You don't wanna be some weird, fake, manipulative robot or some toxic alpha male who's using tactics to nag women, show them who's boss. That's toxic. It's gross. Doesn't work anyway. So my approach, my authentic approach, gives you 3 elegant simple options. Here they are again. Number 1, give an authentic compliment. Number 2, ask a genuine relatable question.

Connell Barrett:
Number 3, share an interesting observation. Now the benefit of this philosophy is that it's really difficult to get your approach rejected this way. I mean, think about it. Most women are gonna appreciate a sincere compliment if you mean it, or they're gonna expect a genuine normal question. Or I should say they'll answer a genuine normal question as long as it's not weird and it makes sense. So this style is as close to anything that exists in the world of dating advice that is rejection proof. Nothing is totally rejection proof, but it's as pretty close to rejection proof as you can get. So let me tell you a quick story.

Connell Barrett:
Let me tell you about the night. I first really nailed these three options and saw what great results and how great it made me feel. So back in the day, I was, like I said, I was so nervous about approaching. I was so anxious. I didn't know what to say. I was afraid I'd be weird or creepy, and I thought I'd just get rejected a lot. So I went out and I really struggled for about the first 9 months, 12 months when I first started approaching women back in the late 2000. But one night, I was at a rooftop lounge in New York City, and I had one of the best approaching nights of my life.

Connell Barrett:
I saw a beautiful brunette in a silvery dress. She looked like Jennifer Beals from the movie Flashdance. Jennifer Beals, Flashdance. She was my movie crush. I'm pretty much I'm pretty I'm pretty sure I started puberty watching Jennifer Beals dance in Flashdance. So, anyway, I walk up to this woman, and I give her an authentic compliment. I say, hey. You look just like the girl from Flashdance.

Connell Barrett:
She was my first big crush. And this woman's eyes light up, and we have a drink. We dance a little bit. A little bit later, we ended up kissing and making out on the dance floor, and I got her number for a date later that week. She ended up leaving that night with 2 friends. So she left with her friends and I'm still at the bar. A little bit later, same venue, rooftop bar. A little bit later, I turn I'm at the bar and I turn and see this really pretty petite blonde woman standing next to me at the bar waiting for a drink.

Connell Barrett:
So I just turned to her, and I went with option number 2. I asked her a question, a normal question that makes sense in the environment, which in that case, I believe I asked her, hey. What are you drinking tonight? Let me guess. You look like a Long Island iced tea girl. Right? She says, oh, no. No. I'm a tequila girl. We start talking about our favorite drinks.

Connell Barrett:
I don't remember. It's been a long time. I think I bought her a tequila shot. We had some drinks together, and I got her number as well. All I did was I went with option number 2. I asked her a genuine question that makes sense. And then as the night was winding down, I was already having a pretty great night. Right? I kissed a really pretty girl who looked like Jennifer Beals.

Connell Barrett:
Oh my god. And then I got a cute phone number from a really stylish, cool, young woman, that petite blonde woman. And then later in the night, toward the end of the night, I noticed something unusual. I see 2 women who are doing, like, martial arts poses, and they're mirroring each other in a bar, in a club. That's unusual. That's a slightly very strange thing to see in a bar. So I walk over, and I and I mirror their pose. And I said, oh, I didn't know they taught karate here, and I made, like, a karate pose.

Connell Barrett:
And they found it funny as I called out the unusual thing that I was observing. And the 3 of us talked for a while, and the 3 of us ended up leaving the bar together. No. I'm not saying it was that good. It wasn't like I was with both of them. But one of the girls, her name is Lacey, I remember I really clicked with Lacey and ended up setting up a date with Lacey, and I left the bar with these 2 women. We ended up going to another spot for a drink. So what an amazing night.

Connell Barrett:
Right? That's like that was at the time maybe the best night I had ever had out approaching girls. And the next day, my wingman, a guy named Brad, who was with me for part of the night, said, Connell, you were on fire last night. 3 different girls. Oh my god. How did you do it? How did you hit it off with all these different girls? And the answer to you, dear listener, is that I used what I now call the authentic approach method. I didn't call it that then. I'm just a guy approaching girls at a bar. But I now look back and I realize, oh, you know what I did that night? I simply chose the right approaching option that each situation presented, and that told me what to say.

Connell Barrett:
That informed me what to say. So I didn't plan anything. I didn't use any scripted weird pickup lines. I'm just being really natural, really authentic. So when you see a woman you wanna talk to, I want you to stop asking yourself the wrong question. Stop asking yourself, what do I say? What's the right thing to say? That's an understandable question, but it's not the right one to ask. A much better question is you take a look at that woman and you say, okay. That's a woman I wanna talk to.

Connell Barrett:
Which of the 3 authentic approaching openers or opening styles, which one should I choose? And you just choose one of the 3. Compliment, a question, or an observation, and that's gonna tell you what to say. You'll be able to confidently and competently approach and have a very high chance of a good conversation because these are again, I'm not saying they're a 100% rejection proof, but they're pretty, pretty close to being rejection proof. Okay. Let me walk you through some of the possible openers for all three of these natural approaching options. So option number 1, again, is to give an authentic compliment. The secret here is you notice something that you like about her, okay, besides the obvious, besides her curves, besides her body parts, and you give her a specific genuine compliment. So you wanna avoid general compliments, like, hey.

Connell Barrett:
You have a nice style, or I like your energy, or you look nice. Don't be too vague. The more specific you can be, the better, within reason. So the more specific and the more genuine, the better it's gonna go. Because women can feel when a guy's just full of shit and says something to try to talk to her. So you wanna mean what you say, whatever it is. Just like I meant it when I walked up to Jennifer Beals junior. And I told her, oh my god.

Connell Barrett:
You look like my crush from the eighties, Jennifer Beals. She could feel that I meant it, and that authentic oomph helped really sell my approach. So, anyway, here are some examples of the kinds of specific compliments that I've used. Again, I'm not giving you these to practice rehearsed examples. I'm just giving you examples to let your mind understand how it would work. So for example, I've approached and I've said these 5 things to different women over the years. Hey. I love that tattoo.

Connell Barrett:
That's a great design. Simple. Right? Or, hey. Excuse me. Those are very stylish black leather boots. Very edgy. I approached a woman once, and I said, hey. I love your glasses.

Connell Barrett:
They're very retro and cool, but also nerdy. I approached a different woman. She was at a Whole Foods. She had a nose ring that I really liked, and I said, hey. That's a great nose ring. It's very early nineties, very grungy. And then one more example would be, I was at a bookstore, and I saw a really pretty woman in the fiction section. And I said, oh, hey.

Connell Barrett:
It's nice to see that pretty girls still read actual books, especially literature. That's very impressive, I said. So I'm telling her she's pretty. I'm also saying she's smart, and I meant it too. So those are some five quick examples. And, again, you're not hitting on her. You're not hitting on her. You're just starting a conversation in a friendly way, but it's playful.

Connell Barrett:
And because you're a man and she's a woman, there's gonna be at least a little bit of flirtatious context here. We'll talk more about that in a different episode about how to make sure that you show that you are a man flirting with her. But for now, we just wanna get you comfortable approaching girls and having conversations because that's the most important part, the open and getting into a conversation. Here's a bonus tip, by the way. Again, you wanna keep these compliments g rated or PG rated at most. You can and should compliment things like her style. And it's okay to say she's pretty. There's nothing wrong with that.

Connell Barrett:
But just beware of only complimenting a woman's looks. You know? Don't just compliment her beautiful blue eyes or her gorgeous figure. Guys who do that, generally, if you are for guys who only compliment or or say good things about a woman's looks, that comes off like a cat collar. That comes off as creepy to a lot of women or just not classy. So keep it classy, San Diego. Keep it classy. And here's a mindset that I think will help you both with your confidence and also help you just go out there and get excited to take some action. I call this and this relates to the whole idea of complimenting women, giving that authentic compliment.

Connell Barrett:
I call this the $20 theory of approaching. Here's a thought experiment. Imagine I give you 5 $20 bills, and I tell you to go out into the world and find 5 people and give each person a $20 bill, wanting nothing in return from them. How would that make you feel if I gave you that mission? Now if you're like a lot of guys, you'd say, well, it's a little bit unusual, but I'd I'd feel pretty good. I'd be able to give people a 20, make their day better, and that would feel pretty good. Right? It's unusual, but it's not weird. And most people would take your 20 most likely, I would assume. Now what if I gave you a different mission to do? What if I said, I want you to go out and I want you to find 5 strangers and I want you to try to get these random people to give you a $20 bill? Try to get these people to give you $20, people you don't know.

Connell Barrett:
How would that feel? And that would feel awful. Right? You would feel like a taker. You would feel like a vagrant, a beggar. You would feel like you're just a guy who's only out for himself. It would probably feel really awful to you, and it would probably feel repellent to them. Imagine a stranger who came up to you and said, hey. I know you don't know me, but can I have $20? You would probably be like, no. Go away.

Connell Barrett:
Well, guess what? This is how the pickup guys teach good men like you to go approach girls, by making it about what you get, by trying to get something from women. And this feels awful. It feels awful to you, and it feels awful to women. So don't walk up to a woman with this idea that I must get what I want. I must get her phone number. I must get a date. I must get a result. It feels terrible.

Connell Barrett:
It's the equivalent of walking up and saying, hey. Give me $20. It just feels terrible and that's why it doesn't work. What I want you to do instead is I want you to think of yourself as just handing out twenties. You're just handing out twenties, so to speak. Twenties in the form of quick, genuine, sincere little compliments that you mean with good intention, with a good heart. It's a beautiful thing. It feels so much better.

Connell Barrett:
If you do nothing else from this episode and you just adopt this idea of the $20 theory of approaching and you just hand out twenties, so to speak, you're gonna feel so much more confident. It's gonna go so much better because you're gonna feel like a load has been lightened. You're not gonna feel like some creepy guy trying to take. You're gonna feel like a generous guy who's just handing out twenties. So that's how I want you to think about giving these authentic compliments. You're just handing out twenties. Who wouldn't take a 20? Free 20. I would take a free 20 from anybody.

Connell Barrett:
You struggle with dating. Right? Sure. You have a good job and cool friends, but you just aren't sure how to flirt. The apps don't work for you, and sometimes women put you in the friend zone. It's frustrating. Hey. I struggle with dating too. As an introvert and a total nerd, I didn't just live in the friend zone.

Connell Barrett:
I owned real estate there, but I escaped using the dating philosophy of radical authenticity, which I've used to help thousands of men in 17 countries find love. It's what I wrote about in my best selling book, Dating Sucks But You Don't, and radical authenticity is why psychology today called me the best dating coach in America. And now I wanna personally help you attract your dream girlfriend. So go to datingtransformation.com and book a free call with me. On our call, I'll tell you how my 1 on 1 coaching will help you find your dream girlfriend, and you'll be doing it by flirting with confidence and authenticity. No creepy pickup tricks needed. So go to dating transformation.com, book a free call today, and let my personalized coaching help you get a great girlfriend. Okay.

Connell Barrett:
Let's shift to number 2, the second way to elegantly, authentically approach. Number 2 is or the second option is ask a genuine question. Ask a genuine, authentic question, relatable question. K? Now the secret here is you wanna ask her a question that makes sense in the environment or given the context. So this is gonna change from place to place and context to context. This is why I don't teach canned rehearsed pickup lines. If you use a canned rehearsed pickup line, it's gonna seem weird because it's not gonna work in every place that you have that. I had a guy who was a former client. The very first intake call I did with him, he said, oh, here's how I approach women.

Connell Barrett:
I just walk up and I ask them what their favorite kind of coffee is. Well, that's great if you're at Starbucks. It's weird as hell if you're in an airplane lounge or if you're at a club on Saturday night or if you're at the gym. You're just randomly walking up asking what kind of coffee she drinks. He just didn't know what to say, so he went with that. This is a much better way to do it. So you ask a genuine question based on where you are, what you observe, and the situation. So if you're at a grocery store, your question might be, hey.

Connell Barrett:
Excuse me. What are you cooking for dinner tonight? That's a question that makes sense. If you're at a coffee shop and there there's a really attractive woman standing next to you as you wait in line for your mocha double decaffeinated half calf mocha karma karma chameleon latte, you might just look to your left and say, oh, excuse me, miss. What kind of coffee are you gonna get today? Are you gonna get iced or hot coffee? Just curious. That question makes total sense. Only the most socially stunted woman or maybe a woman who's just in a bad mood, Only a very rare woman is gonna be like, don't talk to me about coffee. That would be that that would be making her into a weird person. So, yeah, you're at a coffee shop.

Connell Barrett:
Hey. What are you gonna do with hot coffee or iced coffee today? Or here's a good way to do it. You ask her what you should get. Excuse me, miss. Can I ask you for your advice? Should I get a muffin or a brownie? What do you think? And all this I've actually used. Works really well. One woman, I even said, no pressure, but I'm putting my nutritional future in your hands, so pressure's on. And that became kind of a fun little flirty back and forth we had.

Connell Barrett:
Let's say you're at the gym. You're at the gym, you're at the drinking fountain, and your gym crush just finishes her, you know, squats, and you're both at the drinking fountain. You might say, oh, hey. What kind of workout are you doing today? Aerobic, weight training? Yeah. What are you working on today? What a normal, relatable question to ask her. It's almost rejection proof. Now what to say next, how to take it somewhere flirtatious, we'll talk about that in a separate episode. But the goal is just to get comfortable breaking the ice with women in different environments.

Connell Barrett:
And remember, because you're being radically authentic, because you're being that true best self that has value. You already have value to women. One of the biggest mistakes men make with approaching is they think their opener has to be incredible. No. You're incredible. And because you're an incredible man, your opener can just be fine, and it can work really well and get a woman into you. So don't think you need to make your opener amazing. You are already amazing, and that's what's gonna make your average opener work really well with a lot of women who like your type.

Connell Barrett:
Okay? So another example of the question, the relatable question opener. Let's say you're at a cool fun bar or lounge on Saturday night, and there's a big group of girls next to you at the bar. Again, don't ask yourself, what's the perfect thing to say? How do you open a 5 set? What did that creepy, weird pickup YouTube douchebag tell me to do? Talk to this girl and neutralize that? No. Screw all that. Just ask yourself, what's a question that makes sense to ask them? Hey, ladies. What brings you out tonight? Party? Bachelorette party? What's the occasion? That's gonna have a great that's gonna work really well because you're gonna commit to it. You're gonna believe in it, and it's a normal thing to ask. Women just wanna have a normal conversation with a normal cool guy.

Connell Barrett:
So be normal. Be authentic. That's why I go on and on so much about authenticity is women just want a regular, normal dude, an authentic dude. Here's a bonus tip about asking questions. Ask open ended questions rather than yes or no questions. Gravitate toward open ended questions, questions like why as opposed to yes or no questions. Because if you ask a yes or no question, then she might just say yes or no. You're at Tray, you're at Trader Joe's.

Connell Barrett:
Oh, hey there. Do you shop here at Trader Joe's often? If she just says yes or no, that could be the end of the conversation. Because guess what? Women get stuck in their heads too with what to say. Women struggle with this too. But if instead of a yes or no question, you ask the woman at Trader Joe's, so, why do you come to Trader Joe's? Or what's the plan for tonight's dinner? What are you shopping for for dinner tonight here at Trader Joe's? That's a more open ended question. So avoid yes or no questions if you can. Open-ended questions make it easier for her to dig a little bit deeper and have a bit more to say, which helps the conversation. One more bonus tip about this tip is I can already hear you.

Connell Barrett:
I can hear you say, hey. Wait a minute, coach. Aren't I supposed to avoid interview mode? Shouldn't I avoid questions because I don't wanna get stuck in interview mode? It's not interview mode to just ask a normal, genuine question. It's interview mode to ask 10 straight boring logical questions on a date. Don't do that. But it's normal to ask questions. One of my pet peeves, I won't mention his name, but one of my former coaches is a pickup dude, and he used to always say, make statements. Don't ask questions.

Connell Barrett:
Make statements, statements, statements. And that's just not how humans talk. People don't talk just by making statements. It's normal to ask each other questions. That's just human nature. So don't just be this weird statement making machine, nor should you be a question asking machine. Just think to yourself, it's totally fine and normal to ask a good, normal, relatable question. It shows good social skills, and it's just a normal way, it's just a confident, normal way to interact.

Connell Barrett:
And, because remember, the purpose of an approach opener is not to create amazing sparks. That can happen. Don't get me wrong. And in a separate episode, I'll talk all about more direct opens where you can say some things to help make those sparks happen. But for now, just know that the main purpose of any approach is just to start a conversation with her. That's the main way to do it. Because you have to have a conversation before you're gonna get a phone number and get a date. Okay.

Connell Barrett:
And let's go a little bit deeper on number 3 now, sharing an interesting observation. I love this one. The third option when you approach is my personal favorite because when you call out an unusual or interesting observation the right way, it can lead to a really fun, playful opener. Here's where you get to start using your sense of humor and your observational skills. And, by the way, the good news is you don't have to be the funniest guy in the room to have a funny icebreaker. You just have to notice something a little bit unusual and share that observation. That can create something really fun and funny. So let me back up a little bit.

Connell Barrett:
So there's a concept in comedy. There's a comedy writing concept called the unusual thing. The idea is that when you're watching a movie or a TV show, when something unusual enters this normal reality, the juxtaposition of the unusual thing with the otherwise normal world creates a funny situation. So, for example, a man getting his excess hair waxed, that's fairly normal. It's not that weird. But when it's Steve Carell doing it in the 40 year old virgin, and he screams out, Kelly Clarkson, and all these weird things he screams out, those weird things he screams out, that's funny because those things are unusual. Danny Pyle. Kumba Syama.

Connell Barrett:
No. Kelly Clarkson. Mhmm. He's calling out something unusual. Or let's take SNL. Maybe one of the most famous sketches is the, the more cowbell skit. Right? It's actually pretty normal. There's nothing funny about a rock band rehearsing a song.

Connell Barrett:
What makes it funny is when the manager insists more cowbells more cowbells. More and more cowbells. That's what makes it funny. That's what makes it an unusual thing. Guess what? I got a fever, and the only prescription is more cowbell. So how does this relate to what we're talking about here? When you observe something unusual involving a woman who you would love to approach, one of the third options is look for something unusual that you notice, that you can call out, and just mention it. And this can make for a very fun, playful opener. So I'll give you a couple of examples.

Connell Barrett:
A while back, I was at a bookstore, and I saw a really attractive woman, probably a tourist, who was unfolding a paper map, a big paper map. That's unusual. Who uses paper maps in the 20 twenties? I haven't seen a paper map in over a decade. So that's an unusual thing. So I approached her by saying, hey. Excuse me. I see you have a paper map. Are you a time traveler? Are you from the eighties? Is your DeLorean parked out back? Next Saturday night, we're sending you back to the future.

Connell Barrett:
And she started laughing. So I follow this thread of calling out the unusual thing and using that as a funny icebreaker, pointing out the unusual thing. K? Here's another example. I was at a coffee shop once on a Saturday afternoon, and I noticed next to me at the, like, the milk and sugar counter, I noticed this woman putting 4 or 5 packs of sugar in a giant iced coffee, just pouring in tons of sugar. That's unusual. 1 or 2 sugars is usual. 5 or 6 is unusual. So I said, oh, hey.

Connell Barrett:
I see that you take a little bit of coffee with your sugar. She chuckled and laughed. It was a really nice little light way to start our conversation. So those are a couple quick examples. Oh, and then the other example I used before. Remember, I'm I'm I see this woman with a yoga mat in one hand and a cigarette in her other hand. That's unusual. So I, yeah, made a joke about downward facing.

Connell Barrett:
Nothing like nothing like a Marlboro red after your downward facing dog. And that and just the fact that I'm calling out the unusual thing, it gives your approach there's something about there's something about calling out the truth that makes a woman a woman say, yeah. You got me. You got me. Not you got not you got her in a gotcha way. More like you're just calling out something that is truthful, but that neither of you had really noticed. Here's one more example. By the way, the observational opener doesn't always have to be funny.

Connell Barrett:
In fact, it might just be something that's unusual that is a good conversation starter. So another example from a coffee shop is I was once at a coffee shop and seated at the coffee shop was a woman, and she had a big sticker on her laptop of the band They Might Be Giants. I'm a They Might Be Giants fan from going way back, one of my favorite bands. So I simply noticed that that's unusual. It's unusual for me to notice that kind of thing, a band, a sticker of that band. That's a little bit unusual. So I just said, hey. Wow.

Connell Barrett:
I love your They Might Be Giants sticker. That's so cool. And her eyes lit up and she smiled. She said, yeah. I love them. And I said, oh, what's your favorite song? We talked about our favorite They Might Be Giants songs. So that wasn't a funny opener. Think of being funny and playful as a bonus when you notice something unusual, but it's not required.

Connell Barrett:
And, by the way, one final point about the third option, observing something unusual, is that it's not always gonna happen. You're not always gonna find something unusual to observe and call out, so don't expect that to happen. I typically lean on my clients and I typically lean on the first two options, the authentic compliment, which you can always find something about her that you'd like, or a question that makes sense. The observation is something that will happen so it'll arise often, but not every time, so don't feel like you have to force it. That's sort of one to just notice when you notice it. Okay. Let's take a really quick break. We'll be right back.

Connell Barrett:
Don't fast forward. This is not an ad. It's a free thing that's gonna help you flirt with confidence because I'll bet that you struggle with what to say to women and how to flirt. Right? Well, let's fix that. I'm gonna give you what I call the flirty thirty. These are 30 flirty questions to ask women on the apps or on dates or when you approach so that you can confidently connect with cool sexy women starting today. It's time to stop running out of things to say and start asking them flirty questions that are gonna make them want to date you. So to get your copy of the flirty 30, it's totally free.

Connell Barrett:
Just go to dating transformation.com/flirty30. And that's flirty30. Datingtransformation.com/flirty30. You're about to start confidently flirting with women, going on dates, and soon getting a great girlfriend. Go get your flirty 30. Okay. And we're back. Okay.

Connell Barrett:
Here's a quick thought experiment. I want you to imagine a stylish, attractive woman sitting in a cafe because what I'm gonna do is give you a situation, a scenario, and we're gonna run through how these three authentic, approaching styles could play out. So imagine a really attractive woman. I'll paint a picture for you. She's in the cafe. She's drinking an iced coffee. She's got a cat tattoo on her right bicep. She's reading a book.

Connell Barrett:
She's reading an actual physical book, a Stephen King book. There you go. Here's our scenario. Now here's the old way. Here's the wrong way to approach her that you've probably been going about it this way. The old way is let me try to think of something perfect and funny and witty that'll create instant attraction and not get me rejected, but, of course, you probably can't think of anything like that, so you don't even talk to her. Or the other old way is you have some prepared canned line that you got from some jackass on YouTube who doesn't know what he's talking about, and you just sound robotic, and that's no good either. That's the old way.

Connell Barrett:
Here's the new way. The new way is what you and I have been talking about. The new way is that you use the authentic approaching kind of framework that I've been talking about. And, basically, what this means is that you are in touch with your worth. You're more than enough. A lot of women are gonna like you just because you have value. What you say doesn't have to be amazing. You are already amazing.

Connell Barrett:
What you say is just an extension of who you are. So then you look at her and you decide to give her an authentic compliment. You might say, excuse me, miss. That's a really cool cat tattoo. I like the design, and I like the colors that you chose. And she responds really well to this because guess what? She put a lot of time into that tattoo. She thought about it. She planned it.

Connell Barrett:
She went and paid for it. And she can also feel that you're being genuine. And you're also complimenting her about something that's really important to her. So she likes the fact that you're not hitting on her. Sure. You might be interested, but you're not staring at her body. You're not saying something vulgar. You're talking about her cat tattoo.

Connell Barrett:
So you're breaking the ice in a warm, real way. Now let's try the same. Let's approach the same woman. Let's use number 2, asking a genuine question. Let's say you notice she's drinking. What was it? Iced coffee, I said? Let's say she's drinking an iced coffee. You say, hey. Excuse me. I see that you're drinking an iced coffee. Are you normally an iced coffee drinker, or do you ever drink hot coffee? Just curious.

Connell Barrett:
So simple. Right? Look. I'm not saying this is amazing. I'm not saying this is the world's greatest content. It doesn't have to be. You just start a conversation in a normal, relatable way. And by the way, what's more normal and less creepy than talking about coffee in a coffee shop? So that's number 2, asking a genuine question. And let's go with number 3, sharing an interesting observation.

Connell Barrett:
Let's say that you noticed the Stephen King book. Okay? And I'm recording this here in November. Spooky season's over. It's not really the time of year. It's getting into the holidays now. Let's say that you noticed this woman reading her Stephen King book, and you'd think that's a little bit unusual because the spooky season's over. It's also kind of unusual that somebody reads an actual physical book. Like, who the hell reads actual physical books? That's more and more unusual.

Connell Barrett:
So you might walk over to her and say, hey. Pardon me. I see that you're actually reading a real book. That's so cool. It's nice that you're very old school. I love that. And you might crack a joke based on the idea of her liking old school things. Do you use a VCR? Do you drive a 57 Chevy? You could do that.

Connell Barrett:
Or maybe you go with the idea that she's reading a horror book. She's into the spooky season even though it's not a spooky season anymore. You might say, hey. I noticed that you're reading a Stephen King book, and it's not even Halloween anymore. And she might say, oh, yeah. Well, I like scary stuff no matter what the time of year is. So you might say, oh, well, interesting. Do you open your Christmas presents in January? You could play a little game.

Connell Barrett:
Like, if this unusual thing is true that she likes scary books after the spooky season, maybe she likes Christmas presents in February, or maybe she hunts for Easter eggs in July. You could say you could follow that line of playful, banter. So, yeah, those are examples of kinda running one approach through these three different ways of doing it. The bottom line is the authentic organic style of approach that we've been talking about, it just feels so much better to women. And it feels good to you because not only is it not creepy, but you actually have the chance to give a woman a rom com movie moment. Because think about it. If you're the 400th guy who swiped right on a woman's Tinder or Hinge profile that week, she's not even gonna notice you. But if you're that one charming, authentic gentleman who had the courage and confidence to break the ice in the real world at the coffee shop or in the frozen food section, you chatted in a light way, and you just allowed your natural chemistry to win her over, she's gonna text her girlfriends.

Connell Barrett:
She's gonna say, oh my god. I just met the coolest, most charming guy. We started talking. I'm just standing there shopping for frozen peas in the grocery store. And next thing I knew, I'm chatting with him. I'm giving him my number. It was like something out of a movie. And then if you end up dating this woman and she becomes your girlfriend, guess what? For the rest of your relationship, every time somebody asks the 2 of you, so how did you 2 meet? Which you will be asked 100 times, I promise you that, by your friends and people you meet.

Connell Barrett:
She is gonna smile, and she's gonna be able to say, well, it's actually a great story. He just came right up to me, and he asked me if he complimented me about my, my really cool Chuck Taylors I was wearing. And we started talking about clothes and sneakers, and next thing I know, I'm giving him my number, and we were on a date. It was he who I thought was so impressed. It was like a movie. So, anyway, this works. This is exactly what women want, and it's a great way to know exactly what to say without planning what you're gonna say. I know it's a little scary.

Connell Barrett:
You like to know what you're gonna say. Let go of that. Embrace uncertainty. Embrace spontaneity. This is how we give women those magical moments that they love and that have become so, so rare in our Tinder and online dating world. So, yeah, give her that gift of meeting a great guy, the authentic, awesome you. Okay. Here's a bonus tip.

Connell Barrett:
I like putting a little cherry on top at the end of every episode. Here's one more bonus tip. Here's a quick tip on how to never run out of things to say. I want you to follow the simple rule. This idea of whatever I'm thinking and feeling is what I'm saying and doing. A simple philosophy. Literally speak your thoughts. If you're not sure what to say to a woman, then say exactly what you're thinking even if you don't know what to say.

Connell Barrett:
Here's a quick client success story. I have a client I used to work with, a great guy named Taylor. Taylor is a very successful person in the entertainment world out in California. And Taylor and I worked together, and he was so in his head I didn't know what to say when I approached. What should I do? What should I say? What should I say? What should I say? And he was so worried about saying the right thing. And I took him out one night and I said, I just want you to literally say whatever's on your mind. And what was on his mind that night mostly was, hi. I'm Taylor and I don't know what to say to you.

Connell Barrett:
So I said, guess what? That's gonna be your opener tonight. So he did, like, literally two approaches. He walks over to a really cute girl. 2 two female friends were hanging out. He walks over to the girl he's into, and I said, there's your opener. Go do it. He walks over and says, hey. Hi.

Connell Barrett:
I just saw you, and I don't know what to say. And she smiles. She said, what? Whatever. How are you? How's your night? And he started laughing and talking. And then he relaxed because he was in the conversation. And 5 minutes, maybe 10 minutes later, they were making out at this bar. This is, like, on a Friday night, midnight. Right? They're making out at a bar.

Connell Barrett:
His opener was, hi. I don't know what to say to you. I'm Taylor. That was his opener. Nothing fancy. She barely even heard what he said. Here's what she noticed though. She noticed that this genuine, cool, charming guy was walking up, being sociable, being raw, being himself, being real with good intentions, and next thing you know, they're having a steamy bar make out.

Connell Barrett:
So anyway, your mission I'm sorry. Your lesson here is to follow this idea of literally speaking your thoughts. If you're in your head because pretty girls make you nervous, look at her and say, oh, hey, sorry. Pretty girls make me nervous. I get nervous sometimes. Oh my God. That kind of vulnerability? That's like Hugh Grant romcom movie adorableness. Women love that.

Connell Barrett:
Women love that. Okay. Here's your mission for this episode. Remember, pretty much every episode ends with me giving you a mission to do in the real world because you don't wanna just consume information. You wanna go out and take action. Information is overrated. Action is underrated. So here's your mission this week to go take action.

Connell Barrett:
I want you to go out 3 times this coming weekend, and I want you to approach 3 women. And I want you to simply apply these three ideas. Then I should say choose one of the three ways I've given you to approach women and break the ice. So three times this weekend, I want you to see a woman who you wanna talk to, a woman whom you don't know but you find is attractive and intriguing, and walk up to her and size up the situation and either, 1, give her a genuine specific compliment that's g rated, or 2, ask her a question that makes sense based on where you are and what's happening in the environment. And option 3 is to observe something unusual about her or what's going on and use that. That is your mission. Okay? Yeah. So we have one more really amazing special episode in this week's 5 part series all about how to help you get a great girlfriend, get on that path to finding a great girlfriend.

Connell Barrett:
This was episode 4. Coming up is a very special episode. It's special because I'm gonna be cohosting the episode with my girlfriend, Jessamine. My girlfriend, Jess, is gonna join me in the next episode. We're gonna talk all about our first date because now you know all about the power of being radically authentic. You know how to flirt with women using man to woman communication. You know how to get some dates and some success on dating apps with openers. You know how to text women.

Connell Barrett:
You know how to approach and how to break the ice and have some dating leads through all the different ways you can get some dates. Now for the how to get a girlfriend podcast, I thought it made sense to have my girlfriend on and say, hey, babe. How did I get you? How did I attract you? So in the next episode, you're gonna meet my amazing girlfriend, Jessamine. We're gonna talk all about how she and I first met, how we connected, and the things I did well and maybe some things I didn't do well on our first date. And she's also gonna give you so much great insight about what a quality, beautiful, wonderful woman is looking for in a man and some great tips and do's and don'ts on first dates. So please check out the next episode. I'm so excited to talk with my girlfriend, Jess. She's my schmoopy.

Connell Barrett:
I love her. Okay. If you liked this episode, please leave me a review or share the episode with a guy who needs a little dating help. If you didn't like this episode, I can take it. Give me some feedback. Tell me what I can do better. I just wanna serve you. I think of myself as your coach.

Connell Barrett:
I am your hitch here on the podcast, and I just wanna help you. So any feedback from you to me, I'm happy to listen to. And remember, your dream girlfriend, she's out there, and she is gonna love you. But she has to meet the real authentic you. So go out there, take authentic actions, carpe datum. Seize the date. Till next time.

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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.

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NYC Dating Coach Connell Barrett

106 W 32nd St, New York, NY 10001

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