Transcript of Make Her Your Girlfriend in Just 3 Dates (Seriously!) Live Coaching with Jack

I like your cake metaphor, by the way. It's easy for me to understand that.

Trademark. Pending.

Got you. Yeah.

Maybe- This podcast is sponsored by Duncan Heinz. Welcome back to the How to Get a Girlfriend podcast. I'm your host, Dating Coach Conal Barrett. I'm the real-life Hitch. If Hitch was a skinny, nerdy ginger who looked like the lead singer from Weezer. Thank you for being with me. I'm here to help you get a great girlfriend and do it by being authentic and flirting with confidence and do it from a place of integrity and heart and not having to use a bunch of sketchy, toxic nonsense of pickup artist moves and being a fake alpha male and all that BS that's out there. I'm glad you're with me. I know you have eight million podcast options, and thank you for spending time with today. This is a coaching episode. You're going to meet Jack, and Jack is struggling with a problem. You might know this problem. Jack is hitting the three-date wall. He's getting to the third date or less. And women are saying, Hey, Jack, you're a great guy. Let's be friends. I'm not feeling it. I'm not feeling those sparks. And Jack did not know why. In this episode, I help him understand why.

I see the matrix. And I think I effectively was able to diagnose the issues that were hidden and give him a roadmap that's going to absolutely take his dating results to the next level so he can get a great girlfriend. You might be thinking, All right, is it really possible to go from hitting the three-date wall to having a woman look at you by the end of the third date and saying, I want this guy to be my boyfriend. Can you really get a woman to become your girlfriend by three dates? The answer is yes, or at least to see you as boyfriend material by three dates. Then even in some instances, actually have a woman say, I only want to date you. I know this because it happened to me a couple of times. Here's a quick story. I want to tell you I got Donna, a woman named Donna, my ex-girlfriend, now ex. I met Donna. Our first date was a couple of quick glasses of wine at a bar. It was very fun, very flirty, very light. The second date was... By the way, I'm giving you what I call the boyfriend experience, the three-date arc for how we get a woman to see you as boyfriend material and the man she wants in her life by the end of date three.

Date number one, keep it light and fun and flirty, just like I did with Donna. Date number two, open up a bit more. Be more vulnerable, more real. Drop a lot of the playful, fun, flirty stuff. Not all of it, but drop a of it and be a lot more genuine and sincere and authentic and vulnerable because that will help her see even more of the real you. For date number three of the boyfriend experience, it's about bringing her into your world. For example, I talk about this in today's episode. With Donna, I said to myself, I want her to be my girlfriend. For our third date, I brought her to my pub Trivia team, Trivia Newton John. I wanted her to see what it was to be with me, not just on a date, but hanging out with my friends, doing pub Trivia, nerding out with other improv people. By the end of that third date, she basically said to me, Hey, just so you know, I don't want to see anybody else. I really like you. She essentially said, I want to be your girlfriend. Within a date or two, it was official.

That is the quick overview of the boyfriend experience, the three-date arc to help you turn that woman you're really into into your friend by three dates or so. Enjoy my conversation with Jack. I hope you love it. Here we go. Hey, Jack. All right, man. Let's get to it. Tell me about your dating life. What are you struggling with? How can I help you, man?

Hey, Conal. I feel I have a hard time with starting a relationship. Basically, when I'm dating a girl early on, it can be pretty easy. I can get a few dates here and there. But when I really start liking a girl, sometimes I feel like I'm pushing her away. I have that issue launching into that actual relationship versus a few dates. I feel like it's easier for me to go further with women that maybe I don't feel that really good, strong connection with yet because it feels easy, less pressure. But when I'm like, Oh, God, I do like this girl, I feel like I'm pushing her away. I guess my first question is, how do I move from that courting stage to a full-blown relationship?

Great question. Help me out a little bit. Tell me a story. If you have a good example from your past with a woman, feel free to change her first name for privacy. But if you want to give a quick anecdote about, oh, yeah, Conal, Jenny and I dated for XYZ dates, and then things went cold. Can you give an example of you struggling with this from the past?

Yeah, for sure. So fairly recently, there's a girl I went on maybe three dates with. I actually saw her a couple of times after She invited me to her birthday party and all that. But I felt like early on, she was really into me. I was like, maybe I was at the beginning, figuring out how do I feel? Because you sometimes have a good first date, Maybe I get my own head sometimes, too. But then you get to your second date and you're like, oh, yeah, okay, that was real. That first date was good. The second date is good. Third date is going well. So with this girl, we went on three dates. And then after the third date, the way I was reading her reaction, I thought everything is going well. In my mind, I'm like, okay, I'm really starting to like this girl. How do I take this further? But then it got a little still where she maybe didn't start texting as much. She was busy all the time. She does have a busy schedule, but when you're busy all the time, then you start realizing, maybe you're blowing me off here and there.

She's washing her hair a lot this week. She must have really clean hair.

Yeah, exactly.

Okay. Has this been a pattern you've seen? Has this happened multiple times with multiple women? Two or three dates in, they just lose that steam with them.

Yeah, this isn't the first time. That's why this is the most recent time. But yeah, it's after a few dates and I'm like, oh, man, I start liking her. But then on the other side of the coin, if there's a girl that I'm like, oh, I'm meh, it's just It seems easier. I feel like then there's something that I'm doing that's pushing her away, that maybe she's reading that, oh, God, this guy is starting to like me. Maybe it's scaring her off. I don't know. I'm making guesses. I just noticed a pattern with my dating.

Let me ask you a couple of diagnostic questions.

Yeah.

Think back to any of these women who, let's call it, for lack of a better term, phrase I've used with other clients, is the three-date friend zone. It's not that she doesn't want see you after that first date. It's just that two or three dates in, a woman basically goes quiet, which is her way of saying, I don't see you as boyfriend, Hatero. That's my interpretation. I assume you're looking for a girlfriend, I assume? Yeah. Yeah, good. You're on the right podcast. It's called How to Get a Girlfriend, so you're in the right place. Okay, so let me ask you a couple of diagnostic questions. On what date do you typically go for and get the first kiss?

So I guess it depends on the date and how I'm reading the girl, but a lot of times it's either the first or second, in my case. Yeah.

Got it. Give me some examples of what you and the What's your most recent woman did, to call her Jane, Jane Doe. What you and Jane did for these three dates, if you recall.

Yeah. So the first day we got sushi, a spot that was close to us and drove It was a separate. Then we made plans. The date was going well, so we went and got a coffee after sushi and got some desserts and just talked all that, and then drove back to her car. Then we made plans to do a second date in the car. And then we were texting and saying, oh, maybe we can meet a day before because she was starting to get busy with her work. We just did a preemptive because she didn't live that far away. We did an improv hang out, go to a coffee shop, got margaritas. We're in a downtown area, just hung out. Then we didn't get to do the third date because she got busy. Then we did another actual third date where I took her to a citer mill, had some drinks. All that.

You're doing some things well already. Okay. So first, we just want to eliminate potential problems that can cause that third date friendzone.

Yeah.

One is that you're not even making any moves. You're not trying to go for a kiss. You're not giving her fun different dates, which you are, which is good. We can cross that off the list. Okay. Yeah, it's good. Sometimes it's good to eliminate things that aren't the issue. And it sounds like another thing, here's a good truism. Women want to feel like things are progressing. Emotionally, sexually, at whatever speed she wants, but some progress. Women want the feeling of progress in terms of two people connecting and seeing who they are And that's also emotional, sexual, romantic, all the different ways you can escalate and lead that dating dance. Can you tell me a little bit about how you feel like... Do you feel like women are feeling that sense of forward progress, or at least that you're to give them that forward progress, or do you feel like you might be getting stuck in some areas?

I think a little bit of both. I think there's definitely some things I can improve on that I'm probably getting stuck at that maybe I don't realize. But I see where you're coming from. I never thought about that way where you're moving forward. But I think I naturally try to do that because you don't want to, I don't know, for a lack of a way to phrase it, I'm not trying to go backwards, right? Okay, good. So in this case, we don't have to get fixated on this one specific girl, but it did seem like we did start off really heavy the first date, and then the second date was casual because it was an improv date. We didn't really plan too much, which was fine. But I thought by the third date, I was trying to show progressing, maybe holding hands while we're listening to the music at this place, this outdoor mill, and there's live music going on. So I guess I don't know where I would need to... I guess I don't know, in this case, what I didn't do.

No, I agree. I'm not hearing that you're... I've had guys say, Oh, Conal, she ditched me after three dates, and I said, Oh, when did you kiss her? He's like, Well, I didn't kiss her yet. Or we went to three straight bar dates, three dates in a row, and basically it felt the same. Women like that sense of variety and full of progress. But I'm not hearing that here. But I feel like you just went, Hmm, about something. What did you say? What were you going to say?

No, I agree. So when you go on three dates with a girl and you feel like you haven't progressed, you haven't even kissed her yet. In In my shoes, I would think maybe she's not interested, and I'd maybe feel like it was in the friend zone. But each time... I did kiss her the first date, this time, second date and third date, but opposite in this situation. Yeah, go for it.

You don't need to play kiss and tell. Although you can, it's an adult podcast. Did it get hotter and heavier as you went along, or was it the same kissing level of intensity all three times?

Got you. No, that's a good question. I don't mind sharing. This time with this particular girl, it was the opposite, where the first time I was a little more conservative and she kissed a lot. She got really into it. We were in the car We were kissing for a while. But then the two times after that, we did kiss and it wasn't as... In my mind, I'm like, Why didn't we do that? But I don't know. So I don't know if maybe she lost interest somewhere down the line. I don't know. I can't read people's minds. Maybe I'm just trying to figure out what I can do. Because again, this is the most recent time, but it's a pattern that I noticed. Okay.

Got you. And what One final diagnostic question here. That's the sexual piece of it. What about emotionally? In terms of two people talking and becoming increasingly vulnerable, increasingly emotional, I don't mean crying and weeping about the day your cat died when you were nine, although, sorry for your loss. Here's the perfect arc of three dates. Okay. Not perfect, but here's a great ideal arc. Date number one, it's really fun, playful, and a lot of flirty, great stimulation, and nice brush strokes of vulnerability, and of course, authenticity, showing her that real you, that real Jack. But at the same time, if we're talking about a cake, it's a lot of Frosting. It tastes really good. And the second date, we give her more cake. Really They start to open up, become more vulnerable, start to give her what I call the boyfriend experience. Boyfriend experience is paint pictures and give women snapshots of what life would be like as your partner because that's what you want with her, potentially. The third date is essentially if the two of you have relatively the same life goals and are relatively each other's type, then by the On the third date, we want the two of you feeling like, Oh, wow, we have a lot in common emotionally.

I get who he is, and he gets who I am, but we also have that nice romantic sexy vibe, and you basically get the Frosting and the cake. Sometimes when a girl goes quiet after three dates, she doesn't get enough Frosting, meaning not enough fun, flirtiness, those emotions she wants to feel, or she doesn't get enough cake. It was fun and flirty and a good time, but she doesn't see the real you, and she can't see a vision of you with her. Through my just made up in my head cake metaphor, what do you feel like these women are tasting on these dates?

Good question, Doug. And I like your cake metaphor, by the way. It's easy for me to understand that.

Trademark, contending.

Got you. Yeah.

Maybe-this podcast is sponsored by Duncan Heinz. No. It should be, though. I'm sorry. Go ahead.

No, you're good. So I guess That's something I haven't thought about it that way, which I'm glad we're having this conversation because I'm putting a whole nother perspective on this now. If I look back in this recent case, I guess maybe I didn't give enough cake, I guess. Maybe I didn't open up because maybe sometimes I get a little bit scared. If I do start liking a girl, like, oh, no, maybe I'm going to scare her off if I get to a certain level. But I I guess I have to come with a realization that if it's really going to scare her off by getting a little, revealing a little bit more about myself, then it probably wouldn't work out in the long run. Okay.

So feel like it was a Too much Frosting, not enough cake?

I guess so, yeah. If I'm thinking back, yeah. Okay. Maybe.

Let me give you some real-world examples from my dating past of what this might look like. Date one, just have a shit a ton of fun. Giggle and laugh and flirt and tease and all the things that I teach and all the things that we can do. I'm not saying it's all Frosting, but we just want it to be a blast for both of you so that we hook each other's emotional. We strum each other's emotional cords. Then for the second date, you want to open up a bit more, and you want to be a bit more vulnerable if you weren't on the first date. It's on that second date where you might start to share a bit about your past. You might tell a story, a vulnerable, authentic story about something meaningful from your past and really open up. I remember on my second date with my then, My future girlfriend, Jessica, I talked about being a fat little boy and getting picked on, having a big ginger red afro and getting teased. I told some stories where I really opened up. That's more like second date, be vulnerable conversation. At the same time on the second date, here's something really practical I want to give you to do.

Start painting pictures for things that you and she can do in the future or that you might do in the future. Talk about weekend getaway. I'm not saying ask her for one. That would be a little too soon. But I'm saying, Oh, man, if you and I could go anywhere for a getaway weekend, where would that be? You can paint a picture of what life with you would be like. Here's a great way to do it. On my second date with my... Let me switch to a different girlfriend. Second date with my then future girlfriend, Donna, I wanted... I did what I call, I gave her the boyfriend experience. No, I'm not a male prostitute. That's not what that is. The boyfriend experience is shifting from Frosting to Cake, shifting from teasing, clarity, stimulation, which feels great, but it's a sugar rush. It's not really nutritional, shifting to something more boyfriend experience. And on my second date with Donna, I said, I want to bring her into my world. It just so happened that the team I was doing pub Trivia with at that point, we were having Pub Trivia night. So I invited her into my social circle, and I wanted her to meet my friends.

And I wanted her to... She literally sat with my Trivia team, Trivia Newton-John, was her name. And I just wanted her to meet my nerdy friends, my improv friends, and my Trivia friends. And I wanted her to see what life would be like with me. That's something you can play around with, is introduce her on a second or potentially a third date to your friends or to a social setting, and really give her a glimpse of what What it might be like to be your girlfriend. Another date idea that you could do to help give that boyfriend experience is for date two or three, instead of another drinks date or another typical first date, do something more boyfriend Do more boyfriend-girlfriend stuff together. Take a yoga class with her or tell her, Hey, I need to go grocery shopping. Do you want to come with me? Then we can make dinner afterwards. That's a boyfriend-girlfriend thing to do. You're giving her a snapshot of what it would be like to be with you. That way, you're also breaking the pattern of what she's used to getting from guys, which is, okay, drinks, and then a put-put, and then a hike.

I'm like, no, do something more... Bringing her into your world is a great way to get a woman to see, Oh, wow, this is what it might be like to be Jack's girlfriend. If she likes it, she'll be in. And if she doesn't or if you're just not each other's type, that's okay. That's not everybody is. But then you're not getting in the friend zone so much as you're finding out she's telling you or maybe you're telling her, oh, wait, we don't really fit as a couple. But at least you're going to know that quickly and you can both move on. Yeah. Thoughts, comments about any of that?

No, that's a good way to put it because I guess it's like, if you have a good first date and you're thinking the second date, you want to just keep... If it was good, you want to keep that going. You want to get that mentality going. Now in my mind, I'm thinking I'm shifting it a little bit because you're right, why waste the time? Why do the Frosting treatment? If it's not going to come to be anything. I see what you're saying. That makes sense to me how you put that. I appreciate the cake analogy, I guess, once again. I'm hungry now. I know. Right. No, you need some substance, and that makes sense. Maybe in the case of this girl, if she wasn't getting cake or any pieces that I was giving her, maybe it was an indication that maybe she wasn't interested. Although, I can't ask this, but it's just frustrating. I wish that I just got the, Hey, I'm not interested. Thank you. But that's just not how it works all the time with people.

You mean You wish that she'd be more direct instead of, What did she do?

It's lingered. I don't know. I've still messaged her here and there, but now she's on vacation seeing family for a month, so she's out of the area. But I don't think there's really anything there because I've tried to reach out a couple of times and I'm not trying to look desperate or needy or anything like that.

My rule about that is with any woman you're into, assert ideal outcome until you and she get it in a win-win way and then everybody's happy, or until you get clear evidence that it will not happen. Defining clear evidence, to me, that would be a straight up, Hey, I'm not looking to date right now, or I'm not interested. Or the polite code for that is, Hey, I'm not looking to date, which is code for, I'm not feeling about you the way I want to feel. I'm not saying that wouldn't sting. I've heard that many times, but at least it's clarity. Or in your case, I would say three good swings at the plate of you trying to see her again. If you go over three, and each time she does not suggest a different time or date, then I would also consider that evidence and move on.

For sure. Yeah, makes sense.

I think you're probably doing that. But some guys give up too soon. I'm not the listener of this podcast, but some guys are like, Oh, don't give up after one unreturned effort. But at the same time, you're not going to try five times because that would be needy. You struggle with dating, right? Sure. You have a good job and cool friends, but you just aren't sure how to flirt. The apps don't work for you, and sometimes women put you in the friend zone. It's frustrating. Hey, I struggled with dating, too. As an introvert and a total nerd, I didn't just live in the friend zone I owned real estate there. But I escaped using the dating philosophy of radical authenticity, which I've used to help thousands of men in 17 countries find love. It's what I wrote about in my best-selling book Dating Sucks, But You Don't, and Radical Authenticity is why psychology today called me the best dating coach in America. Now I want to personally help you attract your dream girlfriend. Go to datingtransformation. Com and book a free call with me. On our call, I'll tell you how my one-on-one coaching will help you find your dream girlfriend, and you'll be doing it by flirting with confidence and authenticity.

No creepy pickup tricks needed. Go to datingtransformation. Com, book a free call today and let my personalized coaching help you get a great girlfriend. To me, persistence plus charm is the secret sauce here of getting an answer. It's like, Oh, hey, Jenny, Janey, whatever. I just thought I'd take one last shot at seeing you again before I head off to Myanmar to become a monk and give up on women. Would you like to go out again? I'd love to see you again. It's please circle yes, no, or restraining order. If you talk to a woman with humor and charm, there's nothing creepy about that. There's nothing needy about that. What's needy Hey, did you get my message? Hey, did you not like me? Do you have an inflatable woman I could date? That would be needy. We don't want that. That's not you, I know. But a high-value, great man, a business consultant a successful traveling businessman in his 30s with his life together, good-looking, cool overall life, you are a massive value proposition. It's never needy and lame to take a shot romance, as long as you're persistent and also you know when to stop, which would be two or three swings and then no answer.

See? Thank you for all the compliments. I didn't even pay you.

I'm trying to give you some frost, man. You know what I'm saying?

I appreciate. Thank you. I guess I have another follow-up question, too. So I guess one thing I've also noticed as well, As you get older, and as you mentioned, so I do travel for work a decent amount, not too much where it's very hard for me to control my personal life. But I sometimes get in a situation where I get busy or she gets busy and then I It seemed like I'm hitting it off with a girl and I'm texting her. I feel like I maybe struggle with that because it's like, Man, I feel like I missed out an opportunity just because her timing wasn't there. So I don't know how to keep a good conversation going when you don't really know her quite yet, any girl. So maybe I call it maybe long distance, quote unquote, but it's just really struggling with that part.

Okay. You're talking about a woman you've maybe had a date with or maybe matched with online, or what's the context we can look with?

I've written this a couple of different times, right? So I guess a scenario would be I haven't met her yet or I went on one date with her, so it's still early. So how do I capture and keep the momentum going when you're not seeing each other? Because I feel like it's hard because now I'm a block of text versus personality.

That's all you are, Jack. You're a block of text. That's all I see you as. I would say, let's look at a couple of different common contexts. So a new match on Hinge or Bumble or whatever profile, whatever app. But you just aren't going to be able to see her right away. Well, you got strike while the iron is hot as much as you have the power to do so. Try to get her out on a date, if possible, within seven days. Much longer than seven days, the iron goes cold. So if that's possible. If it's not possible, then at least get her off of the app as quickly as possible and get some communication going back and forth and try to make a nice strong imprint. In other words, instead of just being a block of text, you could send a 10-second funny little video. Think of it almost like social you.

Okay.

If you have not met her yet, trying to stay on her mind, you could send her little audio messages or quick little videos, as long as you're offering value, But by offering value, I just mean you're seeking to make her smile. You're trying to make her day better, her night better, and coming from a place of, Hey, I want to give a great dating experience to you. And as long as you're doing that, that's not needy. What's needy is being the guy who's trying to take all the time or only asking needy questions. So giving value, funny little videos. I've had many long distance or like, slower burning starts to a relationship or to that first date. The strategies I used are the ones I'm talking about. Funny 10-second video, which I live in New York City. There's funny, weird people on the street all the time. There's like a weird street guy in the subway who dances with this skeleton. I mean, fake skeleton. He does it for tips and stuff, so it's like he's not mentally ill. I mean, he's like a street performer, but it's just a weird visual. So I have a 10-second video I used to send girls.

I'm like, Hey, here's how we should dance on our first date. And then there's a video of this guy dancing with a skeleton. It's just giving her different ways to take you in besides that block of text. So quick little video, quick little audio messages. And a lot of times when you go first because you're the man, your job is to go first and lead the dating dance. Then a woman is like, oh, well, I'll send him videos. I'll send him audios. And you guys start escalating the conversation, and that keeps her interested. Makes sense?

That makes sense. Yeah. It gave me an idea. What's that? So I guess... So I did start... I'm actually traveling because I'm going to a wedding. And I did match with somebody, and I am having this situation. So we are on Snapchat. So if I just sent maybe not the same thing, but we snap here and there, but just a quick video of something funny for a quick little message here and there.

From the wedding?

I mean, yeah, that too.

Weddings? You know, weddings are chic crack. Oh, my God.

What's the best thing to film at a wedding then? What's the best little clip?

Weddings turn everyone, especially women, into human heart-eye emojis.

They're fun.

Yeah. I never used it in dating because I just met my girlfriend. But at my niece's wedding, I have this great video of my niece's grandmother little old lady dancing with me, and she grabs my ass. It's hilarious. And so I think I sent that to my girlfriend early on. But if I was dating, I could have sent that to girls and be like, Oh, my God, check out the old ladies trying to pinch my butt. But I'm not saying try to get an old woman to pinch your butt. But a 10-second video of you tearing up the dance floor, doing the robot, being silly, or everybody applauds as the bride and groom comes in. I don't know. Just a little moment that just says wedding fun will help the woman who you're talking to feel almost like she's with you. You're also giving her a glimpse into your life, which is part of the boyfriend experience of how to get a girlfriend. Yeah, exactly. She wants to see that life. I think maybe back to your first question from this coaching call, maybe just giving women a more vivid glimpse into what a fun, awesome, warm, cool life you have.

That's what they want. They want to be a good, authentic, confident gentleman's plus one in life. Just big picture, philosophically, that's how you want to do it. But back to the wedding, Yeah. Take some fun, get somebody to video you on the dance floor dancing like a total tool. And I mean that in a good way. Or maybe you have great dance moves. I don't.

I have horrible dance moves. That's great. But if it's entertaining, I'm I'm not here for it.

No, women love to dance. I have a client, Benjamin, who started a 22-person conga line at a bar a couple of weeks ago. He was just like, Yeah, it was great. It was like, Great. I'll record it next time. Anyway, back to your question about keeping conversation going. If it's a match, you got to strike while the iron is hot, but get her off the app. Because as soon as you get her off the app, then you've graduated. Try to get her off the app to either phone number or Instagram or Snap or however, whatever is easiest for both of you. Because now you've graduated from her literally dozens or maybe hundreds of likes and matches. Now you're that one guy you're texting with. So that helps.

Fair point.

You were also asking about, oh, what about when you've had one date, but there's going to be a long lag until the second, how to keep that going?

Yeah, absolutely.

Cool. What's your current strategy? How do you do it, if at all?

Oh, God. That's why I'm asking you so many questions. I guess I wondered maybe if there's a...

Knowing what you've already been doing that might be working or what's not working, and I'll say, oh, don't do that.

Fair enough. No, I understand. No, I guess I didn't really have a strategy because I'm like, two things. I mean, sometimes I just live in my own head too much, right? And I'm overthinking and I'm like, oh, am I doing the right thing constantly? Just with every aspect of work, dating, all that stuff. Okay. So I'm constantly worrying, am I being too pushy? Am I texting too much? Am I not doing enough?

That's your definition of being in your head, right?

Yeah. I mean, essentially overthinking.

Yeah. Is this the right thing to text? Is this being too pushy? Is it being too needy? Am I sending in too much, not enough? Is that what your definition of in your head is?

Yeah. I don't want her to scare her away because I'm too interested, but yet I don't want to seem uninterested.

Great. Let's fix this forever right now.

Ready? Perfect.

So simple. Stop asking all those stupid questions. Not that you're stupid, but they're stupid questions. I know because I invented some of them, I think. Perfected asking dumb questions. Stop asking all those questions and instead ask yourself a very simple question. What can I message her that will make her smile? All you have to ask. What can I give her a value that might make her smile? If you come up with something, and it can be as silly as a funny little video from the wedding or a good question that you know she'll like you to ask because it's something she cares about, or a funny dog video, you cannot come off as try-hard or needy or or over the top, as long as it's relatively 50, 50, 60, 40. We want her to help a little bit. But what's needy is... Think about I'll try to boil it down to four words. Here's how to text women. Give, give, give, and then every so often ask. So give, give, give, ask. Give messages that make her smile or might, or that hold interest in something she cares about, or that might make her giggle, or that are flirtatious, or that are cool, fun updates about your life.

Mr. Traveler, you're seeing all these cool sites. Every trip you go on, I want you sending your current best dating lead. Hey, a picture of the prime rib and beautiful Sunday you're eating for dinner. It's like, I bet my meal, I bet my dinner kicks your dinner's butt. That's value because you're giving her a window into your life because you're a high value Okay. As long as you're giving value, you're not needy, and you can't send too many of those messages. We want them to be roughly 50/50 or at least 60/40-ish. But no woman has ever said, Damn a minute, this guy is just sending me too many me funny, awesome, charming messages. What a loser. It's never happened.

That's a great point. No.

Stop being so charming and flirty. God, go away. That does not happen. She might not be your type. I'm not saying she's going to be the one, but basically give. It's needy is asking for only what you want. So yeah, stop worrying about that and start focusing on, hey, what might make her smile?

Makes sense? I got you. Yeah, that I think I definitely fall into and maybe was self-aware that asking questions sometimes just I don't want to be interviewing somebody. When somebody said interviewing a girl that you're trying to date, that's off-footing to me. That was something I always wanted to avoid in the way that you said give, give, give, ask, that flips the script. That's something that actually gives me context of, hey, that's a good thing to I put in your brain and practice it, even with everyday people, honestly, too. I've never been a big texter, but nowadays texting is everything. You have to communicate to everybody that way.

Let's talk about ways to give value by text. Let's get some practical ways. And hopefully I gave some already. I have a 10 second dog video that I've sent to a hundred women. It's two dogs. This is a video I took in my old neighborhood. It's just two dogs in a convertible, little car toy convertible. They're cute. They're two little fluffy dogs, and it looks like they're driving a car dog road trip. It's just an 10-second video I took, organically out in the world in New York City. I've sent that to many, many, many women, and I've said, Oh, my God, watch out for the crazy drivers. These guys almost ran me off the road. That's value because it makes you smile. Anything... Yeah, cute little pet. Do you have pets?

I don't, but I love dogs. Everybody that I know, my friends, brothers, all that, they have dogs. I love them.

Great. Little photos or little videos or photos from your life of you doing something cool and a little bit high status. Think almost like Instagram, vibes of fear of missing out. You know? Like the amazing view of the rooftop bar where you are on one of your work trips. Ten seconds, you could send that to a woman. That's a give. That's a value text because you're not asking her for anything. You're just trying to give her something that might make her interested or smile or maybe feel jealous, but even that's in a way, that's giving. Once you've had a date with a woman, if you know her at least a little bit, then you have more to go on and you can flirt a little bit more. Not that you need to wait till a first date to flirt, but let's say you've had a good first date, you kissed, and you... I'm just making this up. I just made this up right now, but you send her a picture of the sunset at a really cool, I don't know, hotel bar where you're staying on a road trip. You might say, I wish you were here.

Just smile. It can be sincere, it can be genuine, it can be sweet, lovey-dovey, can be a little sincere or very sincere. Basically, anything that might make her smile or make her laugh. It's different from person to person. Or maybe you have in jokes. Yeah, okay. Actually, those are the best value text. Text that you know are personalized for her based on what you know about her. I have a client who... He just had a first date with a woman, and on their first date, they were talking about ChatGPT because he's a huge nerd. They talked a lot about ChatGPT, and she was actually interested in the topic. So I had him write up a flirty ChatGPT search. It was like, Hey, ChatGPT, what's the perfect thing to send a really cute girl who smells fantastic and you want to ask her out for the second date? Can you give me some help? And I I had him take a screenshot and send that to her. I see. Okay. See, so he's flirting with her, calling back on something that they talked about, ChatGPT. Technically, that's an ask, but actually, you're giving in order to ask at the same time.

Let me ask you, what are some ways you might... You can pick a hypothetical woman or a woman you're interested in right now, but what are some ways you could text her that would make her smile or give that value?

I got you. I mean, so getting to know somebody and having some inside joke or I don't know, maybe like... Putting me on the spot. Hold on one sec. No, of course. Sometimes I do a little tease. I'm not trying to... Not like a dig, just like you told me some thing. I'm trying to think of a The recent time. One of the girls I was dating, she went to Ireland for a while and I teased her like, Oh, yeah, totally have an Irish accent. Nice. Or something like that along the lines, something small. But the inside jokes or something that you've talked about that makes a lot of sense. I've used that. It's definitely harder when it's a profile and you've gone on either just one day date or no dates. I do struggle with that a little bit.

Do you have a good strategy for playfully teasing women?

No, I was actually going to ask that for a question. So I guess I guess, because you said something that triggered this question. But I guess I'm having a hard time with flirty text or moving to flirtiness because back of my mind, I'm like, oh, maybe that's going to come across wrong or maybe we're not there yet. So maybe I have a hard time jumping in. And I also don't know what to say that what would come across is romantic or flirty. I do struggle with that part. That's cool.

Good. Let's talk about that. So teasing is a powerful, effective tool that works often, but not with every girl. And it's not like every woman loves it, but some of them do love it. And so it's certainly something to test drive with a given woman just to see how she likes it because that might be her flirting vibe. So it's good to tease, or at least it's good to test the waters. So don't be afraid of testing those waters. She doesn't like it, it won't quote work or it might not resonate, but that's not necessarily going to blow you out with her. It just might not be. That's just not her style, her vibe. Don't fast forward. This is not an ad. It's a free thing that's going to help you flirt with confidence because I'll bet that you struggle with what to say to women and how to flirt, right? Well, let's fix that. I'm going to give you what I call the Flirty 30. These are 30 flirty questions to ask women on the apps or on dates or when you approach so that you can confidently connect with cool, sexy women starting today.

It's time to stop running out of things to say and start asking them flirty questions that are going to make them want to date you. To get your copy of the flirty It's totally free. Just go to datingtransformation. Com/flirty30, and that's F-L-I-R-T-Y-T-R-T. Datingtransformation. Com/flirty30. You're about to start confidently flirting with women, going on dates, and soon getting a great girlfriend. Go get your flirty 30. Let's, again, protect people's anonymity. But can you think of any women you know or recently knew that we could talk a little bit about a date you had or you could have teased her or taken some information about her. Or we can just do a hypothetical girl, or you can use a real woman, but we'll just change her name. How about that?

Yeah, okay. Let's see.

Tell me about a woman, change her name anyway for privacy. But otherwise, you can just keep it legit about her. What's her job? What What's her favorite music? Does she have dogs? What are her hobbies? Basically, the art of flirting is find surface-level things to joke about. Surface-level things. Her favorite band, is, I don't know, she loves Michael Boubouboubouboub You can use something like that. So think surface-level interests and tastes, or think quirky little behaviors that you notice. She's clumsy or she drops. I was on a date once where she dropped this really expensive piece of sushi. It cost me like... I'm like, That cost you $12. How can you know that. I'm going to Venmo you after this date. It's going to get very expensive for you. And the The next day, I'm texting her, Hey, were you able to eat lunch today, or did you just keep dropping the fork? You're teasing surface-level things. You're not teasing hardcore things. Not that you would do this, but you're not making jokes about, well, you sure drink a lot. Are you an alcoholic? You wouldn't do that. Okay, those are some examples. Let's get back to this woman you're imagining.

What are some ways you could tease her or might have teased her, whoever we're talking about?

Got you. I guess I can just use this this recent girl. She's Spanish. I guess sometimes... I was also, before I even met her, I started learning a little Spanish, too. I would make fun of her a little bit with some of the things she said. But also to... I don't want to sound like hard. It's really challenging to learn another language, right? Sure. So I also mentioned, Hey, even though you're bad at that, I'm way worse at speaking Spanish. Just little things like that. I mean, it's stuff.

Here's what you could try with a woman like that. When you're on a date with a woman where English is her second language, you can have a little accent competition. See if she can do an American accent and tease her if it's bad or praise her if it's good. And then be vulnerable. You can say, Let's have a competition. Let's see who does a better accent of the other person.

Okay, I can see that. I went to London. Sounds fun.

Yeah, I went to London years ago, and I remember approaching a lot of women. The thing that my coach had me doing at the time was I would say this to women. I'd say, Hey, okay. By the way, forgive my terrible English accent. But I meet a woman and she did have a British accent, and I'd say, Okay, repeat after me. I would like to buy this cheeseburger with my credit card, and then I would have her say it. It would be terrible, but it'd be really cute because she's trying. I would tease her about the accent. I would try my British accent, which is terrible, and we would laugh about it. You could tease about things like that, tease about pronunciations of words, words.

Yeah.

My ex, my then-girlfriend Alex, more of a girl. It wasn't exclusive. But anyway, my ex Alex, she couldn't pronounce the word rural. She would say rural. I tease her about that. She liked it. Any more thoughts about how you might tease women? Well, here's a simple way to think about this. Do you bust your friends' balls? Guy friends?

Oh, all the time.

What stuff do you tease them about?

I mean, we get brutal. But these are friends that I've known since I was in high school, elementary.

Give me some brutal examples from how you tease your friends. I'm not saying they're right. I just love to hear a couple of examples. Because the whole idea about being authentic and letting women see that real true you is a great way to think about it as well. If I want to tease people, how do I do it already in my life with people I know? There might be some applicable ways that we can do it with women. How do you roast your friends?

One of my good friends. He's pretty short and he's baldening. Just give him a shit for that. And I don't sugarcoat, but he knows I'm joking. Sure. So stuff like that. Okay, I wouldn't go the bald route with a girl.

No. She's not bald. But you know what? The short thing, there's something there. My girlfriend's about 5'2, 5'3. I think I might have said... I totally roast her now. But I know on our first date, I think I said something like, Look at you. You're like fun size. I don't know whether to ask you out or hang you on a Christmas tree as an tournament.

Or pass out for Halloween.

Basically, it's a short joke. But because it's playful and meant with good intention, it's not like a nag. It's like busting balls. Any other ways you tease your friends?

I don't know. I grew up in a very teasing family. I just do annoying things just to get attention, poke the back of the neck. Just people that I know I'm comfortable with. I just like to get under the skin a little bit, and I'm just like, I'm bugging them. But again, I don't know. That's not something I'm going to do to a stranger. I wouldn't say poke her.

I think the easiest thing to do would be to just get present, listen to the conversation that you're having with a woman, and look for little idiosyncrasies. Look for light things that taste. What your favorite movie is legally blonde? I mean, it's okay, but it's not the godfather. It could tease like that.

Or a girl that gets... She says she can't watch scary movies because she's too scared. I roll my eyes and I'm like, They're not that scary. Totally. I want to see how much you jump when you're watching a scary movie. Right. Stuff like that. Okay, so I got some good examples of teasing, but what I guess is another way to be flirty other than teasing?

Oh, sure. Oh, there's a thousand, 10,000 ways to flirt. We just want to choose some simple avenues that are aligned with your authentic you so that you're not doing it. I don't want you to be some cocky teasing jerk type if that's not who you are. That's not who I am, but I am a smart ass. So I want women to see my smart ass side. You might not be a natural smart ass like I am. That's okay. Let me give you a couple of simple ways to flirt. The simplest ways in the world, and they're super powerful. I think the simplest, and tell me if you do this, is just using clear, simple statements of... I call them clear, flirtatious statements of intent, of romantic interest. Basically using your words, calling a woman sexy, letting her know she's sexy, or something she said or did was really sexy or cool, or complimenting her in some other way. You've I've probably heard this tip, so forgive me if I'm repeating something, but I think it bears repeating. Something I want virtually every man to do on every first date, if he means it, is to look a woman in the eye and notice a trait about something sexy about her, the woman inside, and tell her that.

You know what's really sexy about you, Jessica? You are so adventurous. I love that you just got up and went backpacking, went to Europe on two days' notice and went backpacking. That is so adventurous. It's really sexy. I don't meet people like that often. Telling her she's sexy, not just because of her beautiful eyes or her nice figure, which is nice, but she knows that probably. Telling her something about her is sexy? Oh, my God. Women love that. So clear statements of flirtatious interest. You only need one or two per date. You don't need 10.

Right. Okay.

So what clear romantic flirtatious statements do you make on first dates, if any?

I guess, especially a first date, I guess I'm nervous to, so I usually don't.

Well, there you go. This is absolutely contributing. I'm convinced. It's 98 % sure it's contributing to some of these women losing interest.

Okay.

Because that's the Frosting, dude. That's a big layer of Frosting. I see. I know why you don't do it. Well, I have a guess. Yeah, go for it. You don't want to seem creepy. Don't want to seem forward.

Yeah, absolutely. You nailed it. Yeah. Seriously.

You're on a date with a woman you met on a dating app. Why the hell would you not want to tell her be flirty and tell her she's hot, sexy, awesome, if you feel that way?

Yeah, that's a good point.

You're a nice You're a nice guy, right?

Try to be. I would say so for sure.

You and I are both Midwesterners. I know a nice Midwestern when I hear one. Dude, by the way, I'm only messing with you a little bit. I did all these things myself. But you know the nicest thing you can do on a date is make a woman feel sexy and special and amazing. What's nicer than that? So stop being an asshole. Stop being an asshole and not letting her feel sexy and incredible When you phrase it that way, I don't want to be an asshole.

Be nice.

I once dated a woman who she gave me some great... She came out with some of my clients and and myself, years and years ago. I do these in-person coaching seminars in New York City, mainly. And this woman came out, beautiful blonde woman who's basically a part-time model. Anyway, she did a little focus group. Not focus group, a little Q&A for four or five of my guys. Because we spent the night out approaching, talking to women, I'm coaching them up. And then this woman came out. I'll call her Jennifer. So Jennifer, tall, gorgeous blonde woman. She said the best thing. I'm not going to isolate this clip because it would sound so bad. So full context is needed. One of my clients said, so what do women want from us? What do you guys really want? And she said, you know what? We We just want a nice, sweet guy who's going to treat us well and then take us home and respectfully choke us while he fucks us with consent. You know what Jennifer was into, right? Yeah. Again, that's a metaphor. I'm not saying choking is what every woman wants. That's a whole separate episode we'll do about BDSM.

But the message that Jennifer was trying to convey was, We want you to be nice and sweet to us, We also want you to be a man and make some moves. In her case, she wanted consensual choking. God bless her. I'm saying, Lower the bar. Just tell a woman she's sexy and cool on a date. And that's going to help you so much, man, because a lot of women love clear, direct language, unfiltered language, just the way it is. So don't be afraid. Well, fear is okay. Don't let fear stop you from saying that to a woman if you feel that way. You will not get in the friend zone anymore. You may or may not be the right fit for a woman, but I promise you this, if you look a woman in the eye and say, You know what's really sexy about you? The way you laugh and giggle, it is so feminine and playful and sweet and silly. I'm trying to be a gentleman here, but you're making it hard. I don't know if she's going to love that or not, but she ain't going to friendzone you.

Yeah. That makes sense? That makes sense. That's a fair point for sure. Yeah.

So I think what's happening on first dates, at least to an extent, and you're getting first date kiss, so you're doing a lot of stuff really well. But I just really want to hit women, not hit, but give them a lot of great energy and just make them feel all floaty and swirly and special. One of the ways we do that is just clear statements of romantic interest. Again, the technique is notice what you find sexy and special about her. That's more internal, the woman, the person, and wrap that in the bow of you're sexy. I see. Let's go back to your last first date where you felt the woman was cool and sexy. Let's go back. Let's do a back to the future. It's getting the DeLorean. Go back in time. If you go back and tell one of these previous first dates something that you found really sexy about her, what might you have said? What internal quality would you have noticed with any of these women?

Got you. I like a girl that's really bubbly, but I don't know how to say, Hey, that's sexy that you're bubbly, right? But adventurous.

I like bubbly. Yeah? I like it because it's behavior-based. It's not like... We just don't want to make it only about our body.

Yeah, exactly. I see what you're getting at there. I love bubbly. For sure. I tend to like girls that are like that and that personality just is very attractive to me. But I don't know how to complement that and make that sound sexy because you don't always equate bubbly to sexy, I guess. Maybe in my mind, I'm overthinking that aspect. I don't know how to say it that way.

You overthink, Jack?

I know, yeah.

That's all good. Welcome to being alive. Yeah. I'll do it. I have overthought 27 things today. But yeah, bubbly. There's a line in my book where I say, Here's a simple philosophy to go through dating. What I'm thinking and feeling is what I'm saying and doing. I mean, thinking and feeling about her and about us. Right. Right. So, yeah, if you're like, You know what's really sexy about you? You're so bubbly. I love that. It doesn't have to be fancy. It just has to be real and And that direct, clear, you statement, Y-O-U, You know what's so sexy about you? You were so bubbly. I love how bubbly you are. And then you might keep going. Just let that stream of consciousness flow. Was she intelligent? Was she... Anything else besides bubbly that impressed you?

Oh, yeah, absolutely. The fact that she loves to travel. I mean, not everybody likes to do it. And adventurous. Awesome. Smart, having a really good job as an engineer. Okay, great. Yeah.

Oh, that's awesome. You just did something, you stumbled on something. This is more of an advanced flirting move for a different episode, perhaps. But when you combine two things that don't normally go together, you create this interesting curiosity. It's like Reese's Cup of flirting. So chocolate is good, peanut butter is great. Put them together? Oh, my God. It's incredible. So you're like, You know what's really sexy about you? What fake name can we give her? What's a bubbly girl's name?

Veronica.

I like using a woman's name because that's her favorite word. Hey, Veronica. By the way, Veronica, you know what's really sexy about you? You are so bubbly. You're not just bubbly, but you're so smart and nerdy. I mean, you're an engineer. You're a bubbly and brilliant engineer. I don't know whether to ask you out again or ask you to design a computer model for me, or I don't know, whatever an engineer does. But it's like you're combining two things that don't normally go together. And that's really unusual in a good way. It gives women a sense of variety that they're not used to because most guys are just like, You're hot. Actually, most guys don't even say that, but at least the quote, unquote natural guys or more naturally extroverted guys might just say, Yeah, you're hot. That's not fancy, but it's enough for a lot of women. I'd much rather you elevate it to be like, Hey, you know what's sexy about you? You're bubbly But you're also a nerd. I love that you're a bubbly nerd. You're so my type because I'm a nerd, too. I'm not as bubbly as you, but that's okay.

That would resonate so much with a woman, I'm convinced. I really do believe that.

Yeah, that makes sense because when you're complimenting, it's not generic. It's really... I'll call them back to what you were saying earlier. It's two things that are unique about her that you can't really say about everybody else. So I get that because I would like it if somebody said that about me. Not that specific because I'm not an engineer. I don't know if I'm bubbly. Maybe I come across the opposite sometimes, but yeah, absolutely.

Well, women are usually the bubbly one. I'm not saying bubbly is a thing a lot of women are looking for in a guy. That's probably good. Yeah.

No, I guess. I agree with it.

There are some feminine traits women like, I'm not saying bubbly is going to be at the top of the list. Okay, here are your marching orders. Here's your mission or two, should you choose to accept it. On every first date going forward, I want you to give women that sexy compliment. Make it about an or a behavioral observation. Her sexy laugh, her bubbliness, her intelligence combined with bubbliness. On my first date with my now girlfriend, Jess, I said, You know what's really sexy about you? You're so quick-witted. You're so funny. I'm usually the funniest one on a date. I'm just trying to keep up with you. And she later told me how that melted her.

That's a good line.

Well, it's a line, but it's also genuine.

It was real. Yeah. No.

I mean, it was a thing I said. It wasn't planned, though. Totally. Totally organic in the moment. Authentic, as I like to say. Anyway, marching orders, always say the sexy thing. But wait until you mean it and feel it. Don't say it because Coach Connell said, Oh, time to do the sexy part. Time to do the sexy line now. Hey, Jennifer. My overthinking.

You sure are sexy. I'm writing it down on my arm.

It's another thing I wanted you wanted to do. Be vulnerable. If you are in your head and nervous, tell her that.

Okay.

Because you get in your head. So she. Be vulnerable. God, I'm just nervous right now. I'm actually in your head. I just caught myself trying to say the right thing. And you know what? I'm not going to do that with you. I'm just going to be in the present moment with you. Back to you. What were you saying, Allison? I'm back in the present moment. Sorry. Pretty girls make me nervous. Oh, my God. Women are craving that guy. That's like a Hugh Grant rom-com movie character. Trust me on this. Okay. Anyway, so sexy compliments. Feel free to say when you're nervous or in your head. I'd rather you lean into the skid than pretend like you're not human. You never know. She might open up, too. All of a sudden, she's like, I was so nervous, too. You're so cute. I was so excited about you. The other thing I want you to start doing for a mission is simplifying texting. Start using give, give, give, ask Ask. And just instead of thinking, What's the perfect thing to say? Or am I coming off as needy? As long as you are giving value or trying to, then there's nothing needy about you and nothing try hard.

And you can't... Again, no woman's ever said, Stop sending me charming, funny messages that are tailored for me. They want that. So don't worry about that at all. I've been doing for 20 years. It works like a charm.

Makes sense.

Okay.

Any other missions? These are good.

Thanks, man. Last thing I'll say, I got two more minutes. Do you tell stories on first dates? Like personal stories from your life?

Yeah, absolutely.

Yeah? What's your go-to story? Any stories you like, you don't need to tell the whole thing, but close-knops version?

So, yeah, I try to lean towards I have a younger college or kid's story that I try to think are funny. I'll say one of my brother, when I was really little and I pretended I fell off of our deck and I was looking up in the air and my brother, I just see him. He's this tiny little kid that has this giant ice chunk that just drops it right on my head. I'm just crying. Something like that. That's great.

I love it. That's great. No notes. As my improm teacher never says to No notes. That's great. Storytelling, personal stories are great things to share. One thing you might consider, back to that Frosting versus Cake topic. This could be first or second date. Totally fine to do this on a first date. Is think of a good vulnerable, or you don't have to think of it, you can also just do it in the moment. But think, what's a really genuine, real story from my past about something that I screwed up or something embarrassing or something really personal that I've learned from or grown from? That can be really powerful. Like, late in a first date, after you flirted and teased and told her she's sexy, and then open up a little bit toward the end, and then she sees that real glimpse of you. I remember on the first date I had, way, way, this is pre-pandemic, it's been so long, but pre-pandemic first date I had, where I talked about giving my mom's eulogy. Because we were talking about the best things we'd ever written, and the best thing I ever wrote is my mom's eulogy.

And I wasn't going to typically talk about my mom's passing on a date, but it came up. And I talked about it in a way that wasn't sad or super negative. It was more about what a wonderful moment that was for me to share these stories about my mom with my family. And so broke a little first date rule. Talk about your mom's eulogy? Hell, no. I wouldn't normally I tell that to a guy, but it was organic. I could just see this woman just gravitating to the truth and the openness, and she shared something about her past and somebody she lost. It just made us really see the real people. That will help a woman at the end of a date walk home thinking or go home thinking, damn, I could totally see myself with this guy. If she can't because you're just two different people, that's okay, too. Better to find out sooner rather than later. But, man, when you find the right fit for you and you get emotionally naked like that at the end of a date or maybe on a second date, that's another story to have in your back pocket is something vulnerable, lesson you learned, something you screwed up, the time you got caught cheating on the sophomore high school test and you got suspended, whatever the story is.

Make it a story that doesn't make you look good or that at the time didn't make you look good, but you learned from it. That can be pretty powerful, too.

Okay.

Oh, bonus mission I forgot to give you. Also, look for one thing to playfully tease a woman about on first dates. So marching orders for first dates, sexy compliment, and mean it, don't fake it. Look for something to tease, something behavioral or low stakes, just like you bust your friend's balls. And then look for that more vulnerable story and start giving women the boyfriend experience because Jack is going to be a hell of a boyfriend. We just got to show women that guy.

Thank you. Cool, man. Thanks for the confidence. You got it.

That's all. I will let you go, and we'll stay in touch. Keep me posted. Okay, bro.

Awesome.

Thanks, Kyle. I appreciate it. Great stuff. You got it, man. Thanks a lot.