Creating Confidence with Heather Monahan
#520 What He’s Really Thinking in the First 3 Dates: Flirting, Communication & Navigating the Early Days of Dating with Dating Strategist Ben Hart
Tue, 13 May 2025
If you’ve ever felt like dating is one giant mystery while every other area of your life has a strategy—this episode is your game-changer. I’m joined by dating strategist Ben Hart, and we’re breaking down how to stop sitting on the sidelines and start approaching your love life with the same intention, confidence, and momentum you bring to your career. From how to stop overthinking early dating stages to setting standards without pushing love away, this conversation will help you flip the script on dating and attract the kind of relationship you actually want. In This Episode You Will Learn Dating requires intention, just like any other life goals. The small confidence-building steps that matter more than grand gestures. Why creating fictional narratives is killing your relationships. Practical tips for flirting and navigating the early stages of a new relationship. Stop treating dating as a transaction, enjoy the process and yourself. Resources + Links Sign up for a one-dollar-per-month trial period at shopify.com/monahan Download the CFO’s Guide to AI and Machine Learning at NetSuite.com/MONAHAN. Want to do more and spend less like Uber, 8x8, and Databricks Mosaic? Take a free test drive of OCI at oracle.com/MONAHAN. Get 10% off your first Mitopure order at timeline.com/CONFIDENCE. Get 15% off your first order when you use code CONFIDENCE15 at checkout at jennikayne.com. Call my digital clone at 201-897-2553! Visit heathermonahan.com Sign up for my mailing list: heathermonahan.com/mailing-list/ Overcome Your Villains is Available NOW! Order here: https://overcomeyourvillains.com If you haven't yet, get my first book Confidence Creator Follow Heather on Instagram & LinkedIn Ben on Instagram
Chapter 1: Who is Ben Hart and how did he become a dating strategist?
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, 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 of 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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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, whoo,
Ben is also the author of The Zero Mindset, A Transformative Guide to Creativity and Reinvention. With a background in psychology and biology and advanced training in 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 they truly want in life and relationships.
Ben, thank you for being here today.
Thank you, Heather. You're just, you know, the way that you hype it up, you're just such a stage person. I love it.
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Chapter 2: What are the biggest challenges women face in dating after the first date?
Yeah, for sure. And that takes some time sometimes with people, right? Like different people have different, the way they absorb that kind of pressure or perceived pressure from society or their close circles. Yeah.
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? To give you an example, I have 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, I 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 age.
OK, 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, 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 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
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Chapter 3: How should women handle attachment and storytelling in early dating stages?
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 the 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 things. It's 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 with these two big issues that you're seeing?
Well, 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 that qualify a guy showing interest 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 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 of them 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
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Chapter 4: What is a situationship and why is it important to avoid long ones?
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 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 situationship, kind of.
So not having the 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 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 into Harvard.
You can't say, once I get into Harvard, then I'll change. No, it's 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 I'm 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 behaviors that are not conducive for long-term success inside a 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 fuckery shit that I – excuse my language, that I always see happen. And then blame the guy because he was a narcissistic, manipulative dude.
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Chapter 5: How can women communicate commitment needs without pushing partners away?
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Chapter 6: What are the differences in dating dynamics for women in their 30s?
Chapter 7: How important is self-accountability in attracting healthy relationships?
Well, 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 that qualify a guy showing interest 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 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 of them 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 past proximity, eye contact, smile.
So those are the kinds 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 one. And sometimes, yes, I advise getting a little flirty, but 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're vetting him, too. And sometimes people forget that. They forget that once they choose, they think, oh, 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 day 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 going to 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 think that a lot of women that I speak to, a lot that are 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 to first date. Which is like, well, what's going to turn on? Why did I just turn her off?
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