Getting dates is great (yes!) What’s NOT great? Struggling with what to say, and dealing with long… awkward… silences (nooooo!) In this episode of the Dating Transformation Podcast, listen in on a coaching session that coach Connell has with his client Tom. Tom has gone from getting ZERO dates to landing as many as FIVE DATES a week! Just one problem: He’s still struggling with what to say and how to flirt. Listen now, as Connell gives some practical tips to avoid awkward silences and keep the conversation flowing and flirty. Plus: how to go for the first kiss!
"I take pride in being a great listener, allowing others to express themselves fully."
-Tom
"I value girls sharing their thoughts, it helps me listen & understand."
-Tom
"A genuine connection can be established by steering the conversation back on track, and women will genuinely appreciate your effort in doing so."
-Connell Barrett
Tom (Guest)
Connell Barrett (Host)
Founder and Executive Coach of Dating Transformation
Website: https://datingtransformation.com
Instagram: https://www.instagram.com/datingtransformation
FOR A FREE STRATEGY CALL WITH CONNELL, TO LEARN HOW TO
ALWAYS KNOW WHAT TO SAY TO WOMEN:
www.datingtransformation.com/contact
GET CONNELL’S NO. 1 BESTSELLING GUIDE FOR MEN, “DATING SUCKS
BUT YOU DON’T,” YOUR PRACTICAL GUIDE ON HOW TO GET A
GIRLFRIEND BY BEING RADICALLY AUTHENTIC:
https://www.amazon.com/Dating-Sucks-but-You-Dont-ebook/dp/B08LDZL3GX
00:27 Introduction
07:22 Navigating Fatigue and Enhancing Engagement on Dates
12:12 Conversational Tips: Avoiding Awkward Silences
22:15 Authenticity and Sincerity: Keeping the Conversation Real
24:45 Emotional Vulnerability: Overcoming the Fear of Opening Up
29:21 Taking Chances and Embracing Vulnerability
34:55 Charming Responses: Deflecting Personal Relationship Questions
43:44 Keeping the Date Focused on Each Other
49:27 From Lighthearted to Genuine: Building Deeper Connections
58:05 Geeky Banter and Smooth Date Requests: A Bumble Success Story
58:05 Building Emotional Connection: Before Asking for a Date
01:06:18 Outro
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Connell Barrett:
Welcome to the dating transformation podcast. Here's your host, dating coach, Conal Barrett.
Alright. Welcome back to the dating transformation podcast. I am your host, dating coach, Connell Barrett. I'm here to help you flirt with confidence, always know what to say, get dates and get a great girlfriend, and do it all by being authentic. And I love today's episode because Every so often on the podcast, I get to do a coaching call with a guy who is struggling with some things that you might have struggled with or be struggling with. And today, you're gonna be able to listen in on a genuine actual real coaching call with my client, Tom is an Australian gents. He's a great guy. And when Tom came to me, he was working with him for several weeks. And when Tom came to me, he had some really common problems. He wasn't getting very many quality dates. He'd had about a half dozen dates in the previous 6 months before talking with me. But only 2 or 3 of these dates were with women he was really genuinely feeling a connection with and attracted to. And none of these dates leading up to working with me had led to second dates. He was basically struggling to have good first dates. He'd also never kissed a girl. He was approaching 30, and he'd never so much as had a romantic kiss with a woman. So he was struggling with what to say on dates. He was struggling to get second dates and just get quality women to even show on dates with him. He was also struggling with matches on the dating apps. And I'm super psyched to say that a few weeks into working with me, He's done amazing. He's had his first ever kiss. He had to start somewhere, and he had a really great sexy awesome makeout with a really interesting woman. Young woman. And, also, he blew my mind a couple weeks ago because he'd shot me a text message and said, hey, Connell. Guess what? I have a busy week coming up. I have 5 first dates coming up. So Tom went from having 2 or 3 quality dates over 6 months to having a 5 date week recently. So he's done just amazing work with me. And what specifically you're about to hear is Tom and I working through some more advanced problems, So he's getting all these great dates with some really cool, wonderful girls. But he's having trouble knowing what to say. He's dealing with awkward silences on dates, and he's trying to make sure that there are no awkward silences on his first and second dates. And he's also not sure about how to flirt with women. Do I flirt a lot? Do I do the fun flirty moves? A lot? Do I do a lot of that? Which he's learned from me, or do I pull back on that and be more sincere, more vulnerable? And we talk about finding that right balance of how to be flirty, fun, making dates go well, but also how to be genuine and real. And be sincere and, of course, always authentic. So listen up. If you're struggling with awkward silences or if you're not sure how to flirt or what to say on dates, or you just want more dates to go better, listen up. I think you're gonna enjoy my conversation with my amazing client, Tom. I'm so proud of him. Listen right now and enjoy.
Connell Barrett:
I'm gonna read your mind. Ready? I'll bet that you would love to confidently approach women. Get great matches on the dating apps, flirt with charm, and attract your dream girlfriend. Right? But fear keeps you from approaching. You're not sure how to flirt. You struggle on the apps. And desirable women just don't seem into you. Well, I have great news. Dating coach, Connell Barrett, can help. He's guided thousands of men like you to more confidence and help them attract their dream girlfriends. So book a free strategy call today to see if Connell's coaching is right for you. On your call, Connell or a team member will give you personal life advice to help you have more confidence, more dates, and more fun. Oh, and you'll be dating women as your best self. A charming gentleman. That's because Connell does not teach creepy pickup artists tricks. He unlocks your most confident self. So you can make authentic, romantic connections. Your next steps? Book your free call today, updating transformation. Dot com forward slash contact and grab a time that works for you. Then you'll be on your way to more confidence, better -- and attracting bright, beautiful women. Oh, so you know, soon, Connell will stop taking on new clubs. So book a call today while you still can. Go to dating transformation dot com forward slash contact and transform your love life. Bye.
Connell Barrett:
Hey, Tom, Good morning. It's bright and early in Australia, isn't it? Hey, Connell. How are you doing? Good, man. Really good. How are things mister five dates in one week? Yeah. You must be tired.
Tom:
I am pretty tired, I have to say. Self-confidence. Introvert. And, yeah, I'd say it's quite energetically draining potentially because I'm still quite new to this. And I'm not really entirely sure of a lot of things. It's very new to me. But, yeah, it's all just an experience, and I'm kinda just taking it as it comes. Okay. Great, man. Yeah. Well, let's get into it. I can.
Connell Barrett:
Let's get into it. What kind of problems are you looking to fix today? How can I help you, man? Wanted to say their problems more just like question marks that I'd like to turn into. I don't know.
Tom:
Okay. Exclamation marks. Fire up. But, yeah, just for example one of the things that I do happens, well, I tend to be a better listener, more than a talker, unless people ask me really good questions.
Connell Barrett:
Sorry. What were you saying? I wasn't listening. Sorry. Sorry. I'm just kidding. Go ahead. Hello? Is this this thing on? Tough crowd.
Tom:
So this is exactly what happens on dates sometimes is, you know, I get thrown a curveball like that. No kidding. But, yeah, there are times when, you know, there are awkward silences during dates. I am just I. I don't know what to talk about, or she's run out of things to talk about, and then I'm just there going, okay. I could ask a question. But I kinda don't wanna turn it into too much of a question and answer type of thing either. That's a great question. Elaborate. Sometimes
Connell Barrett:
yeah. Can you elaborate? Maybe give me a specific example of this happening with a recent date.
Tom:
Yeah. I think, again, this sort of relates back to what we talked about earlier with me being tired on dates. I think it's just a thing with, you know, me not being used to it, but also just having a busy week or, you know, not getting a lot of sleep because I've, you know, stayed up late to do work or something like that. But there was one time when I showed up on a date, and it was really rushed. It was just a lot of last minute things that happened and I showed up on the date and I was really tired. I didn't feel like I had my usual bubbly energy kind of side of things. Like, I didn't feel like I could bring that to the table. And so throughout the day, I was kinda just acting as a listener and trying to keep my eyes open, not because she's boring, but because I was just tired. And She kept asking me questions, which I thought was great. You know, she didn't just give up and just go, oh, this guy's not asking me anything. And I was able to answer it. I did try not to, quote unquote, over perform and try to, like, you know, impress her with my answers. So I just tried to remain grounded. But I did feel at some points that, you know, I was when I ran out of things to say or you know, that there would be a little bit of an awkward silence. And during that time, I would feel a little uncomfortable or a little awkward. Just feeling like I, you know, I just have this thing in my head where I feel like I always have to be doing or saying something interesting. Or correct -- Got it. -- doing the right thing. You actually just
Connell Barrett:
mentioned the solution to your challenge and the problem within what you just said. Because the reason why people, quote, run out of things to say guys run out of things to say on dates, is because we make the bar too high for how good the things to say have to be, or we we turn it into something that's a performance. And performing is hard to do, but expressing genuine authentic thoughts, feelings, or asking genuine questions, you can never run out of that. So let me ask you a question. Mhmm. Have you run out of things to say in the last week with any of your good friends or people in your family? Have you ever just been talking to your mom, and all of a sudden, you're like, oh gosh. I don't know what to say to mom. I just ran out of things to say. Does that ever happen to you, or does it only happen on dates?
Tom:
Honestly, yeah. It does
Connell Barrett:
in general. Oh, really? You run out of things to say with your friends?
Tom:
Yeah. It could just be a AAA general underlying social anxiety thing potentially. Fair enough. Okay. But it also depends, I think, whether you've got me talking about something I'm passionate about or not as well. Okay. So maybe I'm a bit too nerdy. But if he asked me anything about personality tests or about business, I can probably keep talking for hours and hours and hours and hours. But I realized that's not necessarily, you know, panty dropping conversation. So
Connell Barrett:
By the way, panty dropping conversation is the name of my next book. So thank you for giving me the title. Appreciate that. Nice. Amazing. Cool. Or no. No. I shouldn't say. Cool. So you could potentially talk for hours and hours if it's the right topic or if it's something you're passionate about. Yeah? Mhmm. Okay. So That's one strategy you can apply on a date, if you aren't sure what to say about a certain topic, then change the topic to something you're very certain about, and that's hopefully reasonably engaging to you and to her. So for example, What are one or two topics that you could talk about for hours and hours if you had to?
Tom:
Personality tests. However, if I might add, I do find sometimes they get too passionate and too caught up in things. And I just, like, I'm just so excited to share this information, and I wanna, like, teach people that I can sometimes I find myself overtaking the conversation, and I end up talking too much, and I don't get the girl to actually talk about herself.
Connell Barrett:
And -- Well, let's tackle one problem at a time. Because you're rebounding from, I don't know what to say, two, and then I say too much.
Tom:
Yeah. So I kind of swing at this pendulum from extreme to extreme sometimes. Like, a wrecking ball, I guess. Yeah. Anyway -- You're right. You're
Connell Barrett:
right wing ball. Okay. Very cool. Please continue. Well, let's solve the first challenge first. Basically, running out of things to say. Here's my advice for you in terms of running out of things to say. Strategy number one is to have a back pocket topic that you can go to. And if you find yourself literally thinking, oh, gosh. I don't know what to say next. I don't have an opinion about her ski trip to Vale, Colorado or whatever you're talking about. I've never skied. I've never done a thing that we're talking about. Have a back pocket topic, and be ready to use that at a moment's notice. And you might say, oh, hey. By the way, before I forget, Angela, was meaning to ask you, have you ever taken a personality test? They're really fun. And then you can start talking about the personality tests if that's something that is interesting to you. Because so much about creating a really good spark and, quote, unquote, attraction on a date is that you're transferring your good positive passionate feelings onto her. Women wanna -- Mhmm. -- catch the good feelings. So I'd love for you to talk about something you're passionate about because if you're passionate about it, you're gonna be into it, excited about it, and that can rub off on her. Plus, you're talking about something you know a lot about So I'm gonna give you a two part tip here and then hit me with any questions. So the back pocket topic is one thing. The second back pocket move to have going I'm talking about going into a date is a back pocket question. Something that you tell yourself, okay. I'm gonna ask her this question if at any point tonight I get in my head about what to say. And you can just write something out literally or figuratively, and have a back pocket question you wanna ask. So for example, let's say you look at her profile one last time before you walk into the bar. And you see, oh, okay. She talks about how she loves Jonah Hill movies. Judd A Patel movies, for example. Yeah. Then you can say, if I get stuck in my head at any point, I'm gonna ask her Hey. I'm curious. What's your favorite Judd Apatow movie and why? And then all of a sudden, you have something to talk about. So if nothing else, you can avoid those awkward silences because we do want to avoid those. So a back pocket topic that you're into or a back pocket question, that you're interested in asking her. And you can use these sort of as a safety net if you do get stuck in your head. Does that make sense, bro? Mhmm. Yeah. Questions, thoughts, epithets, follow ups.
Tom:
Yeah. I mean, there's like there's a question that sort of popped up in my head. I've sort of half answered it myself, and I might as well vocalize it. And that's you know, I think it's more of a scenario of the first date. That makes a lot of sense. And it could be the same thing as well with a second date as well. I did find that on a second date, I didn't have as much to ask either. There's a little like, I know her a little bit more, Potentially, I wasn't too focused on getting too deep as well. And I was just more focused on trying to, you know, be playful and sort of have that interaction, that flirty fun. Okay. Yeah. I don't really know where I'm going with this. But, yeah, I did find that in terms of the activity too, I found that Oh, actually, that's it. So, you know, when I'm sitting down, having a sit down date, which is usually what the first date is, at least an initial part of it, getting to know you, you know, have established that baseline rapport, I think it's much easier. To sort of, like, get into that conversational mode and listening mode. I think it's more for example, when I'm on a date and it's more of a AAA fun sort of thing and like an activity like bowling or arcade games and that sort of thing. That's when I'm like, okay. Well, this probably isn't the time to be talking as much, like, in this kind of way. And that's kinda like in my head sometimes where I I feel like, should I actually have a sit down with them first? Before we move to an activity, even if it is a second date. Because that's actually what happened recently as well. I went on a second date. One of the -- Okay. First, actually, that we've ever gone on. And with the five that you mentioned, actually. And, yeah, we went straight into games, and it felt a little bit weird for me.
Connell Barrett:
When you say games, what do you mean?
Tom:
Straight into bowling, turns to arcade, shredded to pull billions. What was your first date with you? What was your first date with her? What did you do? You sat down at a bar for half an hour, then we went for a walk around yeah. Sound.
Connell Barrett:
Okay. And then the second date was the activity date. Yep. Okay. Got it. So what's your question? Is it why it feels weird, awkward? Why -- No. Like, basically,
Tom:
like, conversation wise, it wasn't the same sort of, like, connective type, getting to know you type -- Yeah. -- feel. I'm pretty new to this, so it feels weird to me. A lot of things feel foreign to me, especially the activity date. And so, yeah, the activity date just is okay to not, you know, talk? Is it okay to know? Like, what's the
Connell Barrett:
What was the activity again?
Tom:
It's a bowling arcade.
Connell Barrett:
Okay. Alright. Bowling and arcade. So what
Tom:
what you were talking at least a little bit about, oh, it's your it's your ball it's your role now. Right? Yeah. So there's a little bit of, like, oh, you know, hey. It's my I was like, oh, wait. Like, get out of my way. Like, you know, just, like, a lot of like, a few playful things here and there. You know, hey. It's my turn. No. You're still on my board. What are you doing? You know? This kind of thing, which is fine. Like, admittedly, I just felt like, you know, should I have included or tried to include a little bit of that? You know, face to face talking interaction.
Connell Barrett:
So it was a two basically, it's a two part date. It was bowling and then arcade, and then that was it. The end of the day? Maybe, like, four parts, actually.
Tom:
So bowling, arcade, Billiards, is that what you guys call it? Okay. Yeah. Yeah. And then we went to get some fried chicken and ice cream.
Connell Barrett:
Okay. And then during the fried chicken and ice cream, wow, a four part date. Damn. That's awesome. That's great. So during the chicken and ice cream, did you get a little bit of time to talk more one on one about each other as opposed to about the activities?
Tom:
I guess so. Like, she was more talking to me, which I I mean, I love, actually. I love it when girls just keep talking because then I don't have to talk. And Okay. Yeah. And, yeah, there's a little bit of, like, you know, silliness in between, but I never really revealed anything much about myself, and I never really after too much either. I don't know. I think again, it comes back to your original point. I think I was putting too much pressure on the tape. Was thinking, well, how can I escalate this? How can I blah blah? And I was sort of caught up in that mentality.
Connell Barrett:
Not okay. Great. Great. Great. I'm so glad you said that. Forget escalations. Okay? I'm not saying don't worry about it ever. I'm saying don't think about that. Women don't wanna go out with a guy and have him escalate on her. Women wanna go out with a guy and feel like, woah, he really sees Well, first, I'm having fun with him. Secondly, he is learning about the real me, and he likes me. Hopefully. And I'm learning about the real authentic him, and I like him. And so what you might call, quote, unquote, escalation, it'll happen very much organically, or at least a lot of it will, as long as you're being increasingly transparent vulnerable getting to know each other through conversation while also having a little bit of fun, or maybe a lot of fun as the date might progress. Does that make sense? Before I go more specific about how to do that, does that make sense?
Tom:
Yeah. Be present, I think, is what you're trying to say.
Connell Barrett:
Be shown her the real you. Open up a bit. And here's a good way to think about it. One of my old coaches said this to me, and I really liked it. And I still use it sometimes, or I give this advice to a client like you. Find out what makes her fascinating. So this bowling girl date, bowling billiard, arcade and all the other things you did on this twenty seven hour date, I assume. What did you find out about her that is fascinating or interesting to you, if anything?
Tom:
I haven't taught her this, but she's quite young, and she studies full time. Works full time as well and basically supports herself all in Iran at a very young age, actually. Okay. So I'm very impressed with that. I'd like to know how I don't know if she does it, how she survives.
Connell Barrett:
And -- So what -- so keeps it going, I guess. Yeah. So what you just said about her to me I want you to say that to her. Sure. Say those kinds of things on a date. Literally, the words you just used, simple language, nothing fancy, be able to say to a woman, hey, by the way, I just wanna say, I think it's incredibly impressive. And so cool and impressive that you are independent, so together with it at such a young age. Yeah. I'm not easily impressed, but, damn, that's really cool. Tell me, how did you get that way? I mean, that's the kind of vulnerability and sincerity, authenticity, call it, which you will, that you want to bring to a date After the fun, after the, hey. Nice to meet you. Little bit of flirting. Fun bowling. Get to know you chit chat. Basically, the fun stuff. We wanna open up a little bit and be really real. And give her the gift of saying, hey. I see something in you that I really like. And I'm impressed by it. Tell me more about it. And then at the same time, she's also looking for you. Sorry. She's also you're you're by going first using that law of reciprocation, you go first. A woman is more likely to follow suit and say, Well, I'm glad you said that because, Tom, you know what I really like about you? I like XYZ. She might offer that to you, and now you've got two people who are really being more emotionally naked, emotionally vulnerable. Now you don't do that in the first ten minutes of a date, but you absolutely can do it on the second half of a first date and no later than during the second date at some point. Does that make sense?
Tom:
No later than it's oh, okay.
Connell Barrett:
Yeah. Never later than the second day. You want to be increasingly real and transparent over the course of those first one or two dates. So the game if a game is fun flirting what I call man to woman moves. That's all fun in games. That's, like, frosting that's, like, frosting on a cake. It makes the Tom cake taste better. But what she really wants is a slice of the cake, meaning the real you, the honest, you the, hey. I'm really impressed by you because XYZ reason if that's how you feel.
Tom:
Mhmm. Thoughts, questions about this. Makes a ton of sense. I guess, you know, there's a part of me, and I think a lot of people can relate to this. Sorry. Excuse me. No worries. Pardon me, that is I guess, yeah, because it's new to me as well. You know, it feels a little uncomfortable with opening up emotionally. I think just because, you know, in the past, I've been off emotionally really quickly, and it's been really scary or it's backfired or whatever. You know? And I'm sure this time around, things are a little bit different because I'm coming from a different mentality. But there's still that underlying fear, I guess you could say, that I, you know, don't wanna get too . I do find myself holding myself back with the emotional stuff. Okay. So I remember there was one time when I went on a sec Kinn's date with a different girl. And she started talking about her parents and asking me about my family and that sort of thing. And I don't normally like to get into that sort of stuff because it can turn me very, very, very vulnerable. So I kind of, like, got a little bit annoyed, and I was like, I don't really wanna talk about this. I think yeah. Because there's that underlying fee. So that's kinda like what comes up when you bring that out.
Connell Barrett:
Fair enough. Well, you want to show her layers of you. Now, you have to choose how deep you wanna go, Mhmm. And you can I want you to, within reason, protect yourself from being too emotionally vulnerable too soon? But you still wanna let some of those cracks of light shine through, whatever that might help. I'm not again, I don't know your whole history. I'm not saying you have to have deep, tear jerking conversations about powerful, painful moments from your past. But it's it's it it can be as simple as showing some, sharing some specifics about you. Some moments from your past or thoughts and feelings or fears you have? Like, for example, I have a girlfriend now. My partner, Jess, is my partner. However, the last time I was out dating in the world, I remember I was on a first date with a woman. And it came up organically, but all of a sudden, 45 minutes an hour into the date, I found myself talking about my my 9 week failed marriage from a million years ago, and how my during my honeymoon period, during these 9 weeks that the woman I had married, she essentially was cheating on me with a guy who had a cool mustache and a cool motorcycle. And I was talking about how painful that was at the time
Book Intro:
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Connell Barrett:
But through the lens of, oh, I learned some valuable lessons. I learned how important it is to take chances, and I'm so much different than I was then. So I didn't do that as a move with her per se, but I was willing to get vulnerable, at least briefly. I'm not saying you have to be vulnerable. But if you do want to even if it's not even if it's uncomfortable, you want to have the courage, maybe is the right word, to be able to say, okay. I'm gonna show her a little bit more of myself because that's basically who she's deciding on dating. If she can't see the real you, then why would she wanna date the real you? You're just a guy that she's playing cool with. So the fun in games part of it, the frosting, is very important. We wanna give a great top layer of frosting, but let her taste that cake. The cake of -- Mhmm. -- the cake of Tom. The cake that is Tom. The cake. I like it. Yeah. Before I forget, I wanna give you a tip that you can put to use immediately. This is great to do on first dates. The great thing to do on a first date is look for a moment during the date before it's over, obviously. Look for something that you specifically really like and appreciate about her, something you find attractive. It can be something you find sexy. It can be something you just find really a cool attribute that you find interesting or different and let her know that you see it. So for example, on my first date with my now girlfriend, Jessamine, I remember we're on the rooftop of my apartment building. We'd gone to a couple locations, and then she came back, and we were having a glass of wine on my rooftop. And I was just so blown away by her wit. She's very witty. Quick witted. And I was just pleasantly surprised by that. And I said to her, pretty much verbatim quote, I said, Hey. I just wanted you to know that you are the wittiest, funniest girl I think maybe I've ever had a date with. I knew you were cute and pretty, I said to her, from your profile, but, man, you are quick with it. I'm just trying to keep up with you. And I'm not easily impressed. And I just put it out there, a very vulnerable, sincere, specific compliment. And she smiled and said, oh, well, thank you. But later, she told me that that basically really melted her, which was my hope in part. Wasn't it? It wasn't just the move. It was really just that I wanted to express my genuine true feelings. But also, I wanted her to just I wanted that to land if that resonated with her. So something you could do going forward, and this is how we stay out of that, quote, unquote, friend zone or how we create those emotional connections is taking having conversations, being really present with the woman, and notice something specifically about her that you find sexy, cool, interesting, different. And then just telling her, putting it out there, and letting her receive it and see how it feels for you and her. And that's a really good way to spark some real genuine emotional connection or to tell a woman she's really cool and interesting to you and sexy. Mhmm. Might be a little scary? But that's something that I want you to get increasingly comfortable doing. How's that sound? Yeah. For sure.
Tom:
Sounds good. I guess it's eventually, she has to know the real me. So I guess yeah. Yeah. Just got it on the net. Quick side question related to that -- Yeah. -- to take on that, which is if she asks deeper and I'm not comfortable going deeper, is it okay to say you know what? Let's not talk about that right now. Or will that kill all? Like --
Connell Barrett:
Yes and no. Let me answer you in a hopefully nuanced way. It depends on what the topic is. And you do it well, can you give me an example? The recent date you've had of topics -- Sure. Let's Okay. Well, one of my first dates,
Tom:
she asked, are you close to your parents? I think we can assess from what I've said so far that I'm not. Okay. And so I generally don't like to talk about that. Okay. So, yeah, to that.
Connell Barrett:
Okay. I would be aware of shutting her down. Basically, a no comment can create a block to a connection. There's a way you can say that, or there's a way you can deflect without making her feel shut down, but also without maybe you just don't wanna talk about your parents on a first date, which if that's an issue for you, I totally respect that. And honor that. So what you can do is be a little bit of a politician. Politicians have this skill of -- Mhmm. -- basically responding to a question, but not actually answering. Without responding to it. Yeah. Yeah. Right? Like, you're a very articulate witty guy. So you might you might
Tom:
stay The ticket just mounted.
Connell Barrett:
You might. I am so attractive. I attract men. I attract women. I can't help it. No. I really mean that. So you don't want her to feel like you're shutting her down, but you also might not be ready to talk about your challenging relationship with your parents. Which I totally respect. So what you can do is basically respond but deflect with a little smile or a little charm or a little topic change. So for example, if a woman asked me that on a first date and I just don't wanna talk about it, then I mean, gosh. I'm trying to think of this. Let's be like, I'm okay with talking about my failed marriage from my youth, but let's say for whatever reason I didn't want to. Right? Let's say I just felt like this is really not the time and place to talk about this. I would try to respond to her and maybe crack a joke and you have an ample great sense of humor, maybe crack a joke and respond, but then deflect to a topic or deflect to a AAA related topic, but that doesn't make her feel like you're avoiding it. Well, here's an example. Because I'm a dating coach, the last round of me being single going out on dates, women love talking about me being a dating coach. However, that's not a really great topic because it's a little bit too meta. Talking about dating is not necessarily a fun topic. So what I do is I say, oh, yeah. I've got a crazy job. I love it. I'm basically the real life hitch because dating is just crazy. And, like, I'll bet you have some crazy first date horror stories, don't you, Jenny? And what I'm doing is pinging the conversation back to a really good topic, which is first date, crazy weirdo, first date horror -- stories that a woman has from other guys is actually a really good topic for a first date because every every woman's got these stories. And then -- you can talk about oh, sorry. And then subconsciously, she's comparing the awesomeness that is Tom, to the weirdo guy who his cocaine dealer showed up on his first date with her and freaked her out, which is a true story from a woman I met. And so, basically, what I'm doing is I'm trying to redirect a conversation to something that I think is good for the date. And also, but doesn't make her feel like I shut her down. Right? So back to your question. If a woman said to you, oh, hey. Are you close to your parents? Instead of saying I don't wanna talk about that, which would make her feel, you know, a little bit almost like conversationally rejected. Even though you wouldn't do it that way, she might feel that way. You wanna keep the good vibes going. So what you could say is, oh, well, you know what? I have a I have you know, families are crazy. I have a fascinating complex relationship with my family. And you might then change the topic. Keep the topic to family. But then maybe share a detail about family or about her family so that you're not saying no. You're saying, oh, man. My parents are crazy. Alright. Everybody's parents' crazy? Like, what about you? Are you closer to your mom and your dad? And all of a sudden, you're talking about her mom and dad. So it doesn't feel like you shut the conversation down, but you've deflected it away from you talking about your family. Does that make sense?
Tom:
Yeah. And, hopefully, she gets the hint.
Connell Barrett:
Right. So you have to be a little bit of a you can be a little bit of a politician. This brings up an actually, on a larger point, that is kind of an advanced dating move, but you're you're ready now because you're getting multiple dates of the week, some weeks. And -- Mhmm. -- and I know you and I have texted about this is I want you or any guy to take responsibility for keeping conversation topics on topics or areas that serve your date. It's kind of like there's a little bit of an editor or a producer -- Mhmm. -- who's always kinda monitoring the date. Mhmm. Thinking to yourself, is this is this good for the date or bad for the date? Is this is this fun or not fun? Is it helpful or not helpful? And And so, yeah, if the topic is oh, gosh. She's asking about my parents. I really don't wanna go there. Not good for the date because you don't wanna go there. So you can then deflect. Or, actually, you could all hear oh, let me give you a tip. You could you don't need to literally do this with me right now because I don't want you to reveal your parents' first names, but you could play a fun game with a girl called called Who's let's find out whose whose dad has a better dad name. So for example, if a if a woman said, hey, Connell. Tell me about your parents. Let's say I didn't wanna talk about it for some reason, I might say, oh, man. My parents are my parents are one of a kind. By the way, that reminds you of a fun game. Let's play who's got a dorky or dad name. And I ask her her dad's name. My dad's first name is Dennis. Hi, dad, if you're out there. Denny, Dennis, which is kind of a dorky nerdy name. And then she might reveal her dad's name is, I don't know, Elliott I'd say, okay. You win. You have the dork of your dad named it me. Damn it. I thought I had you there. So we've kept it on the topic of parents But instead of heavy duty, maybe emotional stuff you're not ready for, it's a fun little dad name game. Yeah. And that's good. So you would like to deflect. Now I don't do it a lot, but if I I like to I was on a first date once with a girl who could not stop talking about her ex boyfriend. Oh my freaking god. It was ex-boyfriend this, ex-boyfriend that.
Tom:
And annoying, actually. Yeah.
Connell Barrett:
Two or Three I kept redirecting things back to us, to things that were fun and good to talk about for us. And she finally I mean and she but she kept going back to him. And finally, I just and you can do this after if you if a woman keeps the topic, keeps changing topic to something that doesn't serve you, you can straight up say what I said to this woman, which was, hey. I totally respect that you are talking about you and your ex, but I'm on a date with you tonight, and I want you to be on a date with me. So how about you and I come up with a rule? No talking about our x's. Are you down? High five. Let's shake on it. Let's fist bump on it. And she got the hint and basically appreciated that I I took responsibility for fun, good first date topics. So worst case scenario, if you try to redirect a few times and she keeps pressing on the family thing, you could say what? To be honest, I don't feel super comfortable about talking about that. But I totally get why you asked, and it's all good, maybe for a second date. And then Sometimes just laying down -- Yeah. -- sort of your boundary is a way to show that strength and steel that women are looking for in a guy.
Tom:
Yeah. Yeah. I think there's definitely a bit of courage there as well. I do it, yeah. Did you kinda, like, remind me of a Again, it was a second date with some other girl. But she started talking a lot about her mom, and it kinda got a little deep on her end, and I was just being a really good listener. I think that's one of the traps. Actually sometimes I'm too good of a listener, and I just don't wanna interrupt her. I don't wanna stop her emotional spillage, whatever you call it. And so I go, oh, I could redirect, but would that context be really inappropriate right now. You know? So just you know what? The tap's running. I'm just gonna let it run itself out. But then it goes on for really long. And, yeah, I feel the energy of the date sort of just thrives off a cliff. What was
Connell Barrett:
again, you don't need to reveal specific details to identify her. But was she talking about her mom in a, like, a negative sense or or, like, a was it bringing more positivity
Tom:
or more negativity at the table? I think it was more. I think it was more. It was more of both. It was more okay. Well, I wasn't close to my mom before. And then, you know, I tried x. I tried y. I tried zed. Didn't work. And so, you know, I just yeah. Whatever. And then eventually, over time, she is she we've gotten closer and
Connell Barrett:
yeah. So this is her talking about her mom. Mhmm. Okay. Yeah. For how long? Did she talk about her mom roughly? Like, 15 minutes at least. Oh, okay. That's a lot. Like, 10 minutes. -- about other people. By the way -- I said, Luke, Okay. I mean, let's come back to some real basics here. We don't always, but almost always wanna keep the dates about you, about her, and how you 2 sorta connect commonalities, things you have in common with emotions. And it's also totally great to also talk a little bit about family members. So her mom is obviously important to her. Right? Mhmm. Fine. Totally fine to talk about those things. On my first date with my now girlfriend, Jess, she talked quite a bit, not quite a bit. She talked for a little bit about how she's really close to her brother. She talked about a car accident she had with her brother once, how scary it was. She talked about her mom and dad. And so it's totally fine to talk about the circle of trust that a woman has in her life. It's good actually to ask about her. Family and those things because that shows that you're showing interest. At the same time, if I had to put a time limit on it, I would just kinda wanna monitor that, hey. Are we talking about other people too much and not about each other? Because you wanna bring it back to Tom and Jane Doe. And 15 minutes about Jane Doe's mom is a long time to talk about somebody else. Maybe just a couple couple minutes about mom or dad. So, again -- Okay. Yeah. -- there's that editor, there's that producer who's always sort of monitoring the conversation. Just like Matt, the podcast producer, is monitoring this. It's kinda like you wanna monitor the date and say, hey. She's been talking about her mom for 15 minutes. Maybe it's time to again shift to a different topic, something that's a bit more date conducive to a nice, flirty, sparks flying, fun connected date because that's what we really want here. Yeah. So for example, quick example, I was on again, I go back to my last round of being single. I had a date with a woman, honestly, with a woman. As I had a first date, she was talking about med school. She'd gone to med school, and she had a bad experience. And she was getting pretty negative. And I listened to that for a couple minutes. And in the back of my mind, I'm thinking, okay. I I totally respect that she struggled with med school, didn't like it, but she was getting really kinda negative about it. And it was bringing her down, which was bringing her date down. And so I made a little note to myself because she had mentioned something else. She had mentioned a funny story that happened to her in Italy, on a trip to Europe earlier, and I and I made a mental note. Funny Italy stories, way better than why I hated meds. School stories. Right? Uh-huh. It's a much better date friendly conversation topic. So I let her vent a little bit about med school sucking. But then I said, oh, hey. By the way, before I forget, Jessica, whatever her name was, remind me, tell me that story about Italy. Because that sounded amazing. You said you said something about getting lost in Rome and a story about this and that, and her face lit up. When I switched the topic. Mhmm. And she just enjoyed telling that story a lot more than she enjoyed talking about med school. So, yeah, it's a first date. It's not a therapy session for her. Mhmm. If you or she find yourself talking about someone else almost in a therapeutic way, come back to this idea of, hey. I'm a man. She's a woman. This is about a first date where hopefully, some romantic sparks can fly. A genuine connection can happen and try to steer things back. And women will actually appreciate you doing that.
Tom:
Well, on that note, actually, so we've been talking a lot about Thursday sort of context, which, in my opinion, hundred percent, Keep it fun, light, playful, flirty, enjoyable so that you get the second day. At which point, is it okay to go into more of that sort of talk?
Connell Barrett:
The more, like, vulnerable talk?
Tom:
Mhmm. Yeah.
Connell Barrett:
At twenty seven minutes and fourteen seconds in.
Tom:
That's the exact time. Write that down. Oh, off to the second date?
Connell Barrett:
On the first date, if it's a Tuesday. But if it's a Thursday, It's a different time.
Tom:
So do the time zones play a factor too? What about when Mercury's in Metrogate and, you know, The planets are aligned, and there's a solar eclipse.
Connell Barrett:
What about that? Yes. And if Haley's comet is in the sky, then you wanna add 7 divided by 4. Uh-huh. No. Great great question. Think Let's think let's think of 2 modes of communication. As you know, 1 of the big things I teach, guys, I work with, like, your good self is manda woman communication. Right? Mando woman communication is basically the quick CliffsNotes version that It's about good emotions. It's flirting. It's fun. It's light. It's good emotions. So think of there being 2 modes on a date, man to woman. And then sincere slash real.
Tom:
K? Okay.
Connell Barrett:
At the beginning of the date, the first half roughly, you're gonna have more, quote, unquote, man to woman, spiky, fun shtick, basically, flirting, teasing, joking, lightning, As the date proceeds, that imagine, like, an x y graph. Like, this and the graph goes up from man to woman early, it's gonna increasingly go down. Own as the time progresses on the date over an hour or 2. And what's gonna go up is the real, sincere line. So, basically, you kinda drop much of the gamey fun teasing, jokey, flirty stuff, and just kinda be more real with each other. So, again, I'll use my first date with my now girlfriend, Jess, as an example. I remember our first date vividly because it went so well, and I was so into her. 01/20/3040 minutes, we were just cracking a lot of jokes. Just teasing, joking, I accused her of being a stalker. She accused me of being a sketchy pickup artist, you know, in -- Mhmm. -- in a good natured way. Just a lot of very light fun stuff, just silly light, and some flirting too. As the date went on, that's when she started talking about, oh, yeah. My brother and I were in this car accident. It was so scary. I shared with her about my failed marriage. How I became a dating coach, how I used to be so introverted and nerdy and insecure. And then, yes, it was the further the date went on, the more real and sincere we got. Now we can always come back to jokes and teasing or or whatever your mode of flirting is. But, basically, think man to woman more early and then more sincere and real as the date goes on. Would you say that you're being relatable?
Tom:
Would you say that's the recipe for, like, a better word? Would you say that's a recipe for every date, not just the first date, the second date as well, third date, fourth date?
Connell Barrett:
For every date,
Tom:
bit of mantle on the start and then Not necessarily. Because I do find myself I do find myself feeling that. Because it's like, oh, it works on the first date. Surely, I should do the same on the second day. Or, you know -- Okay. -- sometimes I find, you know, the second day is like, oh, I kinda already know a lot about her. Probably not don't have everything yet, but it does feel like, oh, it's becoming normal. And there's a part of me that's like, I don't know. It's becoming too normal. You know?
Connell Barrett:
Yeah. You're asking me a great question. No one's ever asked me that before. Yeah. I reserve the right to change my answer here, but my gut says yes to what you said. Early on in the day. Like, you're not if it's the third if it's the third date, early a little bit of lightness getting some rapport back early and then increasingly more real as the date goes on. Yeah. I would say that they're very similar on dates one, two, and three. The difference is you can have increasing levels of rapport and comfort with each other because you have gotten to know each other over the course of several get togethers. And you can essentially get yeah. Then you can get a bit more real and vulnerable. As opposed to if you're
Tom:
Three feet deep on the first date in terms of realness, you might be seven right or ten feet deep. On the third day. Because there's always this niggling yeah. There's always this niggling sort of, like, question or question mark in the back of my head where it's like, oh, is it that we are connecting too much now? Are we going to become too much of a friend? And there's no more of that. You know? Match a woman sort of thing. Dynamic. I think there's always that question in my head.
Connell Barrett:
That's the second and great -- It's on what -- -- great question because we want to be friendly, but we don't want to be friend zoned, obviously. Mhmm. So I think of it like this. Think of as long as the romantic, here's that word again, escalation. As long as the two of you are escalating mutually, organically relatively, but mutually over the course of one, two, or three dates, don't worry about, oh, am I getting friend zoned? What I mean is because you always wanna be circling the bases even if it's slowly, the bases being an emotional vulnerability, physical escalation, just more and more personal. We always wanna be circling the bases. So as long as that girl feels like, oh, wow. I'm really getting to know him better. And we're still flirting. And maybe you're a bit, maybe you're a little bit more bold and flirtatious on the second or third date than the first date. Right? Maybe on the first date, you say, oh my god. You're so cute. I'm so glad I met you. And on the third date, you look at her with You are so fucking cute. I'm sorry. You are sexy as hell. Damn. You look amazing tonight. You might escalate that up just because you're now more comfortable with yourself. So as long as we're constantly you know, in a win-win, mutual way, you're dialing those sparks up together and escalating them in a mutual way, you're gonna be fine. You don't have to worry about getting, quote, friend zone as long as it's -- It keeps per because women like the feeling of, oh, this is this is moving towards something. This is progressing. We're not we're not staying stuck and having it on the first date over and over again.
Tom:
Yeah. I feel so happy, you're gonna say. No. I think that answers my question. Thank you for diving into that. Sure. Yeah. Which is I yeah. I'm afraid of becoming friends again because I'm such a good connected type of person. Since he is authentic. I think a lot of guys are like this too. That you know, I'm afraid that if I go too deep into it, yeah, I'll just end up where I was when I first started.
Connell Barrett:
Well, you don't want to Don't don't think, oh, being emotionally vulnerable leads to the friend zone.
Tom:
Is that what you feel like, oh, if I'm being too Sometimes. Yeah. Because I've always been that therapy friend, if that makes sense. I've always been the guy that's really good at understanding and asking deep questions and relating and -- Right. -- that sort of stuff. And so I find myself being cautious about getting into that mode -- Okay. -- for that reason.
Connell Barrett:
Gotcha. Yeah. Well, on dates, stay out of therapy mode. Right? Stay out of it and don't be her best therapy friend. Don't be her best gay friend. Don't be a girlfriend. Be a man. By which, I mean, you can be sensitive and you can listen. At the same time, you also wanna let her know she's sexy. You wanna let her know You're attractive to her if you are. You wanna make her feel like, hey. I'm a masculine authentic force putting my energy out there. And letting her feel that authentic masculine sense of view and letting her be the feminine force receiving you. Now I can talk about this in my book. You might remember. There are brushstrokes of the, quote, unquote, feminine. Totally to listen, totally fine to be a little bit sensitive. But at the same time, that's what she has her therapist for, at least early on. That's what she has her girlfriends for. Your man is on a date with a woman, and we don't wanna lose sight of that overarching frame.
Tom:
A hundred percent. So yeah. Yeah. IIIII feels that. I feel that. Admittedly, as the date goes on and my intro batteries run out, slightly run out. Yeah. I I find that more difficult to maintain that mindset, but I guess it's just practice. At this point for me. Just go through practicing until it becomes ingrained. Yeah.
Connell Barrett:
Yeah. Absolutely. Last question. I mean, I wanna give you a chance for one last question in the time we have here. What other dating question slash child slash problem do you wanna help with? Let's finish strong, Brooke.
Tom:
I feel like we might go too deep into it. I didn't expect that many follow-up questions to this, actually. The first question that I had. Well, you know, let's talk about potentially something a bit more simple.
Connell Barrett:
Okay.
Tom:
So I matched with a girl about two weeks ago on Bumble. And we really hit it off. She's really into Dungeons and Dragons games and that sort of stuff. Pretty much a very geeky kinda go. And I'm into that sort of stuff. So In my opinion, I was very smooth with the Dungeons and Run Dungeons and Dragons related banter. So how did she start working? Because, you know, the Bumble deal starts. She guessed my two truths won't lie, and I basically made a whole bunch of jokes about how she failed her diced roll and because she got it completely wrong. So that sort of thing. And, yeah, it was a lot of good back and forth, long paragraphs, high indicators of interests. And, yeah, I decided to ask her out in a really cool way. I thought this was really cool. I am really proud of myself doing this. How did you do it? So, basically, let me explain it. Story mode. So Yeah. So I think she 's talking about games that we play, what kind of games you play, blah blah blah. And then she asked me what games I play. He's like, oh, you know, a bit of role playing games, RPGs, some adventure games, some action games. But this game that I'm really, really, like, you know, keen and excited to try out, and she totally fell for debate. Oh, what kinda game do you like? Are you looking forward to fighting? And I'm like, oh, yeah. It's called organizing a date with a cute Dungeon Master Girl on Dun on Bumble. It's a two player game, cooperative, and I could really use some help. Are you game? And yeah. I like it. She was great. She was like, oh, I hear the game's got really good graphics. You know, realistic. But the story can get a little, you know, crap sometimes. I was like, whatever. So then I asked for the number, and she was like, oh, I'm not very comfortable with that. But here's my Instagram or -- Okay.
Connell Barrett:
-- whatever.
Tom:
Which I'm not a huge fan of, but, you know, I take what I can get. Go to Instagram, try to arrange a date, And then she goes, oh, I'm really busy, actually. Like, the next couple of weekends, I'm going on all these conventions because it's convention season, and she's doing cosplay and that sort of stuff. Which I think, yeah, that's really cool. Like, she does actually create certain costumes and all this sort of stuff, like, in you know, she's a dungeon master as well. Has some podcasts related to games and that sort of thing, which I think is really cool. So I'm really curious and I'd like to get to know her, but it's just been difficult because she's just unavailable. Say, hey. You know what? Maybe next week, like, on a week night or something. I'll get back to you on a weekend. And I misread that as, oh, I can ask her out next week. So I said, how about this day or this day. She goes, oh, no. That's not what I meant. What I meant was I'll I'll get back to you after those days. I was like, okay. So it's a whole week. And then I didn't really check-in with her throughout the time. I didn't keep up the engagement. It's just I don't really go on Instagram, so it's a bit difficult for me to to jump on. And sometimes I feel a bit weird if, you know, I'm potentially stalking her a little bit with her stories and trying to ask her questions about that. Because I also didn't wanna become a texting buddy, and I didn't wanna ask all these questions before the day either. I wanted to connect in person. Right. So fast forward a week, I asked her again. She goes, No. Like, I've got something else coming up. I might need to get back to you on this thing. And, yeah, she hasn't. Got it back to me. But I do feel like I'm asking a lot of, like, hey. Are you are you free yet? Are you free yet? Are you free yet? And it feels I don't like it, basically.
Connell Barrett:
Yeah. So it sounds like you're mainly asking for dates. She says, I'll get back to you. Then you ask, then she'll get back to you. Right?
Tom:
Yep. So the conversation's gonna die with it. And Yeah. So I'd like to know, is this something I can -- Yeah. -- revive?
Connell Barrett:
Basically. So here's your forward texting system that you wanna follow in general. I don't know if you wanna continue with her. Because she's not giving you the kind of interest. I'm sorry. She's giving you interest. She's not getting to a decision. Right? She's kicking the tires. She's kicking the Tom tires, but she's not saying, let's take Tom for a test ride. Right? And To an extent, we want a girl who's like, hell, yeah. Let's go for a ride. Anyway, but here's the system you wanna use, and you're not currently doing this. So let me point this out to you because this will really help. Yeah. Here's the four word texting system. Here's how we text women. Give.
Tom:
Give. Give
Connell Barrett:
and then ask. Right? You know that. And you did it first. Right? You gave it first. In other words, what I mean by give give give ask is most of our messages should be giving women good emotions, jokes, funny memes, good questions. Basically, you're making her feel good. In other words, you're not asking for anything right away. And then when you ask for what you want. And, hopefully, you get a date. But if you don't, if she says, well, I'm really busy. Things are crazy for me. Then you go back to give, give, give. If you're so inclined and so motivated. What you don't do is just go quiet and then ask every once a week. Because then you become that annoying email marketer who's like, so are you ready to invest in making money from home or not? As opposed to somebody's actually giving you something. So -- Yeah. -- if you and there's a balance here. I'm not saying you give a message. You text a woman forever. But if she basically says, hey. I can't do it right now. Crazy, busy, cosplay, whatever. Ben, assuming you're genuinely interested in her, then you go back to, within reason, giving. Cups, two or three text messages over the course of the week, maybe a fun update on your life, a fun teasing joking question. Hey, miss Cosplay. Let me guess. Right now, you're dressed up as the drag, you know, which dragon which KALICI which of KHALEESI's Dragon are you just talking about right now? I don't know. You're basically making her laugh and giggle. And then when you ask her out again, you've built up some currency with her, some emotional currency. And she's being reminded of how funny and cool you are and what it would be like to date you. And we've just followed give, give, give, ask until you either get a date with her or until you basically say, you know what? She's just not not I'm I'm she's not that into it, then the whole idea of abundance is plenty of other options for you to move on to. I'm not saying you do it forever, but you try a couple times. And then it sounds like what you did is after you asked her out, she said, not yet. -- then you just only asked. Right? Yeah. Yeah. Basically. Yeah. Yeah. So, yeah, what you could do is try to reconnect with her and send her a very fun, light text that's only designed to make her smile and ideally respond to you in some way to begin a value offering conversation. And then we get some nice good connection, mutual banter back and forth, then you can say so about that date. Unless you've already married I don't know. I don't know enough about Cosplay. Got the joke off the top of my head. Me neither, to be honest. Unless you're already engaged to AAA Gorgon. Oh, amazing. Would you like to finally get our first drink, or are you spoken for by you know, or are you in a dungeon right now? I don't know.
Tom:
Try it one more time. Because if you don't try, you have a zero chance. Yeah. And if you keep -- Yeah. I do wanna travel all the time. I just don't wanna come from the angle of asking again.
Connell Barrett:
So I just -- Well, that's why we give for that's why you give first. Give first. Give first ask second or, basically, give a give a couple times and then ask for what you want. The mistake most guys make is, oh, hey. Wanna meet up? Wanna date, wanna go out, where are you at? What are you doing? Afre now? Afre now? Exactly. You don't wanna come across that way. That makes sense, man? Mhmm. Alright. Well, listen. Thank you so much for the chat today, the call today. You've done amazing. You've done amazing. You've gone from basically almost a date list or very few prospects from the first time we spoke to four or five dates a week sometimes or at least all these different leads and multiple dates. Yeah. Keep taking action and keep keep showing women that that best hire yourself, Tom
Connell Barrett:
Thank you for listening to the dating transformation podcast. For lots of free tips, videos, and other goodies, Go to dating transformation dot com. See you next time.
Produced by Heart Cast Media.
Welcome to the Dating Transformation podcast. I'm coach Connell Barrett, and I help men build confidence + connect with women by being their own authentic selves.
NYC Dating Coach Connell Barrett
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