How to Get a Girlfriend with Connell Barrett - Become a Magnetic Flirt on First Dates in 3 Simple Moves (Live Coaching with Matthew)

Episode Date: September 16, 2025

Awkward silences, small talk that goes nowhere, the dreaded “I’m just not feeling” text. Bad dates suck! In this live-coaching episode, dating coach and bestselling author Connell Barrett helps his client Matthew go from the nice, lonely guy who runs out of things to say to a magnetic flirt who women cannot resist. Discover the 3 flirting moves that Matthew is using to create playful, authentic chemistry on dates. Listen now!FOR A FREE STRATEGY CALL WITH CONNELL TO FIND OUT IF DATING COACHING CAN HELP YOU ATTRACT YOUR DREAM GIRLFRIEND: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:[e-mail]

I didn't just live in the friend's own. I owned real estate there. Welcome back to the How to Get a Girlfriend Podcast. I am your host, dating coach, Connell Barrett. I'm your podcast dating coach. If you struggle with what to say to women, I'm here to help. If you struggle with confidence, I'm here to help. If you struggle to get second dates, get stuck in the dreaded friend zone, I can definitely help

because, brother, I didn't just live in the friend zone. I owned real estate there. And today we're going to do a really cool episode. I love doing coaching call episodes where I record an actual coaching call that I had with my client, Matthew. You're going to hear Matthew. Matthew, he lives in California. He's a business owner. He's about four. I believe. And he's a single dad. And when he first came to me, he was really struggling to get second dates, struggling with the friend zone. He just was having trouble making those sparks happen. He's about midway through my coaching program right now. And this is very typical of a one-hour coaching call that I do with my clients. And you're just going to be able to listen

in and hear me help Matthew with some of the things he's been working on. He's doing so great. I remember there was a moment a couple weeks ago where he said, Connell, I've got three women in my rotation. And tonight I have a date with a Russian-born model. You've created a monster. And Matthew struggled with coming off as a little bit too, what's the right word? Fake nice. He was coming off like a therapist. He was just listening to women and being like a friend. And I said to him at some point, look, it's good to be friends. It's good to be friendly with women, but you can also flirt with her.

You can let her know she's sexy. You can tease her. You can give her a really fun, authentic, true experience of what it's like to be with you. And since he made a couple of flirting and first date shifts, he's really seen some improvement. So anyway, if you struggle with first dates, not sure what to say, not sure what to talk about. women friends own you. Listen to Matthew's coaching call with me, and I'll bet you'll be able to use a lot of the same pieces of advice that I give Matthew on your next first date, so you can start getting second dates, third dates, and soon get a great girlfriend. All right, let's take it away.

Here is me and Matthew. Right, Matthew. Let's get to it, man. What's on your mind today? How can I help you with your dating life? Connell, cool. Thanks. Yeah, no, I got a bunch of questions. the first one I was thinking about is we've talked a little about this, but it's that man-to-woman communication. We kind of touched on this a couple, you know, sessions ago. Really wanted to kind of ask, what does the man-to-woman communication look like on a date? And does that just translate into picking the place or expressing clear opinions? Or can you kind of dive deeper on some of the things you kind of feel are important? A good way to think about man-to-woman communication is have you been on any dates mat where you looked over and saw a couple and

you were just like wow they're hitting it off it's going well they've ever seen that visually and have you ever been and i know you've been on a lot of dates and have you also looked and seen a couple and they're just like he's sitting on his hands figuratively if not literally and they're both being very safe and polite but you can just see there's not sort of a chemical vibe happening? Yes. You notice? So you want to be moving toward that first pair, which is equal parts, physicality, eye contact, the way you look at a woman. There's a way to look at a woman where it's like, yeah, okay, right. And then there's a way that you and I would look at each other if we were getting together as a couple of buddies. Oh, yeah, cool. Right. Yeah, the Dodgers. They're

good this year or whatever we'd be talking about. So a lot of it's vibe. It's eye contact, its voice. It's also clear statements of romantic interest. Probably the easiest way to create, put Amanda Woman card on the table on a date is to say and actually feel, make a statement toward her that lets her know there's something sexy about her. You know what's really sexy about you, Tracy? It's the way you bite your lip when you're thinking you look up and bite your lip. It's super cute. Anyway, I just wanted to say that.

So yeah, tell me more about your college experience. You sort of like throw those little, those verbal and nonverbal cues to sort of crank up the romantic tension on a date. That's essentially how I define man to woman communication. There's really only three ways to communicate with people outside of family. It's friend to friend. It's business slash transactional, which is essentially what you and I are doing right now. Even though we have a friendly coach client relationship, it is a business one. So there's friend to friend, there's business, and then there's man to a woman.

And man to woman is a combination of you just feel it, but it's also how you talk to her. It's what you talk about. Basically, it's turbocharged flirting. And do you think that stays pretty consistent through date, two, three, and four, or does that kind of change you've noticed throughout the dates? I'm several years into dating my girlfriend, Jess, and I still flirt with her and look at her perfect butt. and banter with her and let her know that I think she's hot and sexy and cool. Sometimes I tease her, which is one of the ways I flirt. So, yeah, it never ends.

It'll ebb and flow, and you want to read the room, of course. But, yeah, man-to-woman communication, it's, it never goes away if we do it right. Okay, interesting. Another question, you know, that have come across in my dating world lately, is that of obviously, you know, and I'm sure other guys have, this and they've brought it up to you, but it's those first, you know, five to 15 minutes of like, kind of like, okay, we've met, you know, you don't know me, I don't know you, this like interesting energy slash conversation flow. And I feel like the questions I'm asking my start off sometimes

a little too deep, but like, is there a good kind of cadence or a good flow or good kind of mix of conversations that you're kind of talking about in that first 15 minutes? I think, you know, like there's different stages of the date I like to call it, right? The first 15 minutes are how are you staged in the next 30 day let's talk about us okay then let's dive a little deeper but would love your kind of help and feedback on that because i feel like those first 15 minutes are really for me have been kind of like uh-oh like everybody's nerves are there and i don't kind know what to say and how to drive the conversation well how would you can you give me some examples of what you do say or questions you do ask in those first 15 minutes yeah because you've been

going on a lot of dates as we both know yeah a lot of first dates um and And now second and third date because of you, I appreciate it. So, yeah, so I think things I was asked, you know, like, how is your day? How was, you know, what's been the most exciting that's happened to you this week, other than meeting me? Just trying to kind of keep it general and kind of like open-ended. Again, just trying to like feel where they are and what energy they're bringing to the table on the date. I think those are good options, those first 15 minutes. Really, you're just trying to not.

lose any points in the first 15 minutes by trying too hard or by saying something that's just weird. I don't think that's a Matt problem. That's not a main problem. No. But for the, yeah, for the first 10, 15 minutes, I'm, you know, it's figuratively, if not literally, how about them Dodgers? Or how is the traffic on your way here? Basically, feel, it's, it's okay to to ease into a date with some basic small talk, because you're just letting the two of you get more comfortable in the environment. And it's okay to make a little small talk. It's also okay to be a bit vulnerable.

I remember saying this on many dates early on when I was really nervous, getting comfortable going on dates like 20 years ago when I first started really working on my dating life. I remember, you know that feeling where you're waiting and you keep looking at the door to see if the next woman who walks in might be her? Yes. Because you haven't met her in person yet, you're like, I think that, I don't think that's her, but I'm not sure. Or I hope that's her.

Whoa. She's hot. Or, God, I hope that's not her. Like, different people come in. It's almost like, it's like some kind of roulette thing. Is that my date? And I remember I would be vulnerable and say that to my actual date once she arrived. She would sit down.

And after a couple minutes of maybe chit chat and small talk, hey, how's your day? Where'd you park? That kind of stuff is fine. Then I would say, by the way, I got to be honest, a couple other women came in. I couldn't tell if it was you or not. And I'm just really glad that you are you because you look like your photo or I was so nervous waiting for you to come in. So I might admit to being nervous a little bit if it's genuine, not as a move, but if it's genuine. Because that kind of vulnerability is attractive because, hey, it's a first date.

If you're not a little bit nervous, you know, you're probably not. It probably shouldn't be there for some reason or another. no that's good okay you know it's been interesting i have been saying sometimes oh i was really nervous to meet you and i noticed the energy kind of shifts on the date and uh they they like it like oh really i was too um so that's been interesting so appreciate that no that's that's good advice and then you know kind of even can i throw one more question at you i don't know if we've talked about this on previous coaching calls a really good question to have in your back pocket for the first 15 minutes to sort of move out of small talk to something a bit more real, but also that

totally makes sense. Have you ever asked a woman about the weirdest first date she had? No, I was always trying to shy away, which for sure is a question I had in my head is, you know, on the topic of first dates or dating or boyfriends, girlfriends, girlfriends, you know, on the first dates. It's a follow-up question, but no, I try to stay away from those topics. I get it. In fact, I agree with that. You don't want to go down a rabbit hole of talking about dating or getting each other's exes, probably on a first date. But there is one exception to every rule. And I found it really helpful in the first 10, 15 minutes to say something or to ask or something like, hey, by the way, I'm just curious. What's the weirdest first date guy you ever met

or the weirdest thing that ever happened on a first date. I found that to be a really good question because it's fun, hopefully fun. Hopefully it's not something terrible that happened to her, God forbid. But pretty much every woman has a first date, weirdo story. The guy, some of the answers I've gotten to that question over the years were a woman would say, oh, one guy showed up with plastic vampire fangs in his mouth, and it wasn't Halloween. It was like Easter. another guy showed up, and this was actually in a recent episode, I mentioned this, and he sat down, and within five minutes, he asked this woman I was on a date with, she's retelling the story to me.

This guy asked her what shape and size her are because he's looking to date a woman with silver dollar sized nipples, silver dollar sized aerolas. This is like 10 minutes into her date. And another woman said this guy's Coke dealer showed up in the middle of the first date and gave him. Emma delivery. So I like having that as a good backpocket question for the first 15 minutes because the topic first dates is totally relevant because you're on one with her. And it's a fun way to diffuse some tension. Almost every woman has some weirdo she met. And then somewhat subtly, I like to think that because she is conveying a story about a guy who just kind of creeped her out, you're juxtaposing yourself you're this cool chill well-dressed spoken guy who's so normal and

attractive on some level i feel like that also makes you look extra good because she's almost like comparing the two of you and it's just a fun topic so even though i don't want to talk about dating for that long that's one exception to the don't talk about dating rule and if you have a weird first date story you can certainly share yours as well um i don't have one directly i have a friend we talk about dating. He told me an interesting one. He went out with a girl and he got there and she brought her a six-month-old son. Okay. She didn't know. She didn't know. And he just kind of this child slept through the date. And then he kind of like started a question like, hey, so you have a kid? And she was like, yeah, I probably should have told you that earlier. And they ended up walking.

They're actually now dating full time, but they're dating long term. But yeah, it was an interesting. He's like, hey, interesting way to meet her, meet her child. That's a good one. I know it didn't happen to you. You could share that as an anecdote you heard from a friend. Anyway, feel free to use the, what's the weirdest first date you've met question in your back pocket in those first 15 minutes is a perfectly good way to kind of ease into a date. Yeah. Okay. And then kind of from there, how deep are you going, how deep of questions are you asking, or should I be asking, I guess? The better question is, how deep a question should I be asking on a first date? Like, are you going deep into, topics or is it kind of service level? Depends on the date.

I mean, it's going to change depending on your vibe, her vibe, who the two of you are. But as a general rule, I would say keep it light. Keep it fairly light, fun. Think. Think you can have a deep, you can have an in-depth conversation about stupid shit. That's always been my sweet spot. My first date with my girlfriend now, Jess, we talked for 30 minutes about ketchup and why. she hates ketchup and why I hate mushrooms and why she loves Italian food and roller coasters

and TV shows. We were all over the map in a nice, fun, bantery way. Very light topics. So I'm generally going to keep the first date topics light. And if I'm going to get deep about anything, it's probably going to be more like, I remember on my first date with Jess, I remember thinking we were about 45 minutes and it was very fun and bantery and light. a lot of jokes back and forth because she's very funny.

And then I remember thinking, well, I wanted to be a little bit more deep. So I said to myself, yeah, who are you closest to in your family? And all of a sudden, not all of a sudden, but she opened up a bit and she told me about her brother Aaron, how close they are. And then I talked about my big sister, Kelly, who was the sister I was closest to. And I say was because she passed away last year. but at the time she was still with us, and I talked about that. All of a sudden, we went from banter, fun, light,

talking about why we love dogs and love cats and hate jogging and she hates ketchup to, all right, let's talk about some real stuff. Now, is that a deep topic? I guess it depends on your definition of deep, but I do like to find out who matters to her in her life, who's important to her. I want to know that. I'm curious about who really matters to her,

And I also want to share with her who matters to me in my life. So we start getting to know each other in a slightly different way, if not deep, deep. Did I answer your questions or your question about depth? No, no, no. No, that did. What kind of deep questions or topics have you found yourself talking with women about? I've been trying to keep the first date's light. So kind of was trying to, you know, trying to keep it more on, hey, you know, tell me about travel, tell me about food,

me about, you know, some past experiences you've had as a child trying to keep it kind of light. But some of the deeper topics I've been kind of going into, family has been one. Obviously, even do you like to cook? What do you like to cook? Again, just trying to keep it light. But some of the deeper ones, you know, would love to know about past childhood, family, brother, siblings, things like that. But again, keeping at a certain level, I feel like. It depends on the woman.

It depends on the woman. That's a great roadmap for you. I usually think about a first date more about let's get on the same kind of flirting vibe, right? I love, Jess and I use my girlfriend for obvious reasons, but there have been many other first dates I've had. If you have a nice, light, bantery, jokey vibe with a woman, the topics almost don't matter. You're connecting in terms of how you're talking to each other. other women I've had dates with where it was a lot more more about emotional connection kind of being vulnerable and opening up about fears and hopes and dreams and they are on a more

emotional connection wavelength I've had some women they don't want to talk about their family members they just want to talk about um they just want to laugh and have raunchy on even sexually charged conversations because she's a bit more edgy so I'm looking more to try to match her, her flirting vibe than getting too bogged down in the actual topics. You can talk about almost any topic. It's more about the tone, the tone of how you're talking about that topic. Does that make sense? No, that makes sense.

Okay. No, that makes sense. Yeah. And I know we've talked about this before, this sort of topic, but that helps. Okay. And then kind of in regards to the dates, you know, I know we had talked and was a huge help for me was, hey, you've got to turn the. flirting energy in the, you have to turn up where you're going on the second date.

So kind of want to kind of flow into logistics. I wanted to talk about, so like second, third dates, you know, I can't think you enough. I was having a hard time getting second and third dates. And now I have, you know, women calling me like, hey, when are we going out again? So I wanted to ask. Hold your question. I want to answer it. It's the whole point of me talking to you.

But can you, just for the audience today, can you share any quick stories? from recent successes, moments, moments of connection. As I recall a few weeks ago, you and I were going back and forth, and you started being a bit more direct with women or just literally being more silly, playful. Didn't you grab food off or pretend you were going to take food off of somebody's plate? I don't remember the story, but share any aha moments you've had on dates if you would. And then we'll get back on topic, of course.

Yeah, yeah, no. So, you know, from talking to you, I realize, you know, I really need to be myself. Authenticity is huge. And understanding I am who I am, I have a silly, kind of fun, playful personality, and I wasn't showing that on dates. And went on a date, a first date, with somebody, we met up for drinks, and we were sitting at the bar, and she left to go to the bathroom. I ended up talking to the people next to us for a bit. She came back. back. She's like, oh, that salad looks good. And I was like, oh, actually, I'm going to grab a piece. And I grabbed my fork and went to grab a piece. And she was like, first, she was like kind of mortified, but I also kind of like givly. Right. We had a little bit of banter with the couple next to us for a minute. And I turn my attention back to her. And I'll never forget that she turned to me. And she was like, wow, I really like that you did that. That was really, that was really cool and really authentic. So again, that was the word authentic. She said the word authentic. And I was, she's been reading my marketing. Yeah. You know, Connell. So, but yeah, it's been nice, really to be, to be myself and go out on dates and not trying to be prim and proper. And it changed, you know, working with you again, you know, I can't thank you enough has helped me go from not getting second and third dates to, again, having people like,

hey, I want to go see you. When can I, when can I see you? So it's been a really nice change. And I think it's, it's being authentic. It's been a big, big part of it. Sounds like, well, that story to me says, okay, you're giving her a more impactful. emotional experience. Yes. I think before you were getting stuck in the problem of understandable rut of, oh, let me try to emotionally connect with her. Let me see if we can find the right emotional connection or let me be a good listener.

Let me kind of like just emotionally connect and feel the same way about things. And by the way, I'm not saying not to do that. That can be really successful on lots of dates. But I feel like maybe you were just a little bit buttoned up, so to speak, and holding back. And just, I think women are really drawn to a fully expressive man who's just unfiltered, amplified, putting it out there, doing silly things, like pretending you're stealing food off of somebody's plate. That's, that's hilarious. And that kind of freedom that gives women a more emotionally impactful experience. And women make their dating choices not just on,

does this guy check the boxes I want for a boyfriend? On some level, there's that there. But you probably already check those boxes if she's on a date with really goes on a first and then also a second date is she wants to feel something she wants to feel connection to you yeah she wants to feel like she's with a man who goes through the world and and is on his own path and he's not afraid to speak honestly truthfully let the heavens fall let the chips that's attractive to women because most guys were so guarded and safe. So the reason why I go on and on and on about being authentic and just literally speaking your thoughts up to a point is it's that free expressiveness is very refreshing to women because most men are too focused on what's the right

thing to say to give her to like me. Fuck that. Say that most honest, deepest thing you can think of and as long as it's not vulgar or disrespectful, boom, let it go, let it fly. Yeah, and I agree with you on that. And I think you said this to me, I think in a session we had, you were like, hey, you know, they're prim and proper at work. Like you were like, okay, hey, this is how this sounds and this is, and I'm, as I'm fake air typing here, you know, yes, we will be able. And I realized I was bringing that dating energy to the date and that just doesn't work, right? They get, when you can get that at work, they need something fun and playful to get their mind off of work and off of the normal day to day. You're also being a bit of a rough.

when you do that little pretend. Let me take that food move. You were being a bit of a rebel. You were not caring. You were giving fewer fucks. Yes. And that's attractive. Women want a guy who gives,

not gives no fucks, but gives fewer fucks. That's just more fun and refreshing. So anyway. Okay. Back to the logistics overall question you're asking. Come back to that, please. Yeah.

So you helped me realize that. But I wasn't bringing this date energy to a second date, which for sure I realized I wasn't. Like, hey, like it needs to be a little romantic. It needs to be, you know, just different. Hey, it should be at a restaurant or it should be here. But again, romantic, date, vibe feeling. So the second question now becomes these third and fourth dates. I've kind of mixed it up and done maybe like mini golf or an activity and then like something romantic.

logistics-wise, would love your take. That, obviously, energy from that second date of date-e needs to be there for the third and fourth date. Is that correct? Or is it okay to mix it up and do something like active? Because I'm an active person, right? Like, I like to go to the beach. I like to run, to work out. I'm not going to go work out with her.

I mean, maybe interesting third date. But what sort of activities are you cool with and are you not okay with that drives and continues that energy, but also doesn't feel super datey? I'm thinking through the lens of how can we keep circling the basis, the basis of romance. I don't just mean sexually, but that too, I suppose. If our first date is emotional, romantically, sexually first base, then I'm thinking, all right, I want us to try to at least get to second base. And I work backwards from that, so I'm not thinking one size fits all. for example on you know a first date might be a quick um i don't know a quick drink on a tuesday night

90 minutes two hours you both have work the next day quick and you're just sitting up at the bar having a couple glasses of wine and maybe hopefully it ends with a nice kiss good night but you know you're not all over each other probably hasn't been enough time and if i'm thinking okay date, I want to escalate things. I want to lead that dating dance. And I might choose, yeah, I might choose a place that is a bit more romantic. Nothing wrong with that. But if on the date, if I discover on the first date that she loves karaoke and I love karaoke, well, guess what I'm going to suggest? Date number two, going to a fun dive karaoke bar because that's what both she and I like. And it might be a Friday night. And that'll give us, and maybe we'll go to a second place

after the karaoke place. So the actual thing you do on a date isn't all that important. It's just a vehicle for two people to get closer. And I'm thinking about this through the lens of, oh, well, what's different than what we did on the first date? Because people like variety. You don't want to do the exact same thing on a second date, probably. I'm also thinking, how do we keep moving this romantic dance forward?

And so I'll probably suggest something that's just different, maybe maybe a bit more romantic or more sexy depends or at the very least gives us the opportunity to keep getting closer so any of the things you mentioned are all on the table I think a bit more about oh what would she and both enjoy doing together and also what would be conducive to this further romantic connection slash escalation okay no it's good to know okay so it's not what we do it's that we're together and that the energy is continuing and that we're doing something that is moving this romantic to the next space. Yeah,

I once dated a woman, I'll call her Jennifer. And my first date with Jennifer was a brunch date. I didn't do that often, but it was like a Sunday afternoon brunch date. 90 minutes, we did kiss, but, you know, it was a 92 hour Sunday afternoon brunch date. And then she had to go off and do something with her people.

And then our second date, I'm thinking, okay, how can Jennifer and I get closer? How can I set this up in a way that gives us a chance to just take it one base further and our second date rooftop bar Friday night a more expansive night you know and you know more of a date night than a Sunday brunch and then the second thing I planned was I had a second place in mind to go to so one of my favorite dating first date strategies or in this case a second date strategy is have a second

you can go to if you both want to that's easy to get to so that so i planned out friday night at this cool rooftop bar and i it was a five-block walk from this fun little divey second spot which oh what a nice coincidence was only a few blocks from my apartment yay so i had the second date logistics planned out so that if she and i continue to hit it off as well as I wanted, then it would be really easy for her to then come back to my place and we could do something hanging out at my place, not necessarily have sex, but to just be alone for the first time, which is a further action of things. So that would be an example of how I'm sort of planning out a couple of nights and just making it logistically easy for us to get

closer. Yeah, and I agree with you. It's interesting. I was on a date and we went to like one, we were meeting for drinks at a bar and I knew there's another bird down the street that has like this amazing cocktail. And it was like, hey, we should go here next. And, you know, obviously I drove the date trying to do that, you know, man-to-woman communication. And we got to the second place, had our drink. And at the end of the night, just like, hey, I have to tell you, I really liked that you drove the date and had a second place in mine and just wasn't like, okay, we're just going to sit here

and have drinks. Yeah. Be a man with a plan. You're a man with a plan. Yes. Women love a man with a plan. My girlfriend to this day still says, ooh, I love it when you plan. Yeah.

Boyfriend girlfriend dates. My then different woman, many, many, many years. ago, 20 years ago, actually, one of the first absolute stunning wow women I dated as I started to figure all this out, 20 years ago, her name is Lorraine, she said to me two or three dates in, she said, I love what a good planner you are. You just always have, you have it planned out, you tell me where to go. I mean, I tell, not in a jerk, but like, you know, hey, here's what we're doing. Is this work for you? And women just love that. So, yeah, being a man with the plan, it's such a simple thing to do. Yeah. And I've noticed. And I, and I, and I,

don't know if this is common. You hear this from your other, you know, people you're working with, but I've noticed a lot of women, like I've been lately like, hey, like, it's second date. I'll pick you up and like, oh, you'll pick me up. I really like that. A lot of these women have been asking for like old school, like pick me up, open the door. And look, maybe it's these women I'm going out with, but it's been an interesting thing to hear is like, come pick me up and drive me somewhere for a date. Yeah. You should rent a handsome carriage and a horse and just treat it like it's 1890. If you're lucky, she might show you. you some ankle.

Right. Lucky. And you can finally have sex on your wedding night three years later. Right. No, there's a, look, I'm the most progressive, feminist, men and women are so equal guy in the world. Even me, Mr. Progressive Liberal New Yorker,

I'm still old school in a dating sense. I think it's just sort of the way the masculine and the feminine are wired. Men lead, women like to follow, and they like a man who leads. And I think there's that old school ask. that still is very present in who we are. And so, yeah, be that leader. Yeah, I want to change topics completely here. I'm sure, like, I'm sure you hear this a lot.

Dating apps, dating apps. So one of the things I've been noticing is that I'll have some good banter with somebody on a dating app. We'll have some good conversation, and then they go dark. And I've been kind of, you know, asking some people I'm going out with, hey, you know, I'm interested, you know, to hear about, like, the dating apps, what you think, how they, you know, again, obviously not first date, but second, third date, stuff like that. And they all say the same thing, which I'm hearing, I'm overwhelmed.

There's a lot of choices. There's a lot of people. Like, I get a lot of messages. So I've noticed that some of the people I've been messaging, obviously, go dark and would love some tips or tricks on how to, like, is it, do I need to say something? Should I move those people to the bottom of my list, right? How many messages do you send? Like, what do I say?

I've been trying to, like, add some humor. Like, what's kind of worked for me is like, hey, I haven't heard from you. Should I send a search party? And, like, they'll reply something kind of like funny and keep back. But again, looking for some direction on that. Well, are you sending those really classy dickpicks like I instructed you to? Like the nice ones. Don't just take a selfie.

Have like an illustration penis. That's what works in 2025. Come on. No, I, you know. Kidding. Yeah, it's fine. Some of them, no, I know. I know.

So do me a favor. Can you kind of walk me through the pattern you're seeing of how many messages are you sending? And then when do they go quiet? Can you give me a quick example if there's a, you don't need to use her real name, of course. But kind of walk me through in a minute or so, what the pattern you're seeing. So you match and you swap how many messages? We send two or three messages. and usually that's the point I'm like trying to get it off the app right I'm like okay

two messages and again maybe I should extend that interested to hear but so it's usually two three messages you know banter about something look I'm a big skier so I'll talk about skiing or something within their profile and then usually it's that fourth or fifth message what I notice is there's like a lull right they go kind of dark and then that's when I'll send a follow-up like, hey, like, do I send a search party? But then, like, sometimes I'll get a reply back, like, weeks or, I had one the other day, Connell, that she replied back a month later. And she's like, hey, I'm sorry.

I was on a break from dating, but I got your last message. It was really funny. Yes, let's go out, right? But I just don't know, you know, I'm thinking differently, right? I think that they probably, these women are there, but there's just so many choices that how do I get my message to the top? Well, you live in, you live in L.A., right? So a huge population.

And I've had first dates here in the park where I've said, hey, here, fumble. She's like, sure. She shows me and I look and she's got literally 4,000 likes, 4 or 5,000 likes. I mean, an attractive woman, but not like a male, a female model, like just a regularly attractive woman. So women have an insane number of options. So that's part of the battle we're fighting here as men on the dating apps. I would say my advice here has evolved a bit four or five years ago when I wrote my book and was talking about this a lot. I would say, you know, a dozen or so messages max and then make sure you ask her out, women don't want a pen pal.

I would cut that down to a third of that today. I would say as a general rule, I would say you swap literally one or two messages. And then I would much prefer you say, hey, I got to be honest with you. Big on tons of back and forth messages, but you seem interesting, and I'd like to meet you in real life. Would you be up for it? And B, do that direct vulnerable communication, which is man to woman, clear direct statement of interest, right? That's a clear, that's like the first rule of man to woman communication is clarity. I'm a man, you're a woman, and I'm interested in you. Why would I hide that? And so after one messages, two or three at the most,

you can say, hey, you know what? I'm actually really not a big banterer back and forth, but I want to meet you. If you want to take it to another level, I don't know if you're on Bumble or not, but certain apps allow you to send audio messages. And sending an audio message takes it up to a higher level of directness where you swap one or two quick text,

and then you might say, hey, Tracy, just so you know, I'm not big on tons of messaging back and forth, but you seem interesting, and I want to meet you. Are you up for it? She hears your voice. She hears the confidence you have. That can take it up to an even higher level. So I guess my two-prong, one would be to ask her out sooner or to put that intention out there sooner rather than later, just because that'll save you both time. Women are so tired of pen pal as well. The other thing you can do is read the room a little bit. Don't feel like you have to wait for a certain number of messages.

If your joke or your opener, if she hits you back with like a big LOL, you know, a big hard eye emoji, if you can read that emotional investment in her in that moment, that's when you ask her out because that's when the iron is hottest. So the iron is almost always hottest sooner than later because once you get that brand new match, there's kind of a new excitement. It's like a new match. Where might this go? And then that combined with, she gives you a big LOL or three hard eye emojis, immediately say, hey, let's meet up.

Let's go on a date. Basically, because you want to strike while the emotional iron's hot and not feel like you have to wait for a certain number of messages. Because bottom line, they're going to have so many other options as well. Okay. And then another thing I've been noticing more and more lately is the, again, apps. You know, look, I came from a, you know, on a company, but I have a sales background, right? So I'm like, okay, I'm going to send you a message, you know, and I'm going to, you know, not be crazy persistent, but enough to be like, hey, okay, like I sent a message. You didn't reply.

It's been three or four, unless five days. I'll send a cute another follow-up. I wanted to see your take on, like, how three, four messages, they haven't replied. You're sending them like a week apart and you're like, okay, next. Or are you just like continually, if you think that's a good match for you, you're going to continually. I don't want to come off, again, I'm not trying to be like creepy, but again, we've talked about how there's 4,000 people, you know, this girl had 4,000 likes, which I understand, and I've seen that too, but like, how do you, are you giving it three, four messages and okay, next? Or are you following up six months later? Or you might recall we've talked a little bit about what I call the three times rule, which is I'm going to send three good messages to a woman before I move on and tell myself, okay, she hasn't responded, she's not interested, I'll move on. Three, maybe even. in four, but it's a nice round number or nice round sounding number. The three times rule would be an opener. It's funny. It's good. It's clever. You like it. And no response. And then you wait. I wouldn't

wait a week. I would wait 24 hours, 48 max. Then send the second message. Second message might be a PS to the first in a way. Or it could just take a different sort of angle, almost like you're reopening. Oh, by the way, I noticed that you love skiing, Angela. What's your favorite slope? Or, you know, what's the best place you love to just, you know, crush the powder? Wait, that sounds like cocaine. Never mind. But second message, right?

No answer for that. I would wait. I would send one more. You know, you could do the dear, you know, dear diary, cute girl who skis is missing. Send St. Bernard's search party? question mark. You could do that third little funny one. And then if three messages go unanswered, then I just feel like life's too short. You have options, bro. Like when you and I first met talked, you had like, you know, you were just not getting any second dates and you had a

big scarcity issue. And then I know you're kind of rebooting your dating life right now, but there was a while where you had like three or four different women and a little two or three date rotation, some really good things were happening. So you have an abundant of options if you want them, which is great. And so my feeling is, all right, three, maybe four messages, and then I'll move on. And you never know. Sometimes a massism, she's back on the app and sees that funny final message you sent. Hey, Emily, my mom told me that I should ask you out one more time because she thinks I should kiss a girl before I'm 40. I just wanted to try one more time. And then bottom line is you're not going to lose anything by sending that message.

A month later, she might write you back saying, oh, my God, that laugh. I'm sorry, I was off the apps for a while, but that was so funny. And then all of a sudden, it's back on again. But yeah, three or four, follow the three or at most four times rule. And what makes it not creepy is that you're not asking for anything. You're trying to make her smile. You're trying to make her laugh.

You're expressing Matthew's sense of humor, having fun with it, and going down, swinging. if it ends there. And if it doesn't end, you never know. Some women do come back a few weeks or months later. And then you could still bust on them, tease them if you want. Great. It's so nice you three months later, Kathy. Are you free for our first date in October of 2029? That seems to be the schedule that we're on. You can still have fun with it. But anyway, that's my long winded answer. My shorter answer is follow up, give it. Don't wait a week. 24 to 48 hours, then ping that second or third value text.

And then after three, put the max, then move on because, Matthew, you have options and you don't need to send or 10 messages. Yeah, no, I'm not sending 10 messages, but, you know, the three or four is what I was, okay. And are you deleting the match as a whole? Or are you just like, hey, because I don't know, like, some of the apps I'm on, like, you can delete it. Then it goes, they go back into the queue or like a queue. I don't know how it works.

Are you just unmatched? I don't unmatch anybody or delete them unless there's some reason that I need to free up space to get more matches on a given platform, but I'm not aware of any platforms that work like that. Okay. Okay. Interesting. And then on kind of that topic of adding value, we kind of talked, which I agree with.

And I've had, you know, submissions to that in the past. And it's interesting. I go out on dates and I hear from women like, yeah, I hate the how are you text or where are you or how is your weekend? And I agree. I'm the same way, right? adding value in a text message after a first date

any suggestions on that? Because I notice I'm like, hey, okay, like we've planned a second date. You know, being a single dad, sometimes I can't, you know, meet them for two or three days. So, you know, I want to keep that energy kind of going. But, you know, I don't want to send that, hey, how's your week going?

Or, you know, sometimes I'll try to relate it into like, hey, what do you want to order at this restaurant. I had a date with somebody. And I sent her, hey, kind of embarrassed on this, Connell, I should tell you. I sent her. I'm laughing because I went out with her and before, two days before the date, I didn't know what to send her. So I was like, hey, I'm really looking forward to going to this restaurant. I'm looking forward to getting this dish. And I sent her the menu. And she wrote back, I kid you not, nobody's ever sent me a menu before from a restaurant. but so because of that you get extra brownie points which they also have brownies we will order

but i'm looking forward to ordering this um but you know obviously like is there any way any suggestions or ideas post first date that like i can keep the energy going before the second date because it again might be three four days before that's adding value as a text message that's not just like how's your week going or all right tell me about the last first date you had and you don't user name or real name if you don't want, although it's fine. You can use it if it's not identifiable. Tell me about the last first date you had and tell me two or three, one or two highlight moments of something you laughed and joked about. That's a great question. So the last date I had went out with somebody, sorry, can you ask the question one more time?

because I was thinking about how to answer it. Can you ask one more time? What are some specific things that you and this woman laughed about, joked about topics or in jokes that came up during the date? Or it doesn't have to be a joke. It could just be a topic that were little high points of that date. Moments, jokes, topics. One of them, the last, let's see, I don't want to, I'm not going to give a name.

But I had a date with somebody and we went to a restaurant slash bar and we're there and we had picked a like high top table and she'd come in these like, like, looked like kind of like Cinderella slippers. They were like kind of like these glass, not glass, but you know, like rhinestone slippers. Okay. And this woman walks by, two or three women walked by and said, oh, I love your shoes. I love your shoes. I love your shoes. So I made the joke of, hey, maybe we should switch shoes because nobody can see because my back is towards the wall. I'll wear your shoes.

You can wear my, you know, echo, whatever they were shoes. Okay. And she had a good laugh on like, okay, well, this is a good idea. And we pretended to start to take them off and trade. Great. Great example. Perfect. So she was wearing very, like, Ryan.

Stone sparkly shoes? Yeah, very like heels, very, yeah, like glamorous heels, kind of. So do you know that the stand-up comedy concept of callback humor? No, I don't actually. When a stand-up comedian tells a joke, he gets a big laugh, and then he refers back to that joke punchline 20 minutes later. It creates an even bigger laugh, or at least an additional laugh, because he's referencing.

It's called callback humor. Google callback humor and learn about it on chat or Google or what have you. And not that we need to go down into the comedy right now, but bottom line is if you call back to something that you and she laughed and joked about, that's a really great strategy for finding the thing to text her of the next day. So for example, on that date, you could have the next day Googled, you know, gone on Amazon and Googled a sparkly rhinestone footwear and found something absurd. and over the top or a whole outfit of rhinestones taking a screenshot of that and sent it to her

saying hey w'd be whatever her name was i found what you should wear for our next date totally you and it's just like toe rhinestones sparkles or crazy thigh-high boots maybe that are all sparkly rhinestones it's not doesn't have to be hilariously witty although i think that's pretty funny just the fact that you're calling back to something that you she laughed about you've created a connection, a playful connection, something that you would not send to any woman because it wouldn't make sense, right? But you and she now have a little fun little secret joke. So that's a really, that's one strategy is ask yourself, what did you and she laugh and joke about? I briefly dated a woman named Jen many years ago, different Jen than the Jennifer I mentioned before.

This woman's real name is Jen. And we had a date at a fancy sushi place in New York City called Nobu. And a piece of sushi there was like $20 probably. Yeah. And she dropped two pieces of sushi on the floor. And I, you know, I teased her about, I was just happy to be on a date. She was stunning and cool and awesome. But anyway, the next day I was texting her little jokes like, you know, did you have any trouble eating your cereal today?

Or did you keep dropping the spoon in your bowl, you know, or making jokes about how she's, you know, hey, here's the bill for all the sushi you dropped last night. I take checks or credit cards, you know, something like that. So I'm calling back to things we joked about. That's one thing. Now, if nothing like that arises in your mind with a given woman, you can also just ask yourself, what does she care about? What's relevant to her?

What is to her? And you could ask a question about or discuss a topic that she cares about. whatever that might be. And again, this is also personalized. Personalization is almost always the way to go. What does she care about? What matters to her? I dated a woman who was a painter as a painter, like a professional artistic painter. And I would text her a picture of a painting or a work of art. And I would say, let me ask you this. Is this really a work of art or is just just, you know, a bunch of BS modern stuff? What do you think? I dated a woman who was a sommelier, wine expert. I would ask her wine questions.

because she cared about those topics. They were relevant to her. So I'm always thinking through the lens of, not always, but often thinking, what does she care about, what matters to her? If she has a dog or a cat, I might say, okay, what did boots do today? What dumb thing did boots the cat do today

that just roll your eyes and think, oh, man, I have a cat in the world. It could be as simple as that. So that's how I like to text women the next day. So personalize is what I'm hearing. Yeah. personalized ideally and and or you can also ask questions that might even come across a little bit cliche you just don't want them to sound cliche so yeah I'm not a fan of

how was your day because really do you care how her day was I mean you don't want her to have a bad day but you're just trying to find something right so if you're going to ask how's your day ask it in a slightly more I don't know uh creative way like hey how was your day today on a scale of root canal to won the lottery that's basically the same question but you're using some colorful language to try to make it a little bit more fun for her so you could do things like that okay that's interesting no okay okay yeah those were all the questions i had i mean for for now i'm sure as i continue to go out and dates and reboot this i'll have some more. Okay. Awesome. Great stuff. Well, you got me by text, obviously, as you know,

available by text six days a week for you and all my clients. And we'll talk again next week and not recorded for the pod. But we'll talk next week and keep me posted on how things are going. But no, I just want to say how proud I am of you because you've gone from not getting second dates having women give you the whole hey i'm just not feeling it to um really seeing some nice wins and and having two three different women on your dance card at any given time and uh yeah it's just a matter of who ends up being um matthew's amazing girlfriend not a matter of if or when it's matter of who she is and uh yeah i'm so glad that the way i coach has helped you so thank you and i can't thank you enough connell you have you have no idea again i was the had a date

last week or maybe it was a week before and I'm out with somebody and they're like I want to see you again. It was the first time I was like, I'm not really interested in them. Usually I'm the one again. So it's been, you know, the advice you've given me authenticity and all the other stuff has really helped. I like that. I'm sorry that you weren't more into her. But yeah, that's a great feeling. Once women start saying, hey, when are you asking me out again? When are we going out again? That feels so good to be wanted and desired. I know you're starting to feel that in some real ways. All right, Matthew, until we speak again.