Dating Coach Mark Sing
← The Unapologetic Man Podcast

Episode 664 · May 8, 2025 · 22 min

How and When to Show Maturity, Refinement, Connection, and Chivalry to Women

About this episode

Once men learn that being the 'nice guy' doesn't work, they usually get led down the path of being the bad boy. They'll be playful, banter with her, bust her chops.

While this is important when it comes to getting her attracted to you, it's not the complete picture. You need to know when and how to be mature, to let her know that you can be serious, chilvalrous and respectful.

The key is balancing these elements together with the banter and playfulness. In today's episode, Mark breaks down how this whole dynamic works so you'll know exactly when to stop the jokes and be serious with her. Apply for Mark's 3-Month Coaching Program Here: https://coachmarksing.com/coaching/

Check Out The Perks Program: https://coachmarksing.com/perks/

Follow Mark on Instagram: https://www.instagram.com/coachmarksing/

Watch UMP Episodes on YouTube: https://www.youtube.com/channel/UCybix9PZoDgcyyt5hNxPLuw

Grab Mark's Free Program: "The Approach Formula": https://www.CoachMarkSing.com/The-Approach-Formula

Contact Mark Directly: CoachMarkSing@Gmail.com

Read the full transcript Show

So, I was driving down the road with my girl the other day, and she turns to me, and she's like, are you even listening to me? And I think to myself, that's a weird way to start a conversation. Welcome to the Unapologetic Man Podcast, the only podcast that's all about self-improvement, confidence, success, women, and being a man without making any apologies for it. What is up, gentlemen? Happy Thursday. Thank you for tuning in to another episode of the UMP. And today, boys, we are going to talk about how and when to show chivalry, refinement, maturity, trust, and connection with women.

This is something that gets a lot of guys blown out. Usually not the biggest reason they get blown out, not the biggest reason they get put in the friend zone, but it's the biggest reason you get labeled as a player or one of the biggest reasons that guys get left in relationships. So in this game, you have to have game, right? You have to know how to flirt with girls. You have to be interesting. You have to make them laugh. You have to intrigue them, build on their emotions.

But at the same time, you have to build what I call trust and connection, the T and C rule. So we're going to talk about how to be chivalrous, how to be mature, how to be refined, and how to actually build that trust and connection in today's episode. And make sure to stay tuned until the end because I got a lot of good shit to drop in your lap today. So trust and connection is exactly as it sounds. It's you're building a relationship with a girl.

You're building trust with her. You're showing her that you're ultimately real. Now, the problem with most guys, and I see this all the time with guys who are dating girls on a first date or guys who approach a girl on the nightclub, is that this is pretty much all they do. They try to build rapport. They try to build commonalities. They try to get in that connective space with her, showing vulnerabilities too soon, trying to talk about deep things too soon rather than being playful. So the reason why I dedicate the majority of my podcast and frankly, the majority of my coaching program on how to flirt and how to elicit emotions is because in that first conversation, that's 80% of what you want to do.

80% should be flirting, generating emotions, telling stories, making her laugh, busting her chops, push, pull, cold reading, false disqualifiers, all the stuff I teach. But 20% should be getting to know her, showing your vulnerability, showing that you are mature, refined, and that you can be chivalrous. So the problem for most guys is they default on that. They want to get to know her. When they have a commonality, they like give her a high five. They get really excited about those things that her and him have in common.

And because of that, they don't build enough emotions. So we understand how to build emotions. At least if you've been listening to my podcast for a long time, you have some understanding of how to do that. Now I want to talk about how to be real, how to be refined, how to be mature, and show her that you're not just a clown. Because oftentimes when you guys hear my methods, such as, do you like to travel? And she says, yes. And you push her and you say, travel over there.

Immediately, especially for those of you guys who are kind of stuck in this logical, super mature viewpoint, you think that's being childish. And what I have to say to that when guys accuse me of being immature, because I am 48 years old. And a lot of guys are like, dude, you're teaching guys how to like do these immature, playful, juvenile kind of things. You're immature, Mark. My answer to that is this. Attraction is immature. Attraction is playful. Even if you take an 89-year-old grandma and an 89-year-old grandpa who both happen to meet each other in the retirement home, there's going to be a level of playfulness there if they're building attraction.

Attraction is based on being playful, having emotions like kids on the schoolyard. So yes, it can be said that sometimes my techniques as well as other pickup artist coach techniques are somewhat immature, but it's playfulness. So you can label it as playful. You can label it as immature. What can't be denied is that that's what builds attraction. The reason why I rarely record episodes like this one where we do talk about being mature and being refined is because a lot of you guys default to that too much in the first place, which is why I spend the majority of my time trying to get you to the other side.

Like, dude, be more playful. Be more random. Don't give a shit about what happens. Have fun like two kids on the schoolyard. Bust her chops. Give her shit. Tease her like you guys are in second grade. Pass notes back and forth. Accuser of certain things. Role play like you guys are just kids. But again, the maturity, the refinement does need to be put into it, but it's in very small percentages and it must be calibrated as we're going to talk about today. So in that first conversation, 20% you're being real.

Now, being real is honestly what you're probably an expert at already. It's building commonalities such as, oh, you went to that college? So did I. That's crazy. I didn't know you went there. Did you ever notice that this college XYZ thing and you guys are building a commonality just like if you meet a dude and you're trying to make them your new friend. So you're building commonalities, you're laughing about things that you agree on, you are being agreeable to some respect, and you're also showing vulnerability.

Now, as I always talk about in this podcast, when you show vulnerability, you want to do so showing that you either got over the thing or you have the solution to get over the thing. As an example of this, I had a conversation recently with a girl where we were talking about our dads for some reason. And this was the first conversation. I was being playful. I was teasing with her, telling her stories. We were having a really good time. And something came up about her dad and how her dad recently passed away.

Well, my dad passed away when I was 10 years old. So instead of like joking about it in an immature way and being like, oh, what happened? Your dad got unceremoniously launched out of a catapult into the Atlantic Ocean. I'm socially savvy like that. So what I did is I took that opportunity to tell her about how my dad died when I was 10 years old and how a year earlier before he died, he invested a lot of money into me playing football. But I quit playing football, telling him instead I wanted to play soccer.

And literally the week before he died, he said, you're not going to stick with soccer. You're going to quit just like you quit football. I'm disappointed in you that you quit football. You're going to quit soccer, aren't you? So when he died, I like got obsessed with soccer. I went way overboard with it to kind of like prove to him that I could stick with something. But even to this day, I never want to quit anything because I don't want to like let my dad down as he's looking at me from above.

So what I did is her telling her story about her father dying and her relating to me how it has motivated her. I took that as an opportunity to show the maturity, the refinement, the trust and connection. And I use that moment, sprinkling it in 20% into the conversation to show her that I can be real. Once again, the problem with most of you guys is that's your whole conversation. You're like 80-20, the opposite direction. You're 80, trust, connection, maturity, refinement, because you think the other 20 of being immature is immature and it's going to blow you out.

But guys, attraction is playful. I wouldn't even call it immature. I would just call it playful because that's what it is. You have to elicit emotions. Girls love to laugh. Girls love to be teased. They love to have that mischievous look on their face as you and her share a little secret from the rest of the group. You could call it immature, but really what it is, is playful and playfulness builds attraction. But at the same time, if you don't have enough trust and connection, she's not going to sleep with you because she doesn't know that she can trust you.

And this happens to a lot of guys who get into this niche because they learn all these cool techniques. They start getting confident with NLP and things I teach like declarations and they start really feeling like that pimp and they know how to spit game, but then no girls want to sleep with them. The problem is they're not putting in enough of that chivalry, enough of that maturity, that refinement, that trust and connection, which is done, as I just told you, by talking about real things.

For example, when I first ask a girl's name, I'll say something silly. Some of you will say it's immature. I say it's playful. I say, so, hey, what's your name? Let me guess. Let me guess. Your name's Sha Dynasty, isn't it? And she'll be like, no, that's not my name. I'm like, oh, really? What's your name? And she's like, Amy. I'm like, what's up, Amy? I'm Mark. Nice to meet you. And I'll shake her hand in a real genuine way. I'll show that I'm real. I'm the guy who she can invite over to meet her mom.

You need to throw some of that in there. How much? 20% in the first conversation, in the first date. You could push it up to 30%, kind of depending on how she is. If she's like a really serious girl and she isn't as playful as you kind of wish she was or that you're usually used to, you can push it up to 30%. But dude, if you do too much of this, it's going to get you blown out because she's going to say that you're boring. Here's female psychology 101.

She's going to bring up boring shit. And if you run with it, she's going to blame you for boring her. For example, she brings up the presidential election and you guys spend an hour talking about the damn presidential election, having no flirting, no playfulness, no stories, no gamuts, no push-pull, no cold reading, nothing. And you're just like mature and refined. And you're talking about your vulnerabilities and how scared you are that Trump is going to start World War III. She's going to say, hey, it was good to meet you.

Take it easy. You're going to be like, oh, I thought we had this great connection. You did, but you didn't have enough flirtiness and playfulness. So there's always a time for maturity, refinement, trust, and connection. But boys, literally 30% at the most in the first conversation, first date. Then the second date, you could pop it up a little bit more. You can go 30%, 40%, 60%, 70% playfulness, flirting, telling stories. And by the way, that 70%, it's not all being playful and silly and joking and like, ooh, the whole time. It can also include psychological tests.

It can also include you mentoring her. All the techniques that go into what I call value, which is one of the four pillars of attraction that I teach my boys, frame, control, value, sexual attention, and qualifying. Value is basically what I'm talking about. But there's also that 30% to 40% trust and connection on the second date. Third date should be about 60-40. And then fourth date and beyond, it's about 50-50. So even in my own relationship, I tease Marissa. I mess with her. I tell her funny stories.

I crack her up. She always says there's no lack of laughter in this household. And I love how she says that. But the other 50%, I ask her things like, how was your day today? What do you think about that new babysitter we got? What are you feeling about your new business that you're opening? I show that maturity and refinement because you have to have that balance. Now, when you guys are talking to women, typically, you're pretty good at doing this already because really, it's just building commonalities.

Oh, you like sushi too? So do I. High five. That's pretty much it. But it's also showing vulnerabilities, as I talked about. And when it comes to vulnerabilities, don't forget, you have to either have a solution for something that you're struggling with, or you overcame something that you struggled with previously. An example of that is I used to have anxiety. NLP helped me completely overcome it, as well as my agoraphobia. That's building trust and connection with maturity and refinement. But it's showing that I overcame the obstacle.

If you bring a girl a problem without a solution, she will lose attraction for you because of it. So most of you guys are good at doing that, but I want to give you a few hints. So first of all, we understand that this trust and connection, this maturity and refinement, and I'm going to talk about chivalry in just a second, this is all basically encapsulated into 20%, ideally, of your first conversation. It's building the commonalities relating to the person, getting to know the person as more than just somebody who you're messing with at a nightclub or at a party or on a first date off Tinder or whatever it is.

So what you're doing is getting to know them, asking them questions, telling them things about yourself, being real, being mature, being the dude who, again, she would like to introduce to her mom. That's what we're doing here. Certain questions you can ask her to get her to kind of be more real with you, more mature with you, build that trust and connection, involve the old reporter trick of how, what, when, why. When you ask questions in this format, she's going to give you more than just like a yes or no answer.

She's going to give you more depth. So, for example, let's say she's a nurse and you're like, oh, that's cool. What made you want to become a nurse? How did you get into nursing? Why did you choose to become a phlebotomist, for example, as opposed to working in the oncology unit or something like that? So you're showing her that you're interested in what she has to say. You're real. You want to actually get to know her. And when you tell her about yourself, as an example, telling her what you do for a living, that whole 80-20 thing that I just explained actually works in to one of the techniques I teach, which is the three-part answer when she asks you what you do for a living.

There's a three-part answer. The first part is a joke. So she says, what do you do for a living? You say, I'm a penguin valet. The second part is the real truth. I'm actually an NLP coach. And then the third part is there to build trust and connection. You tell a story about how you became what you are, showing yourself overcoming vulnerability, overcoming challenges. So asking those questions in the who, what, where, when, why format is really powerful. And also asking her things like, what would you do with no chance of failure?

What would you do if you had $90 million? Do you have a ghost story? Who is the most important person in your life? What's your favorite book you've ever read? Where would you go right now if you could just leave and travel anywhere in the world? This builds that trust and connection. You relate to her with your own stories. And guys, listening to women in a way that makes them feel heard is so stupidly simple. But most guys, unfortunately, get inside their own head or all they're thinking about is getting into her underwear rather than just shutting the fuck up and letting her talk.

Today, Marissa and I were driving. Didn't really feel like talking. I felt like she did feel like talking. So I asked her a bunch of those questions. I asked her, so what's going on with the construction at your new business? And then she goes on and on. And I just sit there, wrinkle my eyebrows, stare at her mouth and say, uh-huh, oh, really? And occasionally, pair it back to her what she said. She's like, oh, yeah, the contractors haven't got their permit yet. And I'll be like, permits?

And she'll be like, yeah, we got to get permits to build out the building so they can build my business, blah, blah, blah. Meanwhile, I'm just sitting there trying to get rid of my own thoughts, letting her vent or talk or discuss whatever her goals are, her dreams, whatever she's working on. And she feels like she's been completely heard. So building that trust and connection means just being real, showing her you can be trusted. Say you're talking to her and there's like a lot of traffic coming by and she keeps getting bumped.

Maybe you would move spots with her so she could be more comfortable as you get bumped because you can take it. And this works into chivalry. When walking to your car, I always open the door for her when her door is kind of in my path. So if we're walking up to the car and we happen to come up to the passenger side, I open the door for her. If she's cold, I'll give her my jacket. If I observe that she's tired or she's feeling sick, I'll be like, hey, let's get you home.

Or, hey, let's get you this kind of food because it settles your stomach. You're basically just being attentive to her. And as I talked about at the top of the show, this is a big reason that women will leave their husbands is because the wife feels like the husband doesn't listen to her. He doesn't care about her. He's not cognizant of her hopes, her dreams, her struggles. And he doesn't seem there emotionally. Remember, women are emotional creatures, which, by the way, started in tribal communities because as all the guys were hunting, all the women were back at the camp building relationships.

She wants to connect with you. She wants to feel that you're real. She wants to know your hopes and dreams. She even wants to know what you fear, but obviously you have a solution for that. She wants you to know what she fears. She wants you to know what she struggles with. She wants you to know who she is so that you guys are connected, bonded, more than just attraction building techniques and playfulness, as I call it. So you have to have that mixture, brothers. You have to be playful, but at the same time, real.

You have to not give a fuck, but at the same time, kind of be chivalrous. You got to be the bad boy, not to be fucked with. This guy is the alpha of all alphas, but at the same time, you have to be a little bit sensitive and listen to her. Not too much now, only about 80-20 in that first conversation, but just enough. And once again, it goes 80-20, first conversation, first date, then about 70-30 on the second date, 60-40, third date, 50-50 in your entire relationship.

So whenever I would have a girlfriend, I would honestly feel that they would think I was a bad boy, but at the same time, I can listen to them and understand them. But they couldn't quite get me because of the 80-100 rule I always talk about, right? Like you always leave them wanting more. They couldn't quite completely have me, but when they did have my attention, I just laid it on them like a spotlight and they felt understood and heard, and then I would just be out of their grasp where they couldn't fully have me because my life is first, my ambitions are first, she's a second place, if not third place, but at the same time, I want her, but I don't need her.

And it's that balance, guys, that you got to get down. So for those of you who aren't getting sex, this could be a big reason. You're not building enough trust, connection, maturity. You're not like refined enough. You're not showing enough chivalry. And it could also be the reason that a lot of you guys have been blown out either in your relationships or in your marriages. You're not there. You're not present. You have to be cognizant of what she's going through. You have to at least pretend to understand her and at least pretend that you care about her struggles, her dreams, her troubles.

Then she's going to stay with you. Women, of course, are very complicated. A few episodes ago, I did an open letter to women talking about how simple men are, how to keep a man happy. To keep a woman happy is complicated, boys. And that's why I've dedicated, what is it now? 664 episodes to this shit, trying to teach you guys. But this oftentimes is the missing element. That maturity, that refinement, that chivalry, that trust, that connection. How much do you put in? About 20% to 30% in the first conversation.

Just be real. All you guys can do that. Be chivalrous. I know you guys know how to do that. And build connections with her, which honestly, most of you dudes are experts at to begin with. The problem, as I mentioned, is you do too much of that shit. So still do it. Don't get rid of it. But just take it back a little bit to about 20% to 30%. And when you do it, really be there. Like if we're on a smoking patio and I'm talking to a girl and she's cold, I'll move her over to the space heater and be like, hey, you look like you're a little cold.

Let's move you over here. Those little moves, as I'm joking with her and busting her chops and teasing her, telling stories of becoming and mentoring her, really build a lot of attraction. So boys, don't forget this all-important element. It's kind of like salt on your steak. When you add that shit to the steak, it becomes a million times better. But if you forget it, the steak is kind of lackluster, isn't it? It just doesn't taste as good as it does with the little sprinkling of salt on that thing.

So that's what we do with maturity, refinement, trust, and connection. And boys, don't get it twisted. Even if you're older, don't think that what I teach is mature. Instead, label it as playful because women want to have fun. Going back to that ridiculous, stupid, annoying Cyndi Lauper song, Girl Just Want to Have Fun. That's true. And you absolutely must make them have fun and have emotions. But at the same time, you have to build trust and connection. Because if they don't trust you, they're not going to want to have sex with you.

They're not going to want to be your girlfriend. They're not going to want to introduce you to their mom. And they're definitely not going to want to marry you. And if you're married to a girl and you lose that trust and connection, you lose that with-it-ness that you need to have in your relationship, she's going to leave you. And this is probably a big reason a lot of you guys have been left. So I hope this has helped you out, boys. I do appreciate you listening.

Please stay tuned for the next episode. I'm going to talk about eye contact. It's going to be an eye contact masterclass. You definitely don't want to miss it. So please stay tuned on Monday and I will see you in the next episode.

This transcript was made automatically, so a few words may be off.

Want faster results?

Work with Mark 1 on 1

The podcast gives you the ideas. My 3-month coaching program rewires the programs in your head so you actually use them.

Learn about my coaching program