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7 Make-or-Break Dating Moments to Either Win Her Interest… Or Lose It

Featuring NYC Dating Coach Connell Barrett

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There are pivotal moments in dating that determine whether you create romantic sparks with a woman or lose your chance with her entirely. In this episode of “How to Get a Girlfriend,” dating coach and bestselling author Connell Barrett breaks down 7 make-or-break moments that will determine when and if you find the relationship you want.

Episode Highlights:

02:45: Make-or-Break Moment 1: To Approach or Not to Approach?

07:30: Make-or-Break Moment 2: When and How to Ask Her Out

12:15: Make-or-Break Moment 3: THIS Makes Her Swipe Right

16:45: Make-or Break Moment 4: Use Your First-Date Superpower to Escape the Friend Zone

23:20: Make-or-Break Moment 5: The Secret to Pre-Date Texting

26:05: Make-or-Break Moment 6: How to Pass Her Tests

30:10: Make or Break Moment 7: A Texting Move to Stop Getting Ghosted

BOOK A FREE CONSULTATION WITH CONNELL TO SEE IF DATING COACHING IS RIGHT FOR YOU: DatingTransformation.com

Episode Transcript

Connell Barrett [00:00:00]:

To approach or not to approach, that is the question. Shakespeare should have written about dating. Welcome back to the How to Get a Girlfriend podcast. I’m your host and dating coach, Connell Barrett, helping you attract incredible women and getting a great partner, a great girlfriend, and doing it with authenticity. No sketchy, weird pickup artist moves needed. I’m so excited today. I have a really fun episode. If you hear jingling in the background, by the way, I am a new cat dad.

 

Connell Barrett [00:00:36]:

I have these two little orange tabbies who are literally running around my apartment, my studio slash apartment, playing with cat toys. So if you hear a little bell going off, you’re hearing my two little orange boys. Today’s episode, I want to talk about make or break moments. Moments of truth, make-or-break moments that determine whether or not you and that woman end up as a couple, or at least end up having some kind of romantic connection, a win-win where you’re both into each other. You date for a while, you hook up, you fall in love. There are make-or-break moments that happen early in the dating and courtship process that determine your success. They’re subtle. Often they’re very subtle.

 

Connell Barrett [00:01:24]:

Sometimes they’re literally invisible. And I just want you to be aware of them. Here are 7 of the most common make-or-break moments. I’m going to run you through each one. We’ve got approaching, we’ve got online dating, we’ve got flirting, and how to handle yourself on a date. Let me start with a story though. I want to talk about the first make-or-break moment, which is the moment you decide you either will or won’t approach that woman. I remember many years ago, I’m in a Starbucks on Park Avenue, 29th Street, New York City, on a Sunday afternoon.

 

Connell Barrett [00:02:05]:

I had never approached a woman before, but that day I saw this really pretty brunette sitting by herself. She’s on her phone. I remember she looked like Katie Holmes, who was my crush at the time. She was my late 2000s crush. And I walked over to her seat, her table, and I wanted to approach her, but I didn’t. I literally just walked around her table a couple times trying to think of the right thing to say, not coming up with anything good enough. And I went and sat down thinking, okay, let me try again. I was worried about other people seeing me and wondering how bad it might feel if I bothered her and creeped her out.

 

Connell Barrett [00:02:59]:

And I was also just worried that I would say the wrong thing and she wouldn’t want to talk to me and that would make me feel shitty. So I sit back down, I’m trying to think of something better to say. And 5 or 10 minutes later, she walks up, leaves. And I remember thinking, gosh, if I could have only gone and approached her, I might be on a date with her tomorrow. I might have her in my life. But I don’t now. She’s going off to meet some other guy, probably, and it won’t be me. So these are high stakes moments.

 

Connell Barrett [00:03:29]:

These are make or break moments that determine whether or not you find love. That’s why I’m going into these. They’re important. So make or break moment number 1 is deciding to approach or not to approach. To approach or not to approach. That is the question Shakespeare should have written about dating. And there are probably hundreds of times a year, dozens of times a month when you see a woman you would love to talk to, but you don’t do it. And that’s the make or break moment.

 

Connell Barrett [00:04:02]:

So here’s a quick story of me, of me doing the right thing, because I want— I shared that failure of mine at Starbucks. I want to share a success. Fast forward a few years. I’ve got a lot of approaches under my belt. I’m not yet a dating coach, but I’m getting pretty good at this. And I saw a woman out in a park here in New York City. And I actually had just wanted to but failed to approach a different woman, and I was so mad at myself. I said, oh, Connell, damn it, you are going to approach the next most attractive, the next cute girl you see.

 

Connell Barrett [00:04:43]:

And I see walking across the street in the shadow of the Flatiron Building here in New York City, I see this cute curvy woman. She was wearing a pencil skirt. She had a fedora on. And I remember I was listening to a Frank Sinatra song on my phone, and I saw this woman. I thought, oh my gosh, this was meant to be. She’s got a fedora on. I’m listening to Frank. This was meant to be.

 

Connell Barrett [00:05:07]:

So I was nervous, but I made a decision. I said, let’s go. Let’s go talk to her. I walked up to her, and I even had something ready to say. I was going to say something about, hey, I like your fedora. I’m actually listening to a Frank Sinatra song. That might have worked well. I get up to her and a catcalling dude on the street shouts out at her.

 

Connell Barrett [00:05:33]:

Like, I’m literally 3 feet away from her. A catcalling dude says, yells toward her, “Hey baby, I like the way you walk.” And I heard that. I made eye contact with her. She understood what was happening here. And I walked over and said, hey, I just want to apologize for my dad. He does not know how to talk to, to women, just in the moment, right? And she threw her head back, laughed. She was— and she said, you’re way better at hitting on girls than he is. And she was smiling ear to ear.

 

Connell Barrett [00:06:10]:

We stood and talked for about 10 minutes. And we were on a date 2 nights later. 2 nights later, we went to an improv show on our first date and had a great time, and we ended up becoming boyfriend-girlfriend. Her name is Catherine. Hi, Catherine, if you’re listening. And what an amazing moment that was for me. That was powerful for me because I realized— the big truth I realized was that you might think that you, quote, can’t approach a woman because it’s uncomfortable. You can..

 

Connell Barrett [00:06:41]:

You simply decide to. You make an adult decision using good old-fashioned courage. I was actually pretty nervous as I walked up to her, but I did it anyway. And I could have approached that girl at Starbucks a few years earlier, but I chose not to. And that’s the takeaway I want to give you with this first make-or-break moment is you can decide to approach any woman you want to at any time. You can’t decide it’s going to feel good.. You can’t decide you won’t be nervous. You can’t— certainly can’t know for sure that it will turn into a phone number or a date.

 

Connell Barrett [00:07:15]:

But that’s a make-or-break moment, and you’re in control of it. Okay, you can decide to talk to any woman you want to. And had I not walked up to Kat that day, I would have lost out on this really great, sweet, warm, beautiful young woman who became my girlfriend for about 6 months. So that was a make or break moment. So yeah, takeaway for you is look for those make or break approaching moments and decide to do it even if you’re uncomfortable. Okay. Make or break moment number 2 is also about approaching. Here’s a quick story.

 

Connell Barrett [00:07:52]:

Fast forward a few more years. I’m now a professional dating coach. It’s in the mid-teens and I’m in a park in New York City. With a couple of clients. One of the things I do with my clients is we go out and approach girls together. And I’m out with two clients, Joel and Chris, I believe was the second fellow’s name. But I remembered the Joel story. So I’m giving Joel and Chris approaching instructions, go talk to her, go say this.

 

Connell Barrett [00:08:23]:

And Joel walks over to a really pretty woman. They’re sitting on the bench, the conversation’s going really well. She’s smiling, she’s laughing. It couldn’t be going better. I realize that Joel doesn’t seem to need me. So I leave the scene for a couple minutes. I go find Chris. I come back about 10 minutes later.

 

Connell Barrett [00:08:41]:

And that young lady is sitting by herself, really pretty brunette, sunglasses on, just sitting in a park reading a book, I think. And I’m like, okay, that ended. Let’s— I wonder what happened. I look around for Joel. And I see this bench about 50 yards away, are around this little curve in the park. This is Madison Square Park, by the way. And I look around and I see Joel sitting by himself and his face is in his hands. He’s clearly having some kind of little mini crisis.

 

Connell Barrett [00:09:11]:

And I’m thinking, oh my God, what happened? What did she say? What did she do? Did she call the cops? Did she tell him to get away? Did she call him names? I walk over to Joel and I say, dude, what happened? He said, “Oh, I screwed up. I’m such an idiot.” I said, “What happened?” He said, “Well, conversation was going great. And I wanted to ask her out. But I just didn’t. I just said, ‘Well, nice meeting you.’ And then I walked away. And I’m so stupid. I’m such a chicken.” And I gave him a little pat on the back. Literally, I think.

 

Connell Barrett [00:09:49]:

And I said, okay, we’ll talk about this later, but before— we’ll break this down later. She’s sitting right over there. And I said to him, I asked him a simple question that I think is a really powerful question. I said, if you knew you could not fail, and by walking back over there, what would you say? If you knew you couldn’t fail? He stood up, he got a little bit of hope in his eyes and a little bit of determination. He said, you know what, if I couldn’t fail, I’d walk over there. And I’d say to her, I forget her name. Let’s say it was Alice. I’d say to her, Alice, I wanted to ask you out a few minutes ago.

 

Connell Barrett [00:10:29]:

But I wimped out because you’re so pretty. But I had to come back and ask you if you want to go on a date. And I said, boom, there you go. Go over and say those exact words because those words are true. They’re genuine, they’re authentic. So he walks over with a head of steam and I’m about 50 yards behind him. I couldn’t hear because too far away, but I could see it. So it played out for like a, like a silent movie.

 

Connell Barrett [00:10:56]:

Cause I couldn’t hear, I couldn’t hear the audio. He walks over, he stands up, he stands above her. She looks back up, smiles because, oh yeah, Joel, the guy I was just talking to. And I hear him say the thing. I’m sorry. I see him say the thing. I couldn’t hear it. And I watch her face break out into a big, big, big grin.

 

Connell Barrett [00:11:19]:

And she puts her hand out as if to say, give me your phone. And she takes his phone and puts her numbers, puts her number in the phone and they set up a date. So the make or break moment I’m talking about here, is once you start approaching women, once you finally start to do it, there’s going to be a second moment of truth, a second make or break moment, which is make— just making that choice to play to win and not settle for a good conversation. Make sure you ask for the date. Joel was settling for a good conversation. And that lower self, that voice of self-doubt, will say to you, oh my gosh, I’m approaching a girl and it’s actually going pretty good. I don’t want to ruin this good feeling, so I am going to just settle for a nice conversation. But if you do that, you’re going to lose the chance of even meeting that woman.

 

Connell Barrett [00:12:19]:

Why are we doing this? In large parts, you can find love, get dates. So learn from Joel. It’s going to feel so much better if you just Go for the phone number, go for the date. By the way, there are times when you’re not— when you’re going to go for a number, go for a date, and she won’t be interested, or she’ll have a boyfriend. That’s fine too. You might be surprised how good you feel when you just speak the truth. Cool. All right, let’s go to make or break moment number 3.

 

Connell Barrett [00:12:53]:

This one, let’s switch to the, to the dating apps. I call this the online dating profile deal breaker. Here’s the make or break moment. The make or break moment is, is she’s on your profile and you probably think that it’s all about the photos. If you have good photos, you’ll succeed. If your photos aren’t good, you’ll fail. And that’s not quite true. Really good, attractive photos that show your interesting, normal, authentic life.

 

Connell Barrett [00:13:29]:

That will get a woman swiping through the rest of your profile. But the make or break moment is when she then looks at your bio and your prompts and she says, oh yeah, this guy’s my type, or this guy made me laugh. There’s some personality, there’s some humor, there’s some realness that says to her, this is my kind of guy, or at least at the very least says to her, says to her, a date with him would be fun. So that’s the make or break moment. It’s what a woman experiences while looking at your profile. I’ve had a lot of women say to me and my clients on dates, they’ve said things like, you know why I’m on a date with you? You made me laugh on your profile. That just got me giggling. The thing you wrote about X or Y, the joke.

 

Connell Barrett [00:14:23]:

Or they said things like, oh, I like your photos. But what really made me want to meet you was I just wanted a date with a guy who likes some of the things I like— musical theater. I’m a theater nerd, by the way. So I’ve had a few dates with women over the years who are into theater, into the arts. So your make or break moment, the make or break moment is the moment you give women on your profile. So you’re going to want to make sure, of course, you want to have good photos. That’s absolutely essential. At the same time, you’re also going to want at least one prompt that makes a woman laugh, literally makes her laugh out loud.

 

Connell Barrett [00:15:03]:

And also one part of your bio that conveys a clear, specific glimpse into who you are as a man so she can understand what kind of guy is this. And in terms of a funny prompt, the one that has worked really well for me lately is— this is on my Hinge and my Bumble right now. It says, if you like tall, handsome, charming, funny, financially secure, humble, successful men who love dogs and kids, dot, dot, dot, then you should be my brother. A lot of women laugh at that, and they— I get a lot of messages saying, hey, I really want to meet your brother, Connell. Is he free? And I might say, ah, sorry, my brother is happily married, but I’m available. And there’s something about making a woman laugh that gets the matches, and that gets her to swipe right on you and really consider a date with you. So remember, good photos will get her looking at your profile. Bad— by the way, bad photos will get women swiping left in less than 2 seconds.

 

Connell Barrett [00:16:12]:

Good photos will get her swiping through your profile. What will seal the deal is one piece of your bio that makes her laugh because your authentic sense of humor is coming out, and also that she gets a sense for who you are as a guy. Okay, make or break moment number 4. Let’s go to the first date. Turning things from friendly to flirty, or making sure the date is, is more than just friendly, it’s flirtatious. In other words, making it what I call man-to-woman communication. You know that you have to flirt, right? But you might not be doing it. You might be playing it safe.

 

Connell Barrett [00:16:59]:

And I want to share a story about my client Trevor. Trevor, this is in my book. It’s a pretty good story. So Trevor came to me because he was in the friend zone. And Trevor had like literally 6, 7, 8 dates in a row where he heard almost verbatim, hey, you seem like a great guy. I’m just not feeling it from, from women after first dates, like 9 out of 10 times he was hearing that or something like that. And so he and I started working together. And I gave him sort of the way to, the way to flirt on a first date.

 

Connell Barrett [00:17:38]:

And the vibe, the channel, I call the flirting sort of context or frame. I call it man-to-woman communication. And you might think that flirting is just about giving a woman one compliment. Or that if you just make good conversation, good friendly conversation on a date, that hopefully will be enough because she likes you for you. It might not. It really might not. And it wasn’t for Trevor. Trevor was being funny.

 

Connell Barrett [00:18:08]:

He actually is funny, but he wasn’t being what I call man-to-woman. Let me pull back for a second and share this. There are only 3 social channels to communicate on which to communicate with women. Here are the 3 channels. Every single conversation you have with a woman falls into one of 3 channels. One channel is friend-to-friend, the way you talk to friends. The second channel is business/transactional, you know, the way you communicate at work or in a transactional business setting. Like the, the waitress is coming over, she’s talking about the food order, she’s not talking personally with you, probably.

 

Connell Barrett [00:18:49]:

And the third channel is man-to-woman communication. So if you are ever struggling with not getting second dates, if you’re in the quote-unquote friend zone, it’s very likely because you are talking in a more friendly way and/or transactional, logical way, not in a man-to-woman way. And that’s what Trevor was doing wrong. So I gave Trevor some marching orders. He has a first date with a woman named Becca. Becca is a chef here in New York City. And she had had several dates with guys that didn’t go well. She basically was putting guys in the friend zone left and right.

 

Connell Barrett [00:19:27]:

She didn’t want to, she just wasn’t feeling what women need to feel. As I watch my orange tabby do backflips. Anyway, so Becca and Trevor go on the first date. And there’s some really important couple make or break moments. There was a make or break moment early on. One of the tips I gave him for being man to woman is as men, it’s our jobs to lead a date to a good place. It’s like leading a dance. And early on in the date, there was a point where she was telling a fairly long story that just wasn’t really helping the date, like a 2 or 3 or 4 minute story.

 

Connell Barrett [00:20:08]:

About, I don’t know, shopping, kind of a girly, a girl woman topic. There’s nothing wrong with those topics. But he listened for 2 or 3 or 4 minutes and realized, oh my gosh, I’m not being honest with her. This story is boring. So he felt nervous about this. But he basically, he jumped in and interrupted her and said with a smile on his face, he said, hey, I gotta be honest with you. I’ve I totally lost interest in that story. I almost fell asleep.

 

Connell Barrett [00:20:38]:

But listen to what happened to me today. And he tells a story about something that happened to him that day. He told me that she gave him this look. She cocked her head and gave him a look as if to say, did you just shush me and take over the conversation? But the thing is, the crazy thing is, is she was doing it more— the look was a sense of respect, not how dare you interrupt me. Now, by the way, the lesson here is not to interrupt women and cut them off. That is not the lesson. No bueno. That’s not what I teach.

 

Connell Barrett [00:21:18]:

However, the reason that worked with Becca, and it did work, was that she basically said, okay, finally a guy who’s not afraid to tell the truth to me, who’s not afraid to take a risk, a social risk for the betterment of the date. He also did other good things on the date. He was a little bit teasing, a little bit snarky, and also very sincere and genuine. And he let her know when the time was right that he thought she was really sexy and cute. So he was turning up these man-to-woman dials. By the end of their date, Becca was sitting on Trevor’s lap. They were kissing, making out. This is at a bar.

 

Connell Barrett [00:22:02]:

Excuse me. This is at a, as I understand it, like a kind of a small corner candlelit bar, corner bar in a neighborhood in New York City. This is, this is not like a club at 1 AM on a Saturday. It’s like date night on a Thursday night. They’re making out, she’s sitting on his lap, and then she asks him out for the second date. And their second date was a couples massage. Just so happened she had a coupon or some kind of credit for a couple’s massage, and she said, you know what we should do for our second date? She’s sitting on his lap, and he, and he said, sure, sounds good. And their second date was a, um, a romantic couple’s massage.

 

Connell Barrett [00:22:44]:

I couldn’t make this shit up. So the main takeaway I want you to have from this is your job on a date is to show up authentically, to be present, to be yourself. It’s also to lead and to get on that man-to-woman wavelength. If you get on that man-to-woman wavelength, then you’re not going to get in the friend zone very often, maybe never. And you’re going to have some really great dates with women. I can’t promise you you’re going to have a romantic, R-rated couples massage for a second date. But, but actually, if you work with me, you might. Uh, okay, let’s go to make or break moment number 5.

 

Connell Barrett [00:23:28]:

Let’s talk about make or break moment number 5, do or die moment: keeping the text momentum going between dates. This can cost you a date, sadly. I have a good buddy, my client friend Nick. Nick recently matched with a woman on Bumble Classic match situation, bread and butter. He’s doing everything perfectly. Got the date set up, got off of the app, off of Bumble, set up the date for about 6 days away. That was the day they were both free. Let’s say that’s on a Sunday and their date’s on Friday night.

 

Connell Barrett [00:24:06]:

Okay, he goes quiet, no texting. He does not text her the rest of Sunday, Monday, Tuesday, Wednesday, or Thursday. Their date is Friday night. He doesn’t text her at all. And come Friday morning or late morning, he shoots her a text and says, just says, hey, just checking to make sure we’re still on for tonight. And she writes him back. Honestly, she said, to be honest, I’ve lost interest. I didn’t hear from you.

 

Connell Barrett [00:24:34]:

And you don’t seem like you’re that into this. So I made other plans for tonight. Sorry. And she was well within her rights to say that. I’m on her side here. And it was a really valuable lesson for Nick to keep the text cadence going. It’s a make or break moment. It’s once you, once you, you and she agree to the date, you don’t know for sure she won’t flake.

 

Connell Barrett [00:25:00]:

And flaking is usually not the woman’s fault. It’s usually a result of the mistake the man makes. By going quiet, either texting poorly or not texting at all. So you want to keep a cadence going during dates. It’s not enough to just set up a date. Most women like at least a little bit of messaging leading up to a date, on bare minimum, just to keep a social connection going, bare minimum, which he wasn’t doing. As an added bonus, what I love doing with my clients is helping them not just keep the texting momentum going between date— between setting up the date and date number 1, but to dial up attraction. I love sending a message the day before a date, you know, hey Rebecca, I got a brand new haircut, so I’m gonna look extra handsome tomorrow night.

 

Connell Barrett [00:25:57]:

You better bring your A-game. You know, something little fun, flirty, playful messages like that can, can get women excited. Not only not cancel on you, but actually get excited about the date. I like to look at the text leading up to a date as movie trailers designed to get her excited, get both of you excited, and the date is the main feature. So that’s a make or break moment. Very subtle. Don’t go quiet. And the same— it’s not just about between setting up the date and date number 1.

 

Connell Barrett [00:26:29]:

Same goes for date number 1, between date number 1 and date number 2, same thing can happen. So keep it— keep a texting cadence going, at least 1 message every day or 2. All right, let’s go to make or break moment number 6, which is how to handle a woman’s tests. Different women, most women on some level are trying to gauge your, for lack of a better term, your integrity. You’re not integrity as a man, but your strength, your, your solidity, your value, your strength as a man. And so there’s a term in the world of dating gurus, you may or may not know this term, it’s called shit test. A lot of women give guys, quote, shit tests. That’s not a bad thing.

 

Connell Barrett [00:27:17]:

It’s actually something women have to do. That’s the other term I learned back in the day was congruence tests, meaning she wants to find out if you are congruent and as, as confident and cool in reality as you are projecting, that those two things are aligned and congruent. Let’s call them shit tests. A shit test is just a woman’s way of finding out, okay, is this guy, is this guy man enough for me? Is he man enough for me? And so you want to be aware that shit tests might happen with someone, from some women. And don’t think of it as a bad thing. Think of it as an opportunity, because you pass the test, then she’s going to become more into you. Here’s an example of a shit test. It can be small.

 

Connell Barrett [00:28:04]:

A shit test— my future, my then first date, future girlfriend Lorraine, We had a first date and we were talking about Will Ferrell movies and we were talking about SNL. And she said, so what do you think about Will Ferrell? Do you think he’s really overrated? She— it’s like she was trying to lead me down that path to see if I would say that. And I said, no, I think he’s amazing. He’s comedy genius. I love Will Ferrell. Old school, hilarious. And she said, yeah, I love him too. She was trying to see if I was going to say what I thought she wanted to hear.

 

Connell Barrett [00:28:44]:

That would have been a mistake. That’s a little make or break moment where you can lose a woman by saying the thing, by doing a— by contorting yourself into the position of what you think she wants to hear and see, as opposed to just being genuine. Part of why my religion, my philosophy is authenticity is if you know who you are, what you stand for, what you believe, you don’t have to worry about that. You just lead with the truth. And by the way, it— maybe I didn’t like Will Ferrell. That’d be fine too. I would have told that truth, but Will Ferrell’s great. My mistake would have been had I said, oh no, I love Will Ferrell.

 

Connell Barrett [00:29:24]:

He’s fantastic. When I didn’t believe it or vice versa. So understand that women are looking for chinks in the confidence armor, and they have to do this because she wants to end up with the most incredibly strong, confident guy. So of course she’s going to test you. Not every woman. Don’t get in your head about this. Don’t be defensive. Don’t think of it as women are trying to test us.

 

Connell Barrett [00:29:47]:

We’re all trying to find a really great partner. We all are. And we all have our own screening system for what we want. That’s all it is. It’s just part of the screening system of many women. By the way, many women do not think about testing guys at all. So case-by-case basis, but be ready for it because when it does happen, if you fail the quote-unquote test, then you could lose that girl. And if you pass it, she’s gonna be more into you because she’s gonna realize, yeah, this guy is who he says he is.

 

Connell Barrett [00:30:18]:

Okay, let’s do one more. Um, this is a good one. I like this one. Here’s make or break moment number 7: whether or not you follow up to an unanswered text message. So you send that text, right? Do you go quiet or do you follow up in a charming way? That’s a huge make or break moment. It’s so subtle, but it can make the difference between her going on a date with you, intimacy happening, love possibly happening, it can make all the difference. So that’s the moment, the moment to be aware of. You send that text message, you wait 1, maybe 2 days, no response.

 

Connell Barrett [00:31:03]:

The mistake would be if you just gave up and made an assumption that she’s just not into you. Here’s a huge misconception I want to clear up for you. You might think that an unanswered text message means she’s not into you. It does not. It just means she didn’t see it, or she saw it and didn’t have time to respond. Or worst-case scenario, she saw it and she wants to see if you are persistent. Basically, it’s a, it’s a more passive test. Make or break, right? Test number 6, make or break number 6, testing her, testing you.

 

Connell Barrett [00:31:45]:

So yeah, the core truth is, here’s where you probably are right now. You send the text message, you might get a little butt hurt if she doesn’t reply. You make a false assumption. Oh, I guess she’s not into me. I guess she doesn’t like me. No, she’s probably just distracted. If she’s an attractive, stylish woman with a cool life that’s together She has got a crazy amount of online dating options coming in if you’re on the apps. And even if you’re off the apps, if you’re just texting each other, she still has options.

 

Connell Barrett [00:32:16]:

And there’s a lot of stimuli hitting her, and you just want to follow up. So here’s the solution to this. The solution is what I call the 3 times rule. The 3 times rule, which is I would never give up on a woman I’m attracted to, interested in, until 3 good text messages go unanswered. 3 good ones. Not, hey, did you get my last message? Hey, are you blowing me off? Hey, am I going to stay a virgin ginger forever? No. 3 good messages. Humor, heart, jokes.

 

Connell Barrett [00:33:03]:

I can’t tell you how simple this little make-or-break moment is and how it can change everything. So send a second message and a third message and just make sure each one is what I call a value text, meaning you’re bringing value to her. You’re trying to make her smile. You’re doing your best to stay on her mind. There was a woman I was trying to meet up for a date once on Bumble, and she is beautiful. She’s model attractive in my opinion. She’s an artist. She is a dynamite, 9.99999 out of 10.

 

Connell Barrett [00:33:36]:

And she went quiet a couple times. One or two messages didn’t get a response, but I didn’t give up. I said, you know what, send that third message, Connell. Send that third message because she’s an artist. So here’s an example of a value text. She didn’t answer a couple messages, and then I remember thinking, all right, what does, what does Jennifer like, what does she care about? She’s into modern art, art installation stuff. I knew that. So I remember I took a photo of a piece of outdoor art in New York City, like a cow covered in newspaper or something like that, a funky little art installation.

 

Connell Barrett [00:34:16]:

Took a photo of it and I sent it to her and I said, okay, pop quiz, artist. Is this A, a brilliant work of art, or B, just a fucking cow? Inquiring minds want to know. And she wrote back right away, LOL, oh my God, I love that. That is such a cool piece of art. And then she said, sorry, I didn’t get back to you. I’ve been really busy with blah, blah, blah. And the conversation was back on. And that led to us dating.

 

Connell Barrett [00:34:47]:

I would not have had a date with her and dated her. This led to a relationship. And I— that wouldn’t have happened had I not sent the third message. So use the 3 times rule. Do not assume any woman has lost interest just because it’s one unanswered text message. Here’s what women respond to by text. Think of it this way. Here’s your secret formula: persistence plus charm equals dates.

 

Connell Barrett [00:35:15]:

Persistence plus charm. Equals dates. So yeah, 3 times rule. I’ve had multiple women say to me things like— one woman, this is almost a verbatim quote— I sent that third message after the first two, she didn’t answer. I sent her something snarky and funny. I wrote something like, um, dear diary, Megan has gone quiet again. Do you think she found out I still live with my mom and dad? Thinking emoji, something like that. I’m just having fun letting my sense of humor shine, or trying to.

 

Connell Barrett [00:35:52]:

And she wrote back, LOL, or L-O-F, L-O-F-ing L. Oh my God, that was so funny. By the way, I really admire how persistent you are. I like it. Here’s my number. She literally said, I wanted to see how persistent you are. A couple women have said that to me over the years, which means many more are thinking it. So don’t give up after one unanswered text.

 

Connell Barrett [00:36:17]:

Send a second, send a third. Make them fun, funny, authentic, seeking to give value to her. Okay, and this— I rarely say always or never. I don’t make guarantees to a, to a large audience, but I can almost guarantee that if you follow the 3x rule, you will have dates and you will have romantic connections that you will lose out on if you don’t follow the 3x Rule, because persistence plus charm equals dates. All right, thank you so much for listening. Until next time. Oh, by the way, um, if you would like to talk to me or somebody from my team about how my coaching works, because you want to make sure that you meet these make-or-break moments and that you make the approach you flirt on the date, you play to win, not playing to lose. Go to datingtransformation.com.

 

Connell Barrett [00:37:14]:

I do coaching men and women, primarily men, but I’m coaching women now as well. And if you’re interested in learning how my coaching works, you can do a free call, datingtransformation.com, and you and I might just talk soon. All right, till next time.

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Connell Barrett is an NYC dating coach who’s helped thousands of men all over the world find their soulmates while dating with integrity and authenticity. Whether you’re dating in New York or overseas, using dating sites, or wanting to meet gorgeous women in person, Connell can help. Experience your dating transformation with one of the best dating coaches in the U.S.

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I’m dating coach Connell Barrett. I help men build confidence and connect with women by being authentic

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