#520 What He’s Really Thinking in the First 3 Dates: Flirting, Communication & Navigating the Early Days of Dating with Dating Strategist Ben Hart
4 Nov 2025 · 54 min
Heather Monahan talks with dating strategist Ben Hart about what men think during the first three dates. They cover flirting, communication, and how to navigate early dating without overthinking every move.
Chapters
I think that dating specifically for a lot of people is difficult because they've developed a structure around a lot of other aspects of their life, like their work and their school and their gym routines. Like, there's a lot of structure associated with like, you do X, you get why. And I think that with dating there's not a lot of structure. A lot of people have this really unique Disney story fairy tale attached to how it should happen. And not a lot of people actually like to think about dating so strategically. And I get it, I get why it's not an attractive thing to be like, oh, what do you mean? I got to do this, this and this. I'm like, well, you don't have, no, you don't have to do anything. But, but if you think about it a little bit more strategically without focusing on the hard truths of the details, just strategically framework and then like think about how to progress that aspect your life. Like, you know, if you don't think about dating or dating fundamentally with more purpose or more intention, then I don't, I don't see how you just expect things to happen.
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I'm ready for my close up.
Hi and welcome back. I'm so excited you're here with me this week. Okay, so let's get to the guest right away. Ben Hart is a globally recognized dating strategist. Ooh, that's interesting. Author and content creator with a worldwide following of over 700,000. Known for his no nonsense, humorous, which I like and heartfelt approach to dating, Ben helps people take charge of their love lives by leading with authenticity, embracing setbacks and showing up as their best selves. He is the founder of Dating with Purpose, a coaching program and community that empowers daters to stop sitting on the sidelines and start creating meaningful connections. Who doesn't want that? A New York based entrepreneur and public speaker, Ben is also the author of the Zero A Transformative Guide to Creativity and Reinvention. With a background in psychology and biology and advanced training and personal development, Ben has spoken on stages from the United nations to Ivy League universities, sharing tools to help people reset, rebuild, and realize what, what they truly want in life and relationships. Ben, thank you for being here today.
Thank you, Heather. That was. You're just, you know, the way that you hype it up. You're just such a stage person. I love it.
I'm a hype I'm like everybody's number one hype guy, right? Like, I totally am. Okay, now, Ben, let's get to this. I told you offline, one of my girlfriends, Vanessa, who got me to bring Nico on the show, she got me to bring you on the show. She is a huge fan of yours.
So.
So take me back to. And I've been down the rabbit hole. I love your content. I love what you're doing and love the humor that you add into dating relationships. It makes it fun, which I think is so important. Tell us a little bit about, like, how does become a dating strategist by, like, where does all this happen? Like, how does it happen?
Yeah, it's a good question, by the way. Shout out to Vanessa. Shout out to Vanessa. Gave her a little shout. Where did it come from? You know, honestly, I came from the entrepreneurship space. I had a startup in my 20s and we merged with a media company and. And then I started doing some consulting and I was doing some content around high level personal development, which is kind of like where my book. I wrote a book called the Zero mindset back in 2021. And you know, kind of like it was around recalibrating points of zeros in your life so you can develop a different mindset, you know, risk assessment, ideas of failure, what that meant, redefining it. And it kind of like niched itself into the dating world. Like, I've. I've been. I'm fascinated with the details and the intricacies of interaction, specifically in the context of attraction and dating. So I find that. I've always found that super fascinating to me. I've been like, you know, and I have my own personal history of dating in New York for over 20 years. Like, I kind of understand some of the things, you know, and that's, that's what kind of makes it maybe more unique than some others is that I try to make it fun. And I started doing dating specific content in 20. What was it? 2023. End of 2023. So I kind of took the content I was doing, which was very general high level personal development. You know, it was just a little too gray, if I'm from being honest. And I, I understood that too. But when I started to say, you know, I said, fuck it, let me just talk about the shit I really want to talk about. And I use TikTok as a playground for that. And then the first video I did, it just kind of started to go. And then I realized that obviously the, you know, the dating niche is a very interesting One, but I realized that I was going to quadruple down on something that I feel like if you just ask me a question, I could just kind of go on where some other topics I was like, all right, let me think about 1, 2, 3. These are kind of things I can kind of just flow with. It became more of like a flow state thing for me, and that's kind of just how it really started. And then, you know, everything for me over the last year and some change has been a result of me using TikTok as a playground.
That's so interesting to me. And I love that you had the confidence or courage to create pivot from what you were doing, to try to lean into something new and then see that this was actually coming easier to you and that allowed you to make that transition.
Yeah, it was like a point of zero for me. I didn't know what to expect here. Right. Like, it was. That's. That's one of the reasons why TikTok was big for me, because it was a place where nobody knew me. And that was really important because I didn't have an identity box. I've already established, like, you know, when you're on Instagram or, you know, you're all of a sudden you're a long lost ants there. And then, like, other people are starting to be like, who, who's this dude now? You know? And TikTok was that thing for me. It was like, nobody knows me. Let me just say the shit I want to say and test it out there. And then when I did that, you know, after like nine, ten months, then I brought it to Instagram.
So it took you a little bit of time to get more confidence in what you were doing so that you felt you weren't an imposter.
Yeah, I felt like it gave me more. It took a while for me to gain the confidence to give it, to distribute it and talk about that around people I already knew. You know, like, that's kind of the identity box. You establish an identity and it becomes a perceived risk when you're like, well, do I want to hop out of this box and do I care? Why do I care? Which everybody cares to a degree. And then, you know, there was a point that it came where I. Where once I started to get more wildly accepted, I started to care a little bit less.
So it's a journey to get to the point where you can actually take a leap.
I think so, at least for me, it was. I think it is. You know, I think depending how deep engulfed you are in, like, in an identity. I think it could be more risky for people.
Yeah. I can just give the analogy for everyone listening. When I left corporate America, I wanted to go to work for myself, but I was so scared, to your point. And I didn't want to hear from the naysayers. No, go back to corporate. This is what you're good at. I wanted to tune that noise out. So I quietly was writing a book and not telling anyone. I was doing all these things like you were doing it on TikTok to build up your confidence. I was doing things silently and not letting people know. And even once I finally had it out, I still was. I wasn't changing my profile on LinkedIn. I was still. There's trepidation, and for me, it was really around imposter syndrome. But once you. You get to a place, you're like, wait a minute, I'm getting a little traction. I gotta rip the band aid off. And then you go all in.
Yeah, for sure. And that takes some time sometimes for people. Right. Like, different people have different. The way they absorb that kind of pressure or perceived pressure from society or their. Or their close circles.
Okay, so your ideal client, the people that you work with, are women.
Yeah. Yeah.
And what is the age group that you're targeting?
Quite honestly, I think it depends. Right. But most of the women that do tend to follow me and the advice I tend to give, I would say from, you know, it kind of goes. Right. I have given you an example. I have a one in my group that's 78. It does span a little bit, depending on where you're at. Right. And most people that are starting to want to date more intentionally or with purposes like to call it, are people that have kind of gotten past the fun moments and want to take things a little bit more serious now, and that tends to be more around like 28 to 55. If I were to give like an average.
Okay. So you've worked with a lot of women at this point. You've got a lot of feedback in regards to what's landing with people, what's not, what are you seeing generally for people listening, like, what are some of the biggest issues that you see that you're like, right away, you know, oh, we're going to have to deal with this with women dating.
Yeah. I think the women dating thing has been very interesting for me because that's. That became a very quick focus point of mine because I realized that their troubles are very different from a lot of the male troubles, especially in that age bracket that they want to start taking things a little more seriously and when they, you know, there's a struggle. So I always kind of say this reference for men, it's most of the time it's about their struggle is getting to date one. And for women, their struggle is typically past date one or three. And they're trying because they've already kind of chosen a guy that has, you know, they've, let's say they've cut 45 out of the 50 that have come at them approach them, but the five that they've chosen, they start to get a little more invested in when they start to go out with them. So two specific struggles. Number one is navigating after date one, which is like how to maintain, how to not get so attached to an outcome, how to stop telling stories about what's going on and what's not going on. Whereas I think guys have a little bit less of that as a problem. And number two, what I see being a bigger issue is sometimes a lot of women can get in their own way in terms of being approachable or open for the kind of guy they want. So those are the two. The two things is like being approachable and open to the kind of guy you want. Kind of like low key choosing. And then the other part is kind of like keeping and maintaining early stage up and not driving yourself crazy.
Okay, so give us the feedback that you have on both of those points.
Feedback in terms of like, what do people think of them?
What advice do you give to women that are telling themselves stories that aren't true, that are getting too attached too quickly, like how do you respond to them, these two big issues that you're seeing?
Well, there's, number one, I think that they get very confused because they're trying to figure out how does the guy feel, what does this mean when he does this? What happens when I don't talk to him for a week? The reality is there's two things. Two things that, that qualify. A guy showing interest that that means he's interested. Number one, does he take you out? And if he doesn't take you out, it's really irrelevant at that point. And, and number two, is there some realm of does it get to a place where he's showing committed behaviors and it leads to some kind of commitment? Because most women I talk to are always looking for some sort of commitment. They don't want to just be out here and dilly dallying and have a good time because then at some point they actually do Get a little bit more attached to this guy. And they actually don't want to date four or five others. They're looking for one dude that they really like. That's one. Number two is one of the things I always emphasize is, you know, I talk about past proximity, eye contact, smile. Those are the three kind of like buckets that I put in for like sending choosing signals. Stop being so face down. Because a lot of guys are not going to approach women who are not approachable. Now, sure, there's a select few of women that are going to get approached no matter what they do, but that's not a majority of women. And people have to understand that maybe you don't live in that category. Maybe you have to actually be a little more approachable, friendly, make some eye contact, crack a smile here and there, get around him. That's why I call it pets. Proximity, eye contact, smile. So those are the kind of things I typically tend to, the intricacies and the nuances of being approachable and then like the framework of how to maintain the interest post date 1. And sometimes, yes, I advise getting a little flirty, but I also understand that, like, don't get so attached to a specific outcome, like trying to close a deal. Like, we're not closing a deal here. You gotta. You're vetting him too. And sometimes people forget that. They forget that once they choose. They think that I kind of like this guy. But you're vetting him too. Along the way, you should be seeing his behaviors as they unfold, as he's doing for you.
Oh, I love that.
Yeah.
Because I think so often, especially if you're dealing with women who have some success in business, they're looking at more like what you're saying as like, okay, this outcome that I want, this relationship that I want, and where are we versus that outcome. Instead of, wait a minute, do I want to keep showing up and choosing this person after date one, day two, and day three?
Yeah. And I think that's an important question to ask. And, you know, it's also an important question to ask is when you consider, like, okay, I want X, I want X type of guy. What does X type of guy want? And I'm gonna tell you, not a lot of women ask that question. That I could definitely tell you. They don't ask the question of the kind of guy I want. What is he looking for? And I think it's. Listen, I. I think that a lot of women that I speak to a lot, they're on my channel. It's Difficult because when you're in a place where you've never really had to like understand men, you know, because a lot of men kind of have to understand the basics of women just to get. Get to first date, which is like, well, what's going to turn on? Why did I just turn her off? Like, why did she turn me down there? Like, what was the deal? There's a part of them that have to be that. And when you've never really had to understand man when you, when you choose the guy, all of a sudden you start to have to understand the behaviors a little bit more and make, make some good decisions. And sometimes that can be difficult for people. So I try to make it fun. But my method is essentially it's. It's all about, you know, I'm much. I'm very big on accountability. So I do put the mirror up to a lot of people and I don't. I'm not a big back rubber. And not to say that I couldn't be, but on my one on ones I definitely am. I'm understanding and empathetic. But in general, you kind of have to look in the mirror if you keep attracting f boy. I mean, there's a common denominator here and you can't just be thinking about it's everybody else's problem. And I think that's very empowering. And I think that that can kind of get the message, can get a little diluted if you're not considering it actually an empowering thing, that you actually have more control than you think.
That's so true. You remind me of a conversation I had earlier with one of my girlfriends who's married. And I feel like this advice, it doesn't stop with dating, right? It's still in any relationship. But you need to more look at yourself and how you're showing up daily to get the responses that you are getting and what can you do to change if you want a different outcome, if you want a stronger relationship that goes for wherever you are in life. Totally.
And like, you know, I don't. My point is I also don't want to see people get caught up in this like victimhood of like, you know, for example, there's plenty of them. But like, I give you one. Like, you know, there's okay, a guy was. I was in a situationship with a guy for six months. I don't know what to do. I'm like, why would you be in a situation for six months? You know, like that, right? There is a basic level of like, Framework of accountability. Like you don't do six months situationships with a dude when you're looking for commitment as a whole doesn't work. Like the fact that you actually had control. Whether this goes to a situationship or not, it's not just on the man. Because he led you down a situationship, you kind of stayed.
Okay.
What is a situationship?
A situationship is basically anything besides relationship. And if we're getting very general about that, that's a very general framework, right? Like it's anything besides relationship. You know, you, you hang out a lot, no commitment, you do friendly stuff together. It's, you know, maybe you sleep together or whatever, but there's all these other things where there's no commitment. And that's what most people would call it's a situation ship, kind of.
So not having a conversation or communication that we're in a committed relationship, we're together, we're not dating anybody else.
Correct. Not having that conversation. See, like if, if you're somebody that cares about it, right? Like if you're somebody who says, yeah, you know, for example, let's say most women that call in, yes, I am looking for, you know, I would like a commitment that leads to marriage one day and I would like to have a family. Let's just give a classic example, okay? There's an identity that happens, right? You have. This is the way I like to think about it, the way I always talk about it and teach it is there's outcome and then there's who do I need to become to get outcome. And just like anything else, right, like if you want to get into Harvard, you got to become Harvard student first before you get in the Harvard. You can't say I'm, once I get into Harvard, then I'll change. No, you have to say, okay, if I want to be that. How would somebody like that carry herself? How would she make decisions? What would she put up with, what would she not put up with? And going to tell you a lot of people that are in that framework of commitment or one would call maybe wife or a husband wouldn't put up with certain, certain behaviors that are not conducive for long term success inside relationship. And that means no long term situationships. You don't need to do all this stuff. And they would communicate thoroughly, they wouldn't be doing all this, that I, excuse my language, that I always see happen and then blame the guy because he was a narcissistic, manipulative dude.
Well, give us an example so that everyone listening can Relate an example of.
Like what I hear. Yeah, well, I was seeing this guy for, you know, this guy is nine years older than me. I was seeing this guy for six and a half months and now he's telling me that he doesn't know if he wants to commit. He's still feeling things out and I don't know what to do here at this point. How do I get him to commit? I said, well, you can't get him to commit, number one. But number two, you stay in a situationship way too long. You shouldn't have been in situationship. You should have required commitment in order to continue this thing at month two and a half max. Three, if that's what you wanted. And especially now, it might be a little bit different, right? And I say that I'm giving a specific example right now. But if somebody, if a young girl says, hey, you know, I would like to have a family and I'd like to get married, then that is pretty much a line you should start to draw now if it's not that big of a deal. If you already have kids and he already has kids and. And you guys just want to find somebody to share your life with. The rules can kind of bend and twist a little bit, but at the same time, you should still be transparent and communicative about those things that are important to you. So that's kind of one situation I can kind of outline.
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I asked you to try to find your passion. Let me I like to give specific examples. No names are going to be used here. We don't want to enter any of my friends but so I have a very good girlfriend actually a few good girlfriends who happen to be in their 30s. So to your point they don't have kids yet. They haven't been married. Right. And I agree I'm 50 with a child. It's totally different dating at different times in your life because you don't have the same pressure. Right. And I completely for anyone listening right now in your 30s that wants to have a baby, I feel you and like do it. So to that end and it is a weird thing that it happened to me when I was I turned 30 all of a sudden I woke up one day and I wanted to have a baby like it lit. It happens that fast. And for men listening to understand a woman's not crazy all of a sudden you just have this strong calling to do something. It's going to change the way you behave and the decisions that you make as a result. Now a few of my girlfriends in their 30s are really directive and draw super hard line. They're beautiful, they're great people. But I watch them and I take A step back, Ben, and I look at them, I'm like, you're crazy. Legit crazy. This is how I see it. I see them as being nuts. How can you expect a man to know in 30 days, 60 days if he wants to marry you and have a baby? Like, it just seems like a lot of pressure and drawing these hard. So what is your advice or direction for women in their 30s that do want to have a baby, but to my point, also don't want to be a lunatic and think people can just decide in 30 days if they're going to marry you or not?
I completely agree. By the way, as far as the marriage thing goes, that's like a different category. I think you got to get to know people a little bit. And, you know, I, I personally, especially for somebody in the 30s, I give it around like a year before he figures out if he wants to marry her, but. Or vice versa. But at the same time, right on the flip side of it is, like, when I say hard line, the sand, I mean, there's. It's a hard line is kind of the way you communicate that hard line. Some people are like, oh, I'm not. I don't do this past that. And then that's probably not going to make somebody very interested to keep continuing with you anyway. But if you voice your. If you communicate thoroughly about what it is you're looking for, like, hey, I've been having a really good time with you. I really enjoy this. But at this moment, I am looking for commitment to go things forward. That's really important to me. If that's not where you're at, I totally get that. But that's just kind of what I'm going to need to move forward. If that's not it, I totally get it. That's a different perspective to have after, you know, 10, 12 weeks. And he's not saying he's going to marry you. He's saying, yes, I want to commit to you. Because commitment is. Is on a route to make maybe something a little bit deeper than that. And so I think that's very important. I think it's important to have intentions and purpose, but understand that, like, there's a way to communicate those things that make somebody respect it and say, yeah, that makes sense. Like, some guys don't really see commitment in the way that a lot of girls do. Some guys, if they hang out with you long enough, they'll just be like, yeah, we're in a relationship. We just never talked about it. But, like, why do we need to talk about it. Whereas a lot of girls are like, no, we kind of need to communicate about it. Because I want to know, I want to feel secure, that when I'm with you, you're not seeing anybody else. I'm not seeing anybody else, and the investment makes sense to me. So there's partially that. And I think that if you communicate some of that a little more thoroughly and have some expectations so he understands where you're coming from, and if he doesn't want to, then cool, he doesn't want to. But marriage, I think is a little bit more longer. But even just the first level of commitment, if a guy doesn't know he wants to commit to you after three months, I mean, that's kind of a problem, especially in your 30s.
So what's the right way then for them to approach it? Because to your point, hardlining someone really aggressively, in my opinion is not. It's going to backfire. No one wants some woman attacking him, asking to be in a relationship. However, you need to communicate your truth. You need to communicate how you feel, what's important to you, and what you want. What's the right approach that you think women should take?
I think the one I just kind of mentioned is, seems to work very well with people because it's letting them know that you don't want to last in a situationship because you're looking for other things in your life. And if that's what he's looking for, no problem. That's like a, that's like a soft line that you're trying to draw because you, you should have boundary here. Like you don't want to continue in these long situationships and then waste. All of a sudden you get in one, two, three situationships and all of a sudden you got like three or four years out of a prime moment for you. I don't think that's fair enough. Right. And I think that you need to communicate it in a way that's understanding. After you vetted a little bit, a lot of women that I speak to are trying to figure out commitment a little too soon. Like couple weeks in, they're like, well, I don't know, you think he's going to commit? I'm like, well, you're still vetting him, you're still going to get to know him. And that's why I kind of give the framework of like the two and a half, three month mark, because it's fair enough. You guys have one, maybe two dates a week at that point, you know, that's a good like 12 etc dates in there at minimum. And if he doesn't know if he wants to commit to you by then, you kind of have to make a call on it. And you can't just say he should have done it. Well, he's not control your life and he might see things very differently. So you should take control of your life and kind of do something about it. It doesn't have to be a hard line, but it has to be like, oh, hey, if this is not going to continue, I totally get it. That's fair, that's respectable. And he can only say why I really respect that even if he didn't want to.
What do you see in regards to men and women with masculine and feminine energy in dating today?
What do I see? It depends, right. I think this like idea of femininity and masculinity has gotten a little overplayed. But you can kind of see them go both sides. I could see you see more productive, successful women in the workplace that have kind of developed what one would call or consider a little bit more of masculine traits. And maybe you've seen that as a result as a response, a lot of guys have sat back a little bit more and not been overly aggressive in their pursuit in some sense because of a variety of reasons which we can get into. But I've seen a little bit of that. Right, You've seen a little bit more of a lighter pull on men just because of like their jobs per se and what they do and maybe the testosterone is going down, all these things are playing a role and you know, hypergamy is. Tends to be typically more real than not. And there is that and that, that, that affects how women and men choose for sure.
So when you see, because I see a lot of this and I know this has been a situation for me, when you see women that have achieved success in corporate America and are very directive and more masculine in their approach and that starts bleeding into their relationships. I'm sure you've seen this with some of your clients. How do you direct them to manage that or balance it?
That's a really hard balance. I'm not going to lie about that. Right. Because guys don't have that same problem. So I have to acknowledge that first women tend to have that problem because they think of this like a switch. I don't think of it as like a switch. I think of it as like, you can, by the way, some of the most productive, successful women I know are highly actually more in their feminine because in my opinion I feel like the feminine controls the chessboard. And they, some people haven't really figured out how to use. And they use it as like a competitive streak to like, compete with men. And then they want to like, shut off the switch. And that's difficult. I think setting off that switch is hard to do, and I don't think that's easy. And I think about it very differently. I think about, you can be this way and you don't have to see. A lot of girls will come in and say, well, he didn't make me feel like I could be feminine enough. And I said, well, why is it so conditional? Why is your femininity so conditional? If a guy said this to you, you'd laugh him out the room. Well, she didn't make me feel good enough to make me be my masculine. You'd be like, come on. And I understand that there's traits of masculinity that, that go into your, your job and everything else. But you have to understand also too, a lot of times when you have that framework, when you're meeting new guys, some guys look right past you because of that, because of how hard you are on the outside. And more like that, some guys, the guys that most of the women actually looking at are going to look past them just because it doesn't. It's not, not the most attractive thing on a superficial. And now if they get to know them, fair enough. But you can't assume that somebody has to break those walls down so quick right off the bat.
So how do you work with women to help them be more in their feminine where you're the most powerful place for them to be.
Yeah, and I'm not gonna lie. Like, I'm not a femininity coach. So I don't like, teach them all these details about how to be more feminine. I think that would be a little bit out of my league if I'm being honest. So I kind of, I feel like I kind of know my limits. Like, even people call into my stream. Like I have a live stream that I do on Tick Tock Monday through Thursday. And they'll start going into like, childhood stuff. I'm like, listen, I'm not a therapist. I'm not gonna lie to you. I'm gonna stop this right here because one, I'm not qualified. Two, I don't talk about relationships, and three, I don't talk about marriage. I specifically stick to early stage dating. And I think that's important because the early stage is like, how do you start to attract the Kind of guy you want. And I think a lot of the qualities I was talking about being just a little bit more, I guess we use these buzzwords like feminine or a little bit more softer, a little more open, a little more caring, a little more present. You're presenting in, in that light as opposed to presenting like you're, you're a ball buster. And I think that when guys sense the ball busting, they tend to leave.
So maybe let me reframe the question. You talk about how a woman can flirt in different ways. They can flirt. What are some of the ways in that regard?
Oh, for sure. I mean, I talk about a lot of different things, right? So a couple things I kind of made up along the way. Which is the pest, which I originally talked about before, like the basics, fundamentals of flirting. And I talk about the double bag Bonnie, which is like eye contact and looking back when you pass a dude, you know, you make eye contact, you pass them, you look back. It's like giving the keys to the Kia. I talk about a lot of different ways to flirt, but like I always talk about breaking the touch barrier. Like these, you know, eye contact, smile and breaking the touch barrier. Specifically like on date 1 or after date or after date 1 are little things that you, that you will start to see how fast they start to ignite men to want to do more for you. And I feel like when you don't have those tools, it's harder to get men to be like, oh yeah, I really want to step up. Because, you know, honestly, yeah, a lot of men are a little bit driven by ego, but they're driven also a little bit by like they want to be able to do something here. And if they don't feel like they can do, there's very little they, there's little ambition to want to do. So I think that's important. That's why I kind of like, I always talk about like, you know, when you're walking next to him, grab hook his arm, like little things like that, they're going to make a huge difference in how he treats you moving forward. So I talk about those things which I feel like you could say that could play a little bit in the being a little more feminine, but it's really just being more open and flirty.
But, you know, it's interesting. And my girlfriend Vanessa was telling, telling me this. She's talking a lot about the looking back idea that you have. And one of the things that came to my mind was this. If someone is not super confident in themselves I would think of myself if I was single and at a bar and someone locked eyes with me to look back at them. That takes a lot of courage and confidence, don't you think?
I don't know. I mean, listen, I could see. I could see a woman's perspective on that. But, like, where's the L? Like, where's the L? Like, what's the fear of, like, what's the fear associated with. I'm just trying to understand. I get these questions all the time. I talk about all the time. But, like, where's the. What's the L you're fearing is that they don't look like it's the. Sometimes it's like the story that's being framed about what's happening here. And like, this story is like, one story is. Oh, if I try and I don't get it. Damn, that's just. That hits me, you know, I think that part of the thing is that guys are so accustomed to failure in some way when. Especially when it comes to this. Like, they get shut down so much. Even the most, like, good looking, thorough. He gets shut down too. Believe it or not. He gets shut down more than a lot of women think. And I think that if you redefine the story of, like, looking back or giving a look or just presenting yourself in an open manner or even, just even saying hi, oh, my God. I know. Crazy, crazy theory. But even that is like, when you reframe it to being like, oh, I'm just going to be like a exuberant, nice human being as opposed to, like, trying to, like, get measure every little outcome of your look. Like, that doesn't make a lot of sense because of course you're going to look back at some point and the guy's not going to be looking back. What is that going to, like, put a. A thorn through your heart or something? Like, what's happening here? This is just part of the thing. Right? And like, it's not like women haven't always done this in the past, too. They've given some eye contact, they used to drop the handkerchief. Like, all these things are very real. And would they always work out? No, but that's a part of the interaction between men and women, you know.
I love that reframe. Yeah, you're right. That is not a big L. And I appreciate you, by the way.
I get. Yeah, and I get the fear. Like, I talk. So many women are saying. Women tell me that they don't even look at the guys. They, like, they can look at the guys they're not that interested in, but the guys are interested in, they just totally avoid eye contact with them. And I said, well, I don't understand, like the waffle brain of mine doesn't really get that, but I get why that maybe makes sense for you. But for any guy, like, I don't understand that at all. It makes no sense. And because of. Right. We were talking about before, maybe guys have gotten a little more hesitant to approach girls for a variety of reasons. But you could argue, yes, guys have gotten a little, a little more risk adverse in that sense. But also on the flip side of that, this is not me defending guys because I've met a ton of dweebs and bums and everything else. But on the flip side of that, I have to mention that, you know, when guys are on social just like a lot of girls are, they see a lot of women kind of talking about a lot of men basically saying like, oh, they're putting their hinge profiles up. They're saying, this creep was in this gym looking at me and they get this reinforced into their system and they're like, I ain't going to do that. Fuck that. I'm not putting, I'm, I'm not getting put on her TikTok. So there's, there's, there's this hesitancy with being a little too much where some girls would be like, what are you doing? That happens. Even just saying hi, that happens. Now again, there's a line to be drawn where guys don't know how to come off and they can do some stupid shit. Of course they can. But there is a hesitancy also because of that moment too. Whereas they're fearful of some girl going on and talking about them or, or her entering the group chat. And I, this guy was a creep. So there's the hesitancy there.
Yeah, I think that's, I think that's very, very fair. Meet a different guest each week.
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I asked you to try to find your passion. Okay, so one of the questions that I told you. My girlfriend has questions that she wants you answering.
Oh, shit.
So one of the questions that she was asking about is when a man pulls away, she's been dating a guy for a while and then all of a sudden she's not hearing from a week at a time. What is the right way to handle that and is that normal?
I think it depends. Right. That would really depend on how long we're talking. Like if she's been seeing him for like four months or if she's been seeing him for like two weeks.
She's been seeing him for two months.
Two months. So he starts to pull back. So he's pulling back, like not talking to her for a week. All right. And he was talking to her for more than that before.
Yeah.
So something changed.
Right?
Right. That just means he's losing interest. It means he's lost interest or he's losing interest or he found some. Most of the time that's typically the case when a guy starts pulling back and he's not. And he's. And he. And he had an energy at first and that energy changed for whatever reason. Doesn't necessarily have to be her even. It could just be like, well, I just don't see myself getting down on one knee for this girl. And maybe there's a lot of factors I might. He's not gonna slam the door shut. A lot of guys keep the crack open, but they're not going to like, hey, this isn't working out. It happens, but it's rare. It happens, but it's just not as common. Whereas a lot of guys will keep the door open and sometimes, yeah, they may find their attention going elsewhere. Maybe there's another girl that's taken up their time and energy and they're like, okay, well I don't, I just don't feel her as much. But I'm not going to be like, I don't like you because X, Y and Z.
Okay. So I gave her different advice. Wait, this is so interesting to me. So I was saying to her, in my experience, there's a few things that can happen and I'm super interested in your opinion on this. Obviously is. I think one, something could be going on in his work life, in his business life, with his child, like with his situation that is overwhelming, consuming, negative. And he's letting it negative spiral his life. And so he's not paying as much attention to her and probably other things at the time, but that it might not even have anything to do with her. So maybe that's a time to reach out to him and say, hey, just wanted to check in on you. Like I was going to put your face on a milk carton. What's going on? Are you okay? You know, okay, that's one option. Or could it be that, you know, he. They started getting really close and it freaked him out and he took a step back to say, wait a minute, do I really want to get into a serious relationship at this point? What do you think about those responses?
Yeah, the second one is very valid. I agree with you that he could have gotten really close, but not necessarily freaked out of success, just freaked out of the fact that he like didn't see. He probably didn't see a future there. He's like, I don't want to get any closer because it feels like wrong. But also feels like maybe I should take a step back here. That's possible. The first one. Would you say again, the first one that.
The first one, I was thinking we don't know what, like we want to create a story for people, but we don't really until we ask them. We don't know. He could be in a custody battle right now with his child, that something happened with his ex wife and we had no idea about it. And he feels like he needs to be showing up every day for his kid and he's trying to keep work together at the same time. And he's putting her mentally on a back burner because he thinks everything's fine with her and not even like real. I noticed that sometimes men aren't even aware that a woman's like, what is going on over here? And if you don't communicate something to him to say what's going on with you, he's not going to realize that he took a big step back.
Yeah. And listen, by the way, I don't disagree with that. You know, here's the thing, right? Like, that could always be the case. And depending on the phase of life, depending he has kids. Like, these things matter, right? Like, you're talking about a guy who's like, living in the city at like, 32. You're talking about a guy that's like, has a house and he's 55 or 60 and he has kids. Like, these two different scenarios. And I want to separate those. But either way, right? Let's just say, and this is. This is. This is a classic example, too. So this is good to actually talk about either way this goes, right? We can come up with theories and we can say, hey, this is the reason, and that's the reason, and that's the reason. And maybe some of those are going to overlap to be correct, but who knows until it's communicated? So I value communication. I put it very high. And I agree with you. I think that if you want to find out, go find out. And that means, hey, like you just said, hey, I was going to put your face in the milk card. Haven't seen a while. Like, there's nothing wrong with that. There's just like a fear attached to that. Just like there's a fear of making eye contact with dude. It's like, well, I don't want to. I don't want to not hear from him. Then I'm going to be able to. Then I'm gonna have to sit in my room and just pout for a week because I can't figure out what about. What about me. He doesn't. Like, there's. There's a lot of associations with that story. But either way this goes, you have to have enough kind of like, yes in you to say, okay, let me reach out. Because I'm not. I'm not the guy to be like, oh, just ghost is ass. That's not. I don't. I don't believe in that shit. Like, if you're. Especially if you're starting to talk to somebody and it's been like two months, like, you're already getting accustomed to getting in the routine. What's the problem with communicating? So I'm big on communication, so I don't disagree with actually both of those things. You Said so, like, it could be he lost interest. Could be he's seeing another girl. Could be he's going through something. It could be all those things. And all those things are valid, but unless you, like, are willing to communicate, especially at two months in to figure out what it is, and by the way, you reach out and he doesn't get back to you, or he gets back two days later, you know, you know, and then you can say, okay, well, now I've put my best foot forward. I tried. And now I can. I can just say, okay, well, it's not going to work out, and that's okay. But at least you know that you don't have to live in regret. Like, why didn't I even ask the dude?
I love that. Yeah, don't live in regret.
Don't.
Just don't make up the story to your point. Don't make up a false story that is not true, because that's not fair to him or to you. And then the second thing is, get rid of your past stories and just take the leap and ask so you don't have to wake up and say, oh, gosh, I wonder what happened to that relationship. I'm never going to know. Because then you're not going to learn from it, and then you're not going to be better.
Oh, yeah, big time. Like, you know, for the level of anxiety that a lot of women that I speak to have, their fear of communicating exceeds that. It's like, there's just high level of fear associated with saying something that's going to scare them off. I'm like, what do you think is going to get scared off from your communication? If he gets scared off from your communication, he doesn't like you like that. Like, we have to kind of make decisions kind of in some capacity, right? And like, how could you even move forward without saying to yourself, well, at least I tried. I don't know. You know, I think that's with everybody guys too. If they're. If they have an inability to communicate something and they're not communicating, everyone will just be like, you're soft. What is your issue?
A lot of this seems to go back to confidence and belief in yourself and knowing that if this isn't the right person, that's okay. There's gonna be, if this door closes, a better one's gonna open. There's someone else better out there for me. Is that what you're seeing happen with a lot of these women that's afraid that there's only one, 100?
And this is kind of like in your expertise as well, I'm sure, especially with the confidence building, you know. But a lot of it is that story. And I always go back to that because this is a typical topic that I always hear is like, well, then that means this and that means this. Like, we can all draw these assumptions, but why don't you. There's a story that's attached to the reason why you're not doing something. And I think you need to tell a different story. You need to say, well, maybe, you know what? Maybe I'm going to go and be my best self and I'm going to communicate thoroughly. And if somebody doesn't want to communicate that thoroughly, then maybe that's not for me. There's a more empowering way to deal with this as opposed to just being so fearful all the time. You can't kind of scare a guy that likes you away because you communicate. I just. I don't see that ever happening.
That's so good for women to hear that. I love that. Okay, what if you see women who have been dating, they're discouraged, right? Because you know this. There's not always the greatest guys out there. There's not always the greatest women out there, right? So some people might have some bad dates, bad experiences, and they're just down on dating. Do you recommend that people take a break from it, go back to your regular life, take the focus off. Or do you say it's a numbers game, keep plowing through?
It depends on the situation. But I will say that, like, if you've just gotten your heart broken, that's one thing. Then maybe you need to take a little bit off and like, be like, okay, I need to regain yourself and refocus a little bit. But like, I'm not a big proponent of, like, taking a lot of time off because a lot of people get really engulfed in routines and they get very comfortable in their own routines, and they find it very difficult to now actually do something that's in their favor, that's going to be their benefit, even though they know it's going to be in the benefit. But, you know, when I talk, when I talk about confidence specifically, what I talk about is building momentum within confidence. So I talk about bits of progress, and I always say, stop thinking about the. The big gigantic goal and really start the smallest bit of progress. Example, small bit of progress. Okay, you're an introvert, you're an avoidant, whatever we want to call you, and you're inside, and you have a very difficult time interacting People, small bit of progress is literally just going around certain guys. Small bit, one bit next time, okay? The next time is just. Just literally looking at it, dude. Small bit of progress. And all of a sudden you start to see the benefit of all these small bits of progress. And that kind of starts to build a viable course of momentum for you. And the momentum starts to actually build confidence. But you. You kind of. You don't want to overwhelm people by being like, you got to go in here and look at them and smile on them and stand next to them. They're gonna be like, I'm never do that. But just, you know, just get off your couch. Number one, get outside and just take a walk. Number two, when you see a guy, maybe just stand next to him for a second and pretend. Number three, like, these small bits of progress tend to work, right? And I've worked with women who've been like, I'm just really afraid to, like, you know, I don't want to go out alone or with a friend and actually focus on this. I said, okay, well, you don't have to. You know, you could just. You do what. You do what you want to do. But there's a beautiful thing that many women have said, you know what, Benny? I can't believe it. Actually, I just went to the bar and the story about going to, like, a restaurant, let's just say, for example, there's a story like, I don't want to go to a restaurant and be that girl. I was like, no, no, you're just going to restaurant to have a dish or to grab a wine. You're not going first. You're just placing yourself. You're not even doing anything. I don't want you to do anything. Just go the smallest bit. And then all of a sudden, like, things just start happening because they just have one bit of progress. And then, by the way, not even the fact that a guy comes up to you, a guy can just look at you, and all of a sudden you. A woman who has been out of the dating scene for, like, 20 years. I've worked with plenty of them, but they. They've had this moment where it's like, I don't know how to date. It's so new, it's so different. Just putting yourself in a position where you dress up nice, you go out, you just. You just have a. An hour to yourself out. And you get one look from a guy, and all of a sudden you're like, wow, you know, he didn't do anything. But I kind of, like, the look. And then you go back next time when the guy smiled at me and he was talking to me, but he didn't ask my number. But I liked it. It was really good. Those are the momentum pieces. And I just find that when you overwhelm the story with all the expectations you have, you tend to fall short of all of them. And it's really important to detach from an outcome, but just start getting engulfed in embracing the process of putting yourself in position.
You know what's so interesting to me is when you were just describing that, which I completely agree with, it reminded me you could be talking about finding a job, you could be talking about finding your confidence. You could be talking about starting out at the gym and finding your health. Right. Like, these are universal truths that can be applied to anything and don't have to be so mysterious. It's really the same methodology to create a relationship as it is to create business and create confidence.
Totally. And that's where it stemmed from, like, when I wrote the book. I've been in, like, the startup business world a little bit, but, like, that's kind of where this came from. It was more like, honestly, like, I'm not. I don't say anything innovative. Like, it's really. Sometimes, like, my delivery is a little bit different, but, like, it's nothing innovative. It's very, very, like, fundamental. It's like, very fundamentally basic on, like, getting specific outcomes and kind of getting engulfed in the process and enjoying the moment and having fun and doing those things. And I think that dating specifically for a lot of people is difficult because they've developed a structure around a lot of other aspects of their life, like their work and their school and. And their gym routines. Like, there's a lot of structure associated with, like, you do X, you get Y. And I think that with dating, there's not a lot of structure. A lot of people have this really unique Disney story fairy tale attached to how it should happen. And not a lot of people actually like to think about dating so strategically. And I get it. I get why it's not an attractive thing to be like, oh, what do you mean? I got to do this, this, and this? I'm like, well, you don't have. No, you don't have to do anything. But if you think about it a little bit more strategically, without focusing on the hard truths of the details, just strategically framework, and then, like, think about how to progress that aspect your life. Like, you know, if you don't think about dating or dating fundamentally with more Purpose or more intention then I don't, I don't see how you just expect things to happen. I know no other part of your life do you kind of expect things to happen. And I think that it's kind of like a rewire of like. Well, maybe I need to put some focus on it because dating has changed so drastically over the last decade that maybe it's worth. With the abundance realm of what? Of availability of people online and the attention you get, how do you start to focus that into a place where you can start to get some momentum in dating? To your point, by the way, it's just very fundamental. It's not like anything crazy. No.
And, and I love that because it's doable and you can see how you've done it in other aspects of your life. So why couldn't you do it in this aspect as well?
Right. And I just think a lot of people don't like to think of it that way. That's my point. It's like it's, it's, it's supposed to be romantic. It's supposed to be gray and, and mysterious and undefined and beautiful and not so thought through.
But you're right. If you don't have an intention and you aren't setting that intention and hat and taking some action steps towards it, you could be waiting a heck of a lot longer.
Oh, a lot longer. And like, you know, I always talk about like there's people who operate like leaves, you know, and I, I use this term because like leafs, like whatever way the wind blows, I blow. You know, what are you looking for? Whatever. I don't know. We'll see. And that's okay. If you don't have any wants and desires, not nobody's going to pressure you to want that, but like just nobody wants to hear it later. That's all. We just don't want to hear. I don't know why it didn't happen, but like, you know, I mean, that's all.
Okay, so what is the one piece of advice that you want to leave the audience with. With before we wrap up?
I would say the one piece of advice, if I have any advice, is honestly consume less and have some fun. And I think we've gotten to a consumer culture when it comes to dating advice and getting input from people online and friend groups and you're, you're overly bombarded with information when it came, when it comes to this aspect of life and it's kind of paralyzing people and it's making people very fearful and scared. And you know, one woman asked me on a podcast before, she said, well, you know, why should women listen to us? And I don't think they should. Matter of fact, they'd be better off just not listening to anybody and just going to live their life and having some fun and without overcomplicating all this. Because the more you consume, all of a sudden everything becomes a problem. You're overanalyzing everything. But I heard online. What do you have to say about that? I don't have anything to say. Just go live your life. How about that? Just don't listen to anybody. You'll be so much better off. Like part of my stuff is like I don't even when I take my one on ones I don't get you on I one time with you. I don't need anymore. We don't need to do this every week. If you want to, fantastic. But this is not, this is not what I'm doing here. Reframe it a little bit and then you go live in life. Don't over complicate this.
I love how simple your advice is and this is what I take away from this conversation is listen to you over everything.
Have fun.
Just go out, have fun and live your life. Have some intention on what it is that you are looking for. Listen to your own self and take chances. Don't be afraid and stop overthinking. I mean it sounds so simple. Hopefully we can all put it into motion. Ben, tell us, how can people join your groups? Where do they follow you? How can they find you?
Yeah, I appreciate that and thank you for summarizing it up and actually beautifully said. You can find me at Benny Inc. B N Y inc. On Instagram, TikTok and I have a dating with purpose community that anybody can sign up for. Some it's a subscription but anybody can sign up for it on my website, bennyheart inc.com and that's it.
Well, thank you for the work that you are doing to bring more love into people's lives and encourage them to believe in themselves and have more fun.
You're the best at it. Thank you.
All right, guys, until next week. Keep creating your confidence. You know I will be. I decided to change that dynamic. I couldn't be more excited for what you're gonna hear. Start learning and growing. Inevitably something will happen. No one succeeds alone.
You don't stop and look around once in a while. You could miss it.
Come on this journey with me.
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