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You Like Her, But You’re Trapped in the Friend Zone. Flirt Like This to Escape (Live Coaching with Matt)

41m 51s

You Like Her, But You’re Trapped in the Friend Zone. Flirt Like This to Escape (Live Coaching with Matt)

In this episode of the How to Get a Girlfriend podcast, dating coach Connell Barrett and his client Matthew discuss improving dating app interactions and first dates. Matthew, a 40-year-old California business owner, reports that conversations on Hinge and Raya often go quiet after 3-4 messages from each side, just before he would ask for a date. Connell advises a preventive approach: ask for a date after 8 total messages or one topic, showing intentionality and reducing chances of silence. For re-engaging women who have gone quiet, he recommends sending personalized, value-driven messages about her interests (e.g., her dog or a shared hobby) rather than direct date requests, using a "give, give, give, ask" strategy. He emphasizes persistence plus charm, noting that waiting more than 48 hours risks being forgotten among her many matches. He also suggests messaging in the afternoon or evening for better response rates. Matthew then shares that he often gets friend-zoned on first dates, feeling too friendly and not flirty enough. Connell begins to address this by defining flirting as "play," but the response is cut off, ending with the host acknowledging the challenge and offering to continue the advice. The episode focuses on converting app matches into dates and adding romantic tension to in-person interactions.

Transcription

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English
Stop thinking so much about what's the right thing to say? Instead ask yourself, what is the deepest, truest thing I'm thinking about this woman and just say it? Welcome back to the How to Get a Girlfriend podcast. I'm your host, dating coach, Connell Barrett. I am here to help you know what to say and to flirt like you mean it. That's my new tagline, by the way. Hope you like it. Anyway, speaking of flirting like you mean it and a guy who has really achieved some incredible dating successes, I'm joined today by my client, Matthew. Matthew is making a return appearance to the show. He and I have been working together for a little while and he came to me long ago, struggling with flirting, struggling with first dates, just having some tough issues, getting first dates to convert. And he's back to ask me a few more flirting and dating questions. Welcome back, Matthew. Connell, thanks for having me again. Yeah, I kind of I just want to start off by saying I can't thank you enough to success. You've. Yes. Thank you. Thank you. Thank you as much as you want. Go. I can keep on going, but no, I can't thank you enough. You really help me open up a new flirting channel and a new way to engage women that I never thought was possible. So I can't thank you. Well, you and I are both businessmen and we talk about things like funnels and bringing in business success. And I kind of like to. I like a guy to look at his dating life, almost like we're launching a, a new business funnel, but for his love life. And we need to get that funnel filled with quote unquote leads, right? The Glen Gary leads the dates. And you're main funnel of Glen Gary leads of really cute quality women. And by the way, just for those of you who never met Matthew, he's 40, California, business owner and single man who is just trying to find the one. And you're on the dating apps, right? That's how you're getting most of your dates. Yeah. I'm on hinge and rya currently. And which kind of leads me to an interesting question I wanted to ask you. I seem to be getting some good kind of banter conversations going and some even good conversations going, but then they seem to drop off after three, four days. And I'm wondering if you had some ideas on kind of how to reengage in like a flirty kind of fun way. That's not, hey, you know, cheesy and one liney, but something that I'll kind of draw them back in and reengage in the conversation. So obviously we can take this conversation off the app and hopefully meet in person. So you're saying before you've met her, you mean, right? Before, yes, this is before. So we might have been chatting for a couple days on the apps, you know, kind of some messages here there. Hey, tell me maybe like what's your favorite restaurant, you know, something engaging. And then there might be two or three, maybe four days max of silence. And I'm always kind of wondering, okay, should I should I reengage them? How should I reengage them? What's a good message or do I just say move on to the next one? I'm trying to kind of figure out thinking more of the messaging though more of sure. I'm more back back. Ballpark number, how many messages have you sent back and forth with the typical woman you've matched with when they go quiet? That's a good question. I was like, should I go look at my phone right now? Probably usually three or four messages. I think it's like right at the cross, like asking for the number of trying to get off the app. Okay. So like three or four from you, three or four from her and then silence. Yeah, yes, three or four from me, three or four from her and then like right, it's literally the next message would normally be like, Hey, do you want to connect off this app and meet up? I want to take you out on a date. And again, so like one or two topics, would you say you've reached or maybe one topic? Ballpark number. I'm asking for agnostic reasons. Yeah, no, it's usually about three, I'd say topics three topics. Yeah. Okay. All right. I'm a kind of banter guy, like to kind of throw different topics in there, kind of, you know, nothing like changing from. Let's talk about the weather, but something maybe like, you know, like restaurants, and then maybe we're talking about vacations or trips. Okay. I would say all things equal and every woman's different. But if you want a general thought here, once you get to 10 total messages, ask her out. Even eight total. So you might already think of it as eight messages total, maximum, ask her out. And or you could also think of it as once you, once you're done with a first and are in a second topic, that's enough to get her off the app. So I think my best advice for you here would be preventative measures. Now, I'll tell you what to say when they go quiet, but they're actually not going, they're going quiet because they're probably waiting for you to ask them out or to move this off of the app. I'd rather you hear from them, Hey, why don't we text, I'd rather you ask her out and send like two or three messages and then say, Here's a really good. Here's, here's talk about what to say. Here's a really good thing to say. I'm just looking at dating profile. Let's see here. So here's a woman I matched with on Bumble. And by the way, this is for coaching purposes. I have a girlfriend with whom I madly in love. We have two beautiful little orange tabbies. So for what it's worth, dear listener, this is just for coaching. I'm not meeting her. But I am on the app. I have a really weird job. Anyway, so I matched with a woman. I'll call her Brooke, okay? Brooke and I matched beautiful, attractive, stylish, just fantastic. Hey, Brooke, she just wrote, Hi, I'm Bumble. I wrote Hey Brooke TGI Monday. If there is such a thing, my second message, I'm curious. Are you as charming in real life as you see him on your Bumble? Thinking emoji, happy face emoji. She writes back, Ha, ha, while you have to find out in person. So we are now three messages in. She's only sent one. And now she is basically saying, ask me out. So something you don't have to act this quickly if you don't want to, Matthew, but something you could do is one because you like to banter. So do I. But the goal of messaging a woman on the app isn't to banter, although I love banter. It's to get her on a date. So I would say try to find a nice middle ground banter for three or four messages. Total about one topic and one topic only. And then transition to asking her out or getting her off the app. So that makes sense so far. That makes sense. So we're saying four messages. Sorry, 68 messages total, total, not per person. Right. And that's a guideline. You want to read the room, read what she's giving you, not say, connoisseur eight messages. So eight messages. How long I wait? Don't do that. I would rather you ask her out sooner rather than later, because that shows intentionality. It shows your guy goes for what he wants. Okay. And I think some of these women are going quiet because there may be they're not banterers like you are or maybe they, and there's other reasons why women go quiet. But if you want one of my, it's the simplest line in the world. I've sent, I've had many dozens of clients send this. And here's a, you, this is so copy and paste. It's not even funny. I'll say it again. I'm curious. Are you as charming in real life as you seem here on insert app? It's a leading question. I should have been an attorney. It's a leading question, right? Because most women say, well, of course I'm, of course I'm as charming in person. What is she going to say? And then what would you say, Matthew? I'd probably say something lines of, well, I need to see this in person to verify this. There you go. Perfect. Yeah. Okay. Or some women are a little snarky like you and I are. And someone, some women have said to me, oh, I am absolutely boring as hell in person. I'm a total drab. I'm, I'm, I'm like a zombie. I mean, what would you say to that? No, no wrong answer. I'm just curious. I usually like to come from a playful kind of challenge place. So I'll say something maybe long lines of, well, I'm always up for a challenge. Let me see if I can change this. I love it. I was about to say the same thing. I'm, I'm deputizing you as my assistant coach. Yeah. I wish. Like I love, I love a challenge or the idea of an improv, they say an improv. There's this concept called yes and you say yes to the premise. And then you add to it. So oh, yes, I love boring women, boring women are my favorite. Let's meet up. You don't even have to talk. I'll do all the talking. How about Friday night? So you basically, you just agree and add to it. Bottom line is I think preventative measures are going to be a bigger help for you than what to say next. But let's say she goes quiet for whatever reason, three, four, five messages in. She just goes quiet. What is your current strategy if any? They're using. I try to keep it. Usually after two to four days of being quiet, like if we, okay, we've had some good banter or some good conversation and messages are flowing pretty frequently. I'll try to obviously take it to the next level meet or. I'm connecting off the app, but if it goes quiet after that, I'm usually just sending a follow-up like, "Hey, would love to take you out on a date." I'm wondering if you're free, obviously, next week, next week. Something very kind of basic, but I think it needs more of an umpt, but I can't figure out what it would be. You're a business guy, right? I am, yeah. Let's say you're sending a marketing message to somebody on your mailing list. You're interested in your product, possibly, and they, you want them to buy. But first, you have to get their attention. What do you think would work better? You ask them to buy when they've gone quiet, or you try to engage them with something that maybe a tip or an insight or something emotionally stimulating to get them responding to your quote unquote, "reach out." What do you think would work better? I think the tips are going to get more engagement. Yeah. That's a good way to think about the next message to send when a woman goes quiet. When a woman goes quiet, it's usually, there's multiple reasons. Beautiful attractive women, especially, have hundreds and hundreds of options coming in. Sometimes thousands, but hundreds of people are matching with her. The way we stand out is persistence plus charm equals dates. I would say by charm, I just mean you're giving value, right? You're seeking to make her smile. When a woman goes quiet, I wouldn't message her and say, "Hey, do you want to go on a date?" Because she wants some kind of emotional engagement, most likely. Better to make her smile, make her giggle, make her laugh, or just make her intrigued by something she finds interesting. Without naming names or identifying anybody, can you give an example of a woman you match with recently on an app and you're like, "Oh, man. What can I have said to her? We can use a quick little case study if you want." Yeah, I was going to look through my phone. I know I was mentioning this girl named Jessica. Okay. Yes, and we had some nice banter, some conversation today, obviously earlier in the week, and then it just went quiet the last three days. I sent her the last message. I can read it to you if you want me to. What was your last message? Jessica, sure. Let me pull it up. We were talking. My last message to her was, "Hey, explain yourself in five emojis." I like that. I like that. That's not bad. I've heard of her doing a little work, but it's not hard work. It's fun. That's a great example of trying to talk to a woman on that emotional wavelength. I like that. It didn't work, though, for whatever reason. It might not have been anything wrong with the technique. For whatever reason that didn't engage her, or maybe she read it in the middle of doing 17 things at work. Then 12 other guys went to the top of her queue. Based on what you know about Jessica, what are a couple of things about her that you know she cares about or that are relevant to her? I know she's a dog. We've talked about that. Our favorite things is we live close to each other in Los Angeles. We talked about that and we talked about both loving the beach. I love it. If a woman like that goes quiet, rather than asking her out, I would say ask yourself, what does she care about? What would she like to message about? What might engage her? In her case, she likes the beach. She likes her dog. I love her dog. You might say, "Hey, pop quiz, Jessica. What is the cutest thing that your dog does that just makes you melt?" It's like, what dog mom would not want to answer that? I see. I'm looking at my phone from many, many years ago, but I was trying to get a really attractive and frankly, just cool, dynamite smart. What I call a wow girl from Bumble to respond to me after a few messages. She went quiet after a few messages. She is an artist, an actual literal painter. I thought, "How do I get Jennifer to write me back?" I'm looking at the message right on my phone right here. I was out and about in the city and I saw this art installation, like an outside art installation that showed a cow covered in, I'm not a very articulate at describing art, but with paisley, multi-colored, imagine a paisley cow. I took a photo of it and at this point we were texting, but same difference. I took a photo of it and I said, "Okay, Pop Quiz." One of my little pet phrases, "Okay, Pop Quiz. Since you're an artist and therefore an expert, is this a) legit art or b) just a damn cow? She immediately wrote back and I can't even read her response. I mean, I can. It's just, it could go on forever. She wrote back saying, "Oh my God, I love that. I love what that artist did with the colors. I've been where you took that." Back, back engaged and we ended up meeting up, having a date. So bottom line, I didn't think, "What's in it for me?" When I messaged her, I thought, "What would make Jennifer respond?" "Oh, she loves art. She's an artist." That's probably a good way to get her engaged. So I prefer a personalized message that engages her on something she cares about, her dog, her favorite hobby, or whatever has already worked with her in the past as a good place to start. Makes sense? Now that makes sense. And kind of an interesting sub-kind of question from this. Is there a better time to message? I mean, obviously, is it during the day, is it at night? Have you noticed any sort of. 6.37 pm on a Tuesday is the perfect time. Only message women on that day and time. Otherwise, you need to make pants. No, I was interested. I was like, "6.30. I'm like, "Oh, okay, I can make that work." I only got Tuesdays. I like this. But no, I was. I love the. I'm trying to figure out, is it before work, after work, obviously, I feel like it's a very interesting. I mean, look, some people are on their phones all day. Some people aren't. So I didn't know if you had any suggestions on that as well. I wouldn't overthink it. If I'm going to give you a guideline, I would say, "I'm going to give you a guideline. I would say, maybe don't ask her out at 7.15 in the morning when she's commuting to work and I'll stress out and be worried about what her boss is going to say." But that might be a great time to send her coffee porn. Take a picture of the cappuccino you just ordered. Send her a picture of the cappuccino. My coffee can kick your coffee's butt. Or something like that. And then you have flirting and engaging, I get it. It's like giving value. I used to say, "Give, give, give, ask." Put another way. Play, play, play, pull the trigger. What is flirting? Flirting in a word is play. It's literally described to define in the Oxford dictionary as playing at love. That's what flirting is. It's play. So think, play, play, play, and then pull the trigger. Pull the trigger, of course, means ask her out. But if she's not playing with you, pulling a trigger, you're going to get blanks probably. If you get her playing with you again, "Oh, ha ha ha, oh my God, here's my coffee today." And then all of a sudden, you're messaging about coffee, which is a perfectly light topic to be messaging about. And then you can ask her out at that point. But the guideline is, I would say, "Yeah, you do want to be cognizant of what time of day it is. Monday morning, I wouldn't ask her out." But maybe in the afternoon or evening, maybe it's happy hour. That's not a bad time to send another message. People are in a typically a better mood at the end of a work day than they are on their way to work. So you want to don't over think it that much. But I would say asking a woman out would make sense to do in the afternoon or evening, generally speaking. That said, doesn't matter what time of day. Somebody like you can get a woman to be like, "Hell yeah, I want to go on a date with this amazing guy, no matter what time it is." I see what you're saying. Okay. Okay. One more thing. You would not wait more than 48 hours, maybe even 24 hours, but 24 to 48 hours is the most you should wait before you message a woman again. Do you know why? Pop quiz. No. No, I don't. I wish I did. You've been on many dates, right? Have you ever, by any chance, asked one of your dates to let you see her inbound messages from men on Hind and Raya? No. I'm going to-- Have you ever-- The next date, ask-- and your next first date, ask her how many matches she has or how many likes she has. It'll blow your mind how many men are trying to match with her and date her. I'm sure. I'm going to make it. I can't imagine. Yeah. Yeah. So, like Sidney Swini wouldn't have as many matches as some women I've seen. I was on a first date, many, many moons ago. [BLANK_AUDIO] actually right before I met my girlfriend, 'cause I remember in the lead up to meeting Jess, but I was on a first date with a woman from Bumble, a very attractive single mom, 40 plus, very pretty, very successful, but not like cover model, just like an attractive, dateable single mom. And I looked at her Bumble, she had 4,000 likes. 4,000. 4,000. So my point is simply that, you gotta stay on her mind. If you wait three or four days, you're just going way down the queue. Okay, go persistence plus charm, give, give, ask, "Panger once a day." Or at the most, don't wait more than 48 hours. Otherwise, you'll just be out of sight and out of mind. And as long as you're giving value, you're not gonna come off as a needy. You're not gonna bother her, because you're that guy who is asking the charming question about her dog, or sending her the funny coffee photo, or the picture of your cat doing backflips or whatever. No, that's interesting. Yeah, and that kind of, it's interesting, it kind of leads me to kind of my next kind of question I have, obviously it's like, you know, I'm going out in these dates, which is great, you know, but I think sometimes I come off kind of too friendly and not flirty enough, but I don't want it to sound like forceful or awkward or kind of weird. So I'm trying to, I don't want to be awkwardly flirting. So I was wondering if you could meet some kind of advice on that. Like I think I'm coming off to our cross too friendly on these dates, but not flirty enough. Can you elaborate what you mean by that? Yeah, like I'm going out in dates and I've had a couple dates where girls are like, oh, you know, the end of the day, they're like, oh, you seem really nice, but just not my type. So I think I'm maybe getting put in the friend zone or maybe I'm coming off, like I'm not flirting or maybe I don't want to sound awkward, so I don't want to like flirt with them, but I don't know how, it's like a, I don't know how to put it. It's an interesting question, but I guess more of it's like, I'm getting on first dates, I'm going and then I'm there, but I don't know how to flirt. And I don't know if it's flirting or if it's I'm coming off too friendly to them, like, or what it is, right? Okay. I know that feeling and I remember feeling that myself because I'm the nicest guy, kind of guy in the world that I'd like to think on in my better days. So it was really frustrating for me when I was struggling with that. The insight I want to offer you is there's nothing wrong with friendly, friendly kind. That's exactly what women want. We just want to make sure that there is an edge, there's a flirtatious risk taking side to you as well. And then you're giving women what they want, which is, oh, a kind, nice guy who also is not afraid to look me in the eye and make a clear statement of romantic intent, which is what you always want to do on every first date with a woman you find attractive. You want to give her a clear statement of interest, romantic interest. It could be as simple as saying, you know what's really sexy about you? It's blank. My first date with my girlfriend, my now girlfriend, I was just so blown away by how funny and witty she is that I looked at her at one point and said, you know what's really sexy about you? You're so quick-witted and funny. I'm usually the funny one on a date. Now, I'm just trying to keep up with you. And she later told me how that really resonated with her because she's used to guys saying, oh, you're so pretty, you're so cute, but I was the guy saying, okay, yeah, you're cute, but wow, what's really blowing me away is how witty and smart and intelligent you are. So, fastest way to make an impact with flirting is tell a woman, let her know with clear simple language what you like about her and why you like it. And ideally make it a trait, not just a physical thing. Do you do that on most first dates? I don't, but now I'm going to. Okay. And the thing about clear statements of romantic intent is that this is, it shows your interest, it shows you have the confidence to say it. It's also flirting. It's basically, hey, I like you. Do you wanna go on another date with me? It's vulnerable, but it's all, because it's vulnerable, it's also, it shows confidence in yourself and a willingness to lead that dating dance. And if anybody out there listening is struggling with what to say, stop thinking so much about what's the right thing to say? Instead ask yourself, what is the deepest, truest thing I'm thinking about this woman? And just say it, as long as it's not vulgar. (laughs) And as long as it's not crazy needy. Okay, you don't wanna be super needy. What I mean is you don't wanna say, oh my God, I haven't had a date in four years. I'm so glad you're here. Don't be that honest. (laughs) Okay. But also don't say, I wanna take you back to my apartment and do XYZ to you, your hot naked body. Don't say that first. Say that later in the night when things are going amazing. There's that sweet spot in the middle. So simple, I don't want anybody to just script out what they say. But if I had to give somebody the what to say, I would say use the word sexy on a first date. You know what sexy about you, Amanda? You're so bold and courageous and you backpacked through Europe all by yourself. Oh my God, that's so cool and sexy. I'm not used to meeting women like that. You have to believe it, you have to feel it. But yeah, women like a guy just tells it like it is. That's what the bad boys have going for them. Quote on quote. I would love to say that and I will. I just, you know, I don't want it to sound awkward or forced. But I mean, I think it's a it's a great idea. I'm gonna implement it. Awkward is most of what makes something awkward is you not committing to whatever the move is in this case, clear statement of romantic interest. So if you say, you know what, can I just tell you something? I hope this isn't weird. Oh my God, Amanda, you're just really sexy. I'm sorry, is that creepy? Am I being creepy? Like that's fucking awkward. What I just did there. What if you say, you know what, Amanda, you know what's really sexy about you? You just say exactly what you think. Your brain, it's like you're all over the place in a beautiful way. It's like bumper cars up there. I love it. I love the ride I'm on. It's really sexy and cool. Just owning it, there's nothing creepy about that. So so much of it is commitment, commitment to what you're saying. It's hard to be, it's hard to make that creepy or awkward. It's not, there's nothing creepy about being honest as long as you're speaking from a true authentic place. I appreciate that. No, that's good advice. And then, you know, I mean, even on these dates, you know, you kind of, we talked about it a little bit and you like a couple minutes ago, but like, I feel like I'm running out of things to say. Like, and I don't want it to get awkward and you know, those have those moments you like, oh, like, is she going to talk to me? I don't know what's going to happen next. Who's going to speak? And he's suggestions on how to keep the conversation going. Yeah, running out of things to say, I feel you. I remember, I remember I used to bring a 8 1/8 by 11 sheet with like 14 cool things to say. And I put it in my back pocket, back when paper was a thing in the world. And I would go into the men's room in the middle of the date and like, OK, say the cool, tell the cool, tell the cool story about my trip to Italy and say this or that. So I remember that feeling. Here's the-- let me hopefully shine a light on this for you. By the way, my cat is sitting on my lap as I talk. I know. But this happens not because you're not good at saying things, but because the bar is too high for how good what you think the conversation needs to be. So we want to lower the bar for how good the conversation is. And if you believe in whatever you're talking about, that's going to resonate with a lot more women. So don't think what's the right thing to talk about or what's how to talk about it in an amazing way that's like good content. Just think about, OK, let me share about my life. Let me share a travel story. I have a back pocket topic so that when you do get in your head, you can say, OK, I'm going to-- I'll tell her about my trip to South America. And if I really get in my head, I'll also ask her about the fact that she loves the beach and ask her what her favorite beach is. So give yourself one or two back pocket topics so that if you do run out of things to say or start to, you can just kind of break glass for topic. And the nice thing about this is having that emergency back up topic usually means you won't even need it because you're not worried about running out of things to say because you have something to lean on. OK, that makes sense. So I like that. I actually have been going to the bathroom. I'm like, oh, yeah, what was I going to talk about? So I'm glad I'm at the only one in Connell who's scrolled through notes on their phone or piece of paper. If you don't do this already, you could look at her hand or her raya literally on the way to the date and say, OK. Emily, she loves musical theater. And she's into science. Oh, and she, her family just did a trip to Ireland. OK. And you can just have one or two of those topics ready to talk about. And you probably won't run out of things to say in part because you're not worried about it because you have your backup plan. OK. OK. And then I had a great first date. last week, Monday. Good conversation, everything flew and you know we really enjoy each other and then I kind of I don't know what to do. Like I'm like I want a text, do I text right after the day, do I text the next day? I don't even know what to say. I don't want to sound needy and vague. Hey, I had a great time but like I don't heard a thing I'm not interested so I was wondering if you could be some advice on that. Yeah, you want to show interest but you don't want to come off as needy but you don't want to go quiet so you probably feel like you're stuck between a rock and a hard place with what to text. Is that what I'm hearing? Yeah, yeah. More of more of the rock than the hard place. Okay. Are you worried about double and triple texting or just not coming off as needy in your texting? Oh, I already double and triple text so that's not. That is like the least I like him but it's more of like the needy. Like you know I don't want to sound like oh I'm desperate but like hey like I had a lot of fun but I want to see you again so I don't know how to draw the line between needy and desperate and maybe cool. I guess it's a good way to put it. Okay. Well one of the core ways of flirting is letting a woman know what you want. Two of the sexiest words in English language to a woman is when a man who she had a date with says I want. It's not needy to say I want to see you again or I want to take you out for a second date or I want you to know how incredible tonight was. That's what I'm talking about by clear statements of intent leaning into that authentic self and letting her know that you're into her. There's nothing needy about that. What's needy would be sending her nine messages. Did you get my last message? Do you like me? How do you think the date went? Oh I'm so sorry I shouldn't have said that thing and apologizing for yourself. That would be needy but you letting a woman know you want to see her. You're actually giving her what she wants. You're giving her certainty and you're being the man of certainty which every woman wants in her life. Okay. And then how soon after the date do you suggest texting? Is it one hour, 37 minutes and 12 minutes? You know I'm very little. A little mountain time and then that's totally different set of rules. Okay. Let me ask you this. Who is your dream woman? What famous woman would you just be like oh my god Connell? If that was my girlfriend I would be over the moon. Connell when I was like 16 17 was cured nightly. I'm so embarrassed to say this. Okay. Definitely change since then. Probably right now I'm going to go Sydney, Swini. I'm going to say. All right. Let me ask you a question. Here's a thought experiment Matthew. You have a first date with Sydney Swini and it goes pretty darn good. She's wearing her jeans you know because she's always marketing. It goes really well. And Sydney Swini before she gets back home in her Uber she sends you a text and says hey I really had fun meeting you Matthew. I can't wait to see you again. Would you A goes to her because what a needy bitch sad or would you say yes Sydney Swini's into me and take out a billboard telling everybody you know. I'm going to go with B but can we include C as probably text on my buddies and be like hey no he's going to believe this but okay so why is it not needy when she messages you that. That's a great question. I guess it's because there's the feelings are mutual I guess or like because I feel that I don't actually even know how to answer that. Yeah I don't know how to answer that one I hate to say this but yeah I feel like it's maybe it's because there's a true connection and I'm truly interested in her and I guess right when you're very good. Because you see value in her romantically what she can bring to your life right. You want her to like you right yes yeah because you see oh my god I would love to date this woman she has so much to bring to my romantic table something like that fair to say correct yeah fair to say right she's a 10 right you want to look at yourself and project that version of yourself when you're on a date with a woman which I know you are you're telling because you're telling me how many how loose and fun and in the zone you are in first dates you want to remind yourself that you're a well I guess what I'm saying to you Matthew is you're as beautiful and sexy as Sydney Swini. Maybe not me you don't look quite as good as she does but it comes down to the perception of value that that person hasn't you and that's really what dating comes down to is we look at the other person and say is this person the kind of person I want in my life and if that person is that kind of person if they have a lot of they have a lot to bring to your table then you don't have to worry about you letting them know you're interested a core tenet of flirting is just clear language letting a person know you like them and what we don't want to do is get to go too far down the rabbit hole of all the bullshit on TikTok and YouTube where it's like don't you know play it cool don't let her think she's into you make her make her wonder if she likes you maybe maybe 25 years ago that might have worked a little bit but in the dating app world whenever you attract a woman has hundreds of options that shit doesn't work plus it never even if it worked it just feels bad and rather you get in touch with your core worth you know you offer as a man that you're a regular guy 10 Sydney Swini is a society 10 you're a regular guy 10 I'm a regular guy 10 I like to think when I was single and you want to communicate with women from that place of of oh I'm a 10 I'm a regular guy 10 Sydney Swini has countless dating options if she wants them right I'm sure yeah so do you though how many matches and dates are you getting on the match on on the apps tons and tons right correct yeah you have an abundance of options so I want you to project a side of you on dates that is hey I have an abundance of options I'm an amazing guy but tonight I'm with you I hope we hit it off and if you like her there is nothing needy about a high value authentically awesome man letting a woman know that you're into her and want to see her again nothing needy about that if you came off as super needy and insecure and didn't have a good date then that would be bad but it's not about what you text us about what you're giving around the date I see okay it makes sense and then you know some some other things that have also come up is you know picking up women not from the apps right it's a farmers market super market restaurant bar I don't want to use cheesy pick up lines but I don't want to be boring and I don't know how to flirt naturally in those situations any suggestions like about how to break the ice out in the real world break the ice and then how to even break the ice with some flirting right so it's not like hey here's my pickup line oh you're picking up the soup oh let's wait I don't know you know right yeah it's so scary to know you want to meet a woman out in the real world but then not know what to say and my clients and I deal with this I used to deal with it all the time you don't need to say something amazing you don't need to use some canned cheesy pickup line if you use a scripted planned pickup line you're just going to sound like a robot that's not what women want so what you want to do is give yourself one of three simple options I call it the what to say framework here's how you know what to say so you see a woman at the farmers market and you choose either you want to ask her a question that makes sense you want to give her a compliment that's g-rated or you want to make an observation about something that you notice and then you use one of those three options as the way to break the ice so question compliment or observation so for example my client Robbie was at Starbucks not long ago and he saw this woman next to him and she put five sugars in a small or a tall coffee at Starbucks five sugars so he observed that instead of some planned pickup line he said hey I see you take a little bit of a little bit of coffee with your sugar just a dad joke and she giggle and said yeah you caught me I have kind of a weakness for sugar and then they chatted for a couple minutes next thing you knew he was getting your number and they went on a date the very next night so he didn't need to use a planned pickup line just look at the situation and go okay compliment question observation and whichever one you choose it's 90% rejection proof because there's nothing sexual there's nothing creepy it's just simple basic friendly social conversation and that's how you start a conversation that can lead to a date okay no I'm going to try that appreciate that one that's a good one okay I think those are all the questions I had okay for this week great next question for you is when is your next first date any plan um I think I have won this week friday and then oh Maybe another one Sunday as well. I'm trying to close the deal on that one. Okay, fantastic. So on your next first date, I would say, assuming you are genuinely liking her, look for a moment midway through the date when you just give her that clear statement of interest. You say, "Hey, you know what I like about you or what's charming about you?" Or if you're really feeling it, you know what's sexy about you? Putting that what I call man-to-woman communication out there. That's what keeps guys like you, me back in the day. That's what gets you out of the friend zone and getting a lot more second and third dates. And even if she's not the one for you long term, women just love a guy who just is not afraid to lead that dating dance and to flirt like you mean it. So yeah, flirt like you mean it. - I'll give it a try, I appreciate it, Connor. - Cool, man. Hey, thanks very much for listening, by the way. By the way, if you, like Matthew, would like to talk with me about your dating result and taking them to a new level. And if you struggle with flirting, if you struggle with what to say, then go to my website, go to datingtransformation.com. You can book a free consultation call with me. And we can get on the phone and talk about how we can get you flirting like you mean it and getting you really good at what to say and flirting and getting you out of the friend zone and into a really good romantic chemistry with women on dates and in real life and on the app too. So go to datingtransformation.com until next time. Thank you so much. - Thanks, Connor. (upbeat music)

Podcast Summary

Key Points:

  1. Matthew struggles with conversations dropping off on dating apps after 3-4 messages; the host recommends asking for a date within 8 total messages to prevent silence.
  2. To re-engage women who go quiet, use personalized, value-giving messages about their interests (e.g., dog, beach) instead of direct date requests; persistence plus charm works.
  3. Avoid waiting more than 24-48 hours to message again, as women often have many matches; time messages for afternoon/evening for better engagement.
  4. Matthew feels he comes off too friendly on dates and gets friend-zoned; the host suggests flirting as "play" to avoid awkwardness, but the advice is cut off.

Summary:

In this episode of the How to Get a Girlfriend podcast, dating coach Connell Barrett and his client Matthew discuss improving dating app interactions and first dates. Matthew, a 40-year-old California business owner, reports that conversations on Hinge and Raya often go quiet after 3-4 messages from each side, just before he would ask for a date. Connell advises a preventive approach: ask for a date after 8 total messages or one topic, showing intentionality and reducing chances of silence.

, her dog or a shared hobby) rather than direct date requests, using a "give, give, give, ask" strategy. He emphasizes persistence plus charm, noting that waiting more than 48 hours risks being forgotten among her many matches. He also suggests messaging in the afternoon or evening for better response rates.

Matthew then shares that he often gets friend-zoned on first dates, feeling too friendly and not flirty enough. Connell begins to address this by defining flirting as "play," but the response is cut off, ending with the host acknowledging the challenge and offering to continue the advice. The episode focuses on converting app matches into dates and adding romantic tension to in-person interactions.

FAQs

Send a personalized message about something she cares about, like her dog or a hobby, rather than asking her out directly. For example, ask a playful pop quiz question related to her interests to make her smile and re-engage.

Don't overthink it, but avoid early mornings when she's stressed. Afternoon or evening is generally better for asking her out, while playful messages like a coffee photo can work anytime to give value and engage.

Don't wait more than 24 to 48 hours. Women often have hundreds of matches, so staying on her mind with charming, value-giving messages prevents you from being forgotten.

Focus on playful banter and emotional engagement rather than just being nice. Use teasing or light challenges to create chemistry, and remember that flirting is about play, not just friendliness.

You may be coming off as too friendly without enough flirtation. Add playful, confident energy to dates by using humor, light teasing, or leading questions that create a spark, not just polite conversation.

Aim for about 8 total messages between you, or after one or two topics. Ask out sooner rather than later to show intentionality and avoid losing her interest.

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