Dating Intelligently 2: Older Men Struggle With Modern Dating

Author(s): Scott Douglas Jacobsen

Publication (Outlet/Website): The Good Men Project

Publication Date (yyyy/mm/dd): 2025/07/09

Christopher Louis is a Los Angeles–based international dating and relationship coach and the founder of Dating Intelligence. As host of the Dating Intelligence Podcast, Louis draws on intuition and lived experience to guide clients toward authentic selves and meaningful romantic connections. Louis discusses the challenges men in their forties and fifties face in modern dating. He highlights the allure and pitfalls of dating younger women, the undervaluing of women of the same age, and the need to shift male mindsets toward emotional maturity, shared values, and compatibility. Through personal anecdotes and coaching insights, Louis emphasizes that long-term fulfillment comes not from superficial attractions but from reciprocal, emotionally intelligent partnerships. His new platform, Mentality, supports men who are ready to find meaningful relationships with confident, successful women who are closer to their life stage.

Scott Douglas Jacobsen: Once again, we are here with the charismatic and socially astute Christopher Louis. Today, we’re focusing on men in their forties and fifties. This demographic can present unique challenges in the dating world. The reasons are not always obvious, and even the apparent ones benefit from a more nuanced perspective, which you consistently bring to the conversation. You’ve been watching a new television show featuring Mad Men actor Jon Hamm recently. What’s the show called, what’s his role, and what’s the early narrative?

Christopher Louis: The series is called The Morning Show, and it’s available on Apple TV+. Jon Hamm joined the cast in the third season as Paul Marks, a wealthy tech billionaire who becomes involved with the network’s leadership and media operations. His character is ambitious, calculated, and represents a new wave of Silicon Valley-style influence entering traditional media spaces.

While the show is not directly about Wall Street or a man’s struggles with family life, it does explore themes of power, generational transition, and ethical compromise—all issues that resonate with men navigating midlife and career shifts.

That said, I’ve also been thinking about how many fictional shows portray men in their forties or fifties who seem to “have it all”—success, relationships, status—but are still deeply unfulfilled. A typical character arc often starts with the man living in a modest situation, rising through his career, building a family, and yet constantly feeling the financial and emotional pressure of keeping it all together. Despite professional success, a sense of personal meaning often lags.

In one dramatized scenario I saw recently—not from The Morning Show, but in a similar genre—a man in his late forties meets a woman in her late twenties at a bar. She initiates the conversation, flirts, and he’s flattered but cautious. He responds with, “You’re way too young for me,” and then walks her through all the reasons why their age difference would lead to tension over time.

He imagines the first few months going well—they connect, have fun, and feel the spark. But then he projects ten years ahead: he’s in his late fifties, she’s in her late thirties, and their life stages have diverged. She remains energetic, socially active, and eager to spend time with friends. He wants peace, comfort, and wine nights at home. He predicts that she will eventually want someone closer to her age—someone more vibrant, physically compatible, and ready to live that faster-paced lifestyle—while he retreats into slower rhythms.

This touches on a larger point: many men in their forties and fifties, especially those who have been divorced or in long-term relationships, often seek out younger partners. The fantasy is one of companionship, vitality, beauty, and new beginnings. However, reality usually leads to mismatched expectations, varying energy levels, and differing emotional needs. These generational disconnects typically emerge over time, complicating what initially felt like an escape or a second chance.

Usually, it’s women in their late twenties to mid-thirties. The reason why is that, after divorce, many men tend to shift toward wanting someone—what’s the term?—hotter, younger, sexier. They want someone who appears to have a more promising life ahead of them.

They often look for someone who doesn’t share many commonalities with them, but they don’t mind. They’re thinking: “I have money, I’m successful, and I can take her on trips, show her the world.” That’s the mentality. That’s what the guy I mentioned earlier was saying in the show.

So, fast forward—I just started a company called Mentality. It’s a platform for men in their forties and fifties who want to date women of a similar age. I prefer not to use the phrase “age-appropriate” because it feels dismissive. What I like to say is: you want to find the right fit for right now.

That means men who are open to dating women within about a ten-year age range—either a bit younger or older—but more importantly, women who align with where they are in life. It’s not about age as a number; it’s about stage of life, mindset, and values.

There are so many women out there today—strong, independent, fit, successful—let’s call them alpha women. Women who are leading businesses, who don’t need a man for anything. And yet, these same women are finding it hard to meet men in their forties and fifties who share their mindset. Why? Because so many men in that age group are chasing the younger model.

What I’m trying to do is help men see that they can find incredible women in their age group—if they open themselves up to that possibility. Women in their forties and fifties who are confident, accomplished, and share the same values are what they’re looking for.

Instead of going younger, which often leads to mismatches in priorities—like wanting kids or still being in a party phase—men can choose partners who are on the same page. Maybe they’re both done having kids. Perhaps they’re both ready to travel, relax, and build something meaningful together. That alignment is powerful. However, the challenge lies in changing their mindset.

That’s the hard part—reprogramming that mental narrative. Encouraging men to recognize that successful, emotionally mature, and vibrant women do exist in their age group. These women share their values, their ambitions, and their rhythms. But many men don’t see it because they’ve been conditioned to believe that these women are “too old” or “out of the game.” And that couldn’t be further from the truth.

Jacobsen: So it’s not about what’s missing in these women—it’s about what’s missing in the way men are seeing them.

Louis: Absolutely. That’s the core message I’m trying to push. These women are right there. They’re not lacking anything. Men have been taught to value youth over alignment, and that’s what I’m working to shift.

So, I want to let these guys know—they’re entirely wrong. Once again, there are many incredible women across the country and the world who share this mindset. But what I keep seeing is this belief among men that, once they’ve dated someone their age, they think, “I don’t want that again.” And why? Because they say, “She knows too much.” They feel these women will tell them things they don’t want to hear—things that challenge them or hold them accountable. And that intimidates them.

Jacobsen: I did look it up. According to a 2023 report by the Pew Research Center, which analyzed U.S. Census Bureau data, there’s now a record share of Americans aged 40 and older who have never been married. One in four 40-year-olds today—up from one in five in 2010. So the other category, not included in your comments so far, is men who aren’t divorced but have never married. Do they have the same mindset?

Louis: Men in their forties and fifties who have never been married often exhibit a distinct mindset. Honestly? Many of them exhibit a Peter Pan syndrome. They never really want to grow up. They could date someone their age, sure, but they’re rarely satisfied.

I know several men in this category. Good friends of mine. They’ve told me straight up, “Chris, we love you—but we just want to date younger women.” And the reason? They don’t feel secure enough—emotionally, physically, or mentally—to date a mature woman who is confident and has her perspective.

They worry they won’t measure up. They feel like mature women won’t find them desirable, or will challenge them in ways they aren’t ready for. So, they default to dating younger women because it feels easier. They believe they have more to offer a younger partner than they would to a peer, whether that’s financial security, experience, or a more desirable lifestyle.

Jacobsen: What are women saying to you—especially those from other industries or social circles—that reflect these patterns you’re describing?

Louis: Many women in their forties and fifties are saying the same thing. This is verifiable—you could look it up right now. There’s a significant portion of single women in that age range who are struggling to find a partner. And the number one reason they give? Most men their age are only looking to date younger women.

So, these women already feel left out and dismissed. They’re vibrant, successful, emotionally intelligent, and often in the best shape of their lives. But they’re not even being considered because of this widespread male mindset that says, “Older equals less desirable.” That’s not just unfair—it’s untrue.

Louis: And so now, a lot of these women are adjusting their dating preferences. For example, a 40-year-old woman might start looking at men in their late fifties or even sixties—older than she ideally wants—because the pool of age-aligned men has shrunk. On the other hand, women in their fifties often trend younger. They feel they have a lot to offer a man in his forties or even thirties.

And for some younger guys, there’s this Mrs. Robinson vibe—a sense of novelty or excitement around dating an older woman. They think, “I’m dating a cougar, this is exciting.” It can also become a kind of fantasy dynamic, where the older woman takes care of him, not because she’s trying to, but because she naturally brings a maternal presence. It’s not always healthy, but it’s real.

Jacobsen: That’s a whole different psychological layer—and maybe even a whole other interview series. However, you’ve identified the core of the issue as changing the mindset of older men. In many ways, it sounds like the old saying: teaching an old dog new tricks. So, how do you do it?

Louis: The best way for me to start is by helping the guy clarify what he’s looking for. When I ask that question, they’ll say something like, “I want someone who’s emotionally stable, shares my values, is active, supportive, and communicative.” And then I ask, “Do you think you could find that in a woman your age?”

Most of the time, they say yes. But when they go on a date with someone their age, they come back and say, “I just don’t think we had enough in common.” And the underlying issue? The truth is that most men prioritize physical appearance above all else. They ask: Is she attractive? Is she in shape? Is she aging well? These are the top three filters before they even get to shared values or emotional compatibility.

I recently had a client who went on five dates with a woman of the same age as him. She matched him in values, lifestyle, and long-term goals. Initially, he said she was fit, attractive, all of it. But a few dates in, he started nitpicking: “She’s a little saggy here,” “a little baggy there,” “some wrinkles.”

So I reminded him: “But you said she shares your values, you enjoy her company, and you have chemistry.” And he said, “Yeah, but…” And then the fundamental shift came. He told me she had started to boss him around a little, and that turned him off.

On their last date, which started great—they were laughing, connecting, everything was going well. Then she said something like, “You should start wearing nicer shirts,” or “You’d look better if you shaved that beard.” Something simple, but it triggered him. For him, it crossed a line—he felt criticized, managed.

This is where it breaks down for many men. They want a partner, not a parent. But they often misread confidence or directness in a woman their age as being “bossy,” when it’s just someone who knows herself. The next time they went out, she said to him, “I want to go to a place like this, not that last place you took me. That place felt low-rent.” And that hurt his feelings.

To him, that earlier place was special. However, she had a mindset that it wasn’t good enough, and she made it clear that she wanted something more upscale. He felt like she was discounting his efforts—not validating what he was trying to do—and that she was becoming pushy, even bossy, steering the dynamic into territory he wasn’t comfortable with.

That put him off. So I told him, “Maybe you need to tell her—calmly and clearly—that you didn’t appreciate the way she said that.”

She’s probably, once again, what we’d call an alpha woman. Someone who’s used to being in control—maybe a bit of a ‘boss bitch,’ to use the colloquial term. He knew that about her going in, but it finally showed up in a moment where she let him lead. And when she disapproved of his choice, she made it known in a way that felt dismissive.

I felt that was unfair. But to his credit, he did call her out—gently. I advised him to say something like, “That wasn’t what I was expecting, and I didn’t appreciate the way you said that.”

And to her credit, she responded well. She said, “Oh my God, I am so sorry—I didn’t mean to hurt your feelings. I’m just so used to leading, taking charge, and being in control.”

That right there—this pattern—is one of the biggest turn-offs for men in this age group.

Jacobsen: Do you think, in contemporary society, people are reevaluating what they want from relationships, and that this is part of a broader cultural experiment? We’re seeing more empowered, professional, self-sufficient women now than we ever have, globally. Could that be contributing to these kinds of jarring relationship dynamics?

Louis: That’s correct. In today’s world, many women are used to leading, especially in their professional lives. However, when it comes to dating, what I hear from many of them is, “I just want a man who takes the lead.” And they don’t mean that in a toxic or hyper-masculine way.

They’ll say, “I’m such an alpha in my business world. I want to be able to step back and have a man lead for once.”However, when a man tries to lead, some of them struggle to relinquish that leadership mindset. They end up unintentionally undermining his role.

And I tell them, “Look, that’s going to happen—it’s natural. However, you must work together to strike a balance. If you want a man to lead, and he steps up to do it, you have to let that happen without jumping in to correct or control everything.”

It’s about trust. It’s about resetting the dynamic so that both people feel respected, and both can relax into their respective energies.

Louis: But even then, some people still complain—”This isn’t what I expected,” or “This isn’t how I would’ve done it,” and so on. In those moments, you have to have the confidence to say, “Look, I hear you, but we need to find a balance. I don’t appreciate you discounting what I’m doing just because you think you have a better way.”

If you want me to take the lead, let me take the lead. That requires trust. You can’t say you want someone to lead and then undercut them every time they try to do so. It’s about mutual respect.

It’s the same with men. Many women say, “This guy, it’s his way or the highway.” And I tell them: Then you have to speak up early. Let him know—”I don’t appreciate that. I need to have boundaries. You need to respect what’s good for me and us. It cannot be about you constantly overstepping those lines.”

It’s like you have to teach each other how to find that balance. But most people are afraid. They’re so scared to speak up. They’re so scared to assert themselves.

And what happens? They end up in a relationship where the other person always takes the lead, and they lose their sense of self. Man or woman, it doesn’t matter. If you don’t speak up from the beginning, you lose your footing. You lose your balance. And the relationship never feels equal.

Jacobsen: Once men start making that mindset switch—even just a little—how does that play out in their dating life?

Louis: You’re right on point, Scott. Seriously. That’s the question. And it’s funny, because once men even slightly shift their mindset, the dating experience starts to change in significant ways.

A friend of mine once said something to me that stuck. I’ve researched this extensively. I’ve been speaking with men now in their sixties, many of whom are currently dating women about ten years younger. But here’s the thing: when I first met these guys—right after their divorces—they went much younger. Like, significantly younger.

So I started asking them, “What changed?” I spoke with several of these individuals, who are now in more age-aligned relationships, and one of them put it perfectly. He said, “Chris, let me tell you the truth.”

He goes, “When I got divorced, all I wanted was to have fun. I wanted a sexy girl. I wanted much sex. I wanted to go out, travel, do whatever I wanted.” And I said, “That’s fair.”

He replied, “Yeah—but then I realized I had nothing in common with these younger women. Once I figured that out, I felt ready to date someone closer to my age again.”

And that shift was key. He eventually met a woman who was about ten years younger—within that healthy range—but more importantly, someone with whom he had a high level of compatibility. He ended up marrying her.

He said, “Now I feel like I’ve found harmony. I was ready to reset, to get back out there—but I also knew what I wanted and what I didn’t want.” And this new relationship reflects that balance.

The woman he married is successful. She has her career and financial stability. She doesn’t need him, but they thrive together because they push each other to be better. It’s an equal, reciprocal relationship.

In contrast, when he was dating those much younger women, he felt compelled to do everything to impress them. He was taking them on trips, paying for everything, essentially taking care of them. And eventually, he got sick of it. He told me, “I don’t like this. I’m tired of carrying the whole thing.”

And I said, “Well, yeah—that’s what happens when you’re dating women who are still trying to establish themselves in life or business. They’re not there yet.”

Now, in his marriage, his wife doesn’t need him for anything, but she wants him. And that’s the difference. They challenge each other, yet they support one another. It’s a good set—an intense match.

So, what I try to teach men in their forties and fifties is this: if you trust me and are genuinely looking for someone authentic—someone who shares your values and is leading a parallel life—you can find that. And the good news is, the women I work with through my matchmaking company aren’t looking for someone to take care of them. They’re looking for a partner.

And the men I’ve matched with these women so far? They’re blown away. They’re like, “Wow.” She’s a beautiful woman—not only on the outside, but also on the inside. And being younger or older isn’t the point. It’s about finding the best fit for me at this time. That’s what I’m trying to do. If more men could just let go of the mindset that says, “I’m in my fifties, so I want a hot girl,” we’d get somewhere.

I ask them, “What do you mean by that?” They usually say, “Someone I can go out with, have much sex with.” And I respond, “Okay, but then what? After that? What are you looking for next?”

Most of them say, “I don’t know. I haven’t thought about that.”

So I press them: “What values do you want in a woman—if you say you’re ready to settle down?” Because the kind of woman they’re describing is not someone they’re going to build a life with. That’s a fleeting experience. Six months, a year—then it’s over. Then they’re asking themselves, “Why did I even date someone like that?”

So why not shift your mindset? Say instead: “I want a woman with high emotional intelligence. I’m looking for someone who shares my values. Someone who will walk with me through life, not control me, but partner with me. Someone who’son the same journey.”

If I can get them to understand that, then I know they’re ready. That’s when I know they’re prepared for the next level. That’s precisely what I’m trying to help them achieve through my company.

Jacobsen: What about the category of men who get divorced, don’t want a relationship, and still reach out to you? Is your advice to say, “Well, that’s what you want—go hire an escort”?

Louis: The good news is, most of the time, the men who come to me aren’t in that category. The guys I work with are ready to settle down. They’ve already been out there, done the whole song and dance with younger women, lived that experience, and now they’re looking for something real. Ask any dating coach: when a man in his forties or fifties reaches out and says, “I need help,” that usually means he’s ready.

Jacobsen: And what about the flip side? The ones who aren’t ready?

Louis: I’ve seen that too. I’ll reach out to a guy about joining the company, and he’ll say, “Chris, I think what you’re doing is great. I love your mission—but I’m just not ready yet.” And I always respond, “You know what? I appreciate your honesty.”

When you’re ready to join—or when you’re prepared to change your mindset—come to me. We’ll be here to help with whatever you need. Most guys, more than women, need to go on their journey. A woman often already has a clear mindset about what she’s looking for—even if the path she takes is not always the right one.

Jacobsen: What do you mean by that?

Louis: I mean, a woman usually says: “I want to settle down, I want to get married, and I want to have kids.” That’s typically the checklist. But a man? He’ll say, “I just want someone who’s physically and sexually.” So I ask, “Okay, and after you have that, then what?” They’ll respond, “I haven’t thought that far ahead.”

At least women, even if they go through 50 guys, still place their hopes, dreams, and values in finding the right one. They believe in the possibility of alignment. They think, “This guy could be it.” Whereas many men place their hopes and dreams into someone who excites them sexually—often someone younger—because she’s keeping them physically stimulated and making them feel alive again.

It’s almost like when a woman has a baby and enters that euphoric “new mother” phase—what do they call it, baby bliss? That rush of emotion that makes everything feel perfect?

Well, when a guy is sexually active with a younger woman, he gets a version of that same emotional high. He puts on those goggles and thinks, “Everything is amazing.” But when that phase wears off, what’s underneath it? What’s left?

So I always say: at least women start with their values. They may get disappointed, but they’re on a consistent emotional path, trying to find someone compatible. Many men have to go through the whole circle—realizing that the younger, purely physical relationship was a mistake—before they say, “Okay, I’m ready to find a real partner.”

Jacobsen: Do you think part of that is because women, as they get older, typically have richer social networks? Is it that they’re communicating more with their friends, cross-referencing and learning from each other’s experiences?

Louis: Not always. However, women do tend to discuss relationships more with their friends. They receive input, undergo emotional processing, and engage in group reflection. Men don’t do that as much.

But look—this starts young. Let’s be honest. You can ask an 18-year-old girl what she wants in a relationship, and she’ll often say something like, “I want a man who’s successful, who’s confident, who can be the man of the house. I want to get married. I want to have kids.”

Meanwhile, an 18-year-old guy? He’ll say, “I want someone hot. I want to have fun. I want to work on my career.”

Jacobsen: So the developmental tracks are already split early on.

Louis: That divergence stays with us. And unless men do the work to evolve their expectations—to move beyond the superficial—they’ll never build the kind of relationship they say they want once they hit their forties or fifties.

At that age, guys are thinking, “I want a successful career, I want a fun girl, I want lots of sex, and I want to date as many women as I can.” That’s not a typical mindset for a woman at that age.

As time passes, however, women’s mindsets evolve differently. A woman in her thirties—especially if she’s still single—starts thinking, “My biological clock is ticking. I haven’t met the right guy. What am I going to do? If I’m not married by 35, what happens next?” Suddenly, there’s a kind of internal alarm going off: “I don’t want to be the woman who’s single with three cats, living alone.”

So, even though women often talk to their friends and reflect together, the pressure they feel can lead them away from what they truly want. They lose sight of their core values because now it’s about urgency. It becomes, “Let me just find someone who fits well enough right now.” However, even if they marry that person, he may not be the right match for them.

And later, as they get older, they realize, “I made a mistake.” But by then, they feel it’s too late. Perhaps their career stalled, or they lost a part of themselves.

Jacobsen: So they stay in a bad relationship simply because of inertia.

Louis: Inertia. It’s emotional survival mode. 

Jacobsen: Let me briefly address the issue of younger women dating older men. Say a woman in her mid-twenties is dating a guy in his fifties—what’s going on there? What’s the thought process?

Louis: Okay, so not all of them, but many younger women who date significantly older men are, in some cases, looking for what I’d call a “quick fix.” I hate to use this term, but it’s a sugar daddy dynamic. Someone who can support them while they figure out their career or next steps in life.

There’s a real phrase floating around now among their peers: “Why not find a guy who can take care of you while you figure out what you want?” That’s the actual advice some of them are hearing from friends. And honestly, most guys are okay with it, because both parties are getting their needs met. Let’s just be honest.

A 50-year-old man dating a 26- or 30-year-old woman thinks, “I’m dating this gorgeous younger woman.” Unless he’sGeorge Clooney or Brad Pitt, he’s just thrilled that she’s even in the picture. Meanwhile, the younger woman might be happy to have someone taking care of the financial side of things. And here’s what ties it back to what we said earlier—on dating apps, for example. When these younger women go on a date with an older man, they’re not shy. Many of them will outright ask, “Can you buy me something?” Direct expectations.

It’s become normalized. They’re confident about what they want. The social taboo of asking for something upfront? It’s fading fast in this dating culture. What happens is, early on in the dating process, some women will say things like, “Hey, I’m a little behind financially right now,” or “I probably need a little help—do you think you could help me out?” They’re not afraid to ask for that kind of support early, far earlier than they would if they were dating someone in a traditional way over time.

Jacobsen: So people are generally becoming more practical—maybe not in terms of a complete, fulfilling life picture—but in terms of knowing what they want and going after it. And that spans across age, sex, and gender?

Louis: Correct. People are becoming more direct, more pragmatic. But at the same time, we can’t forget that there are still plenty of traditional people out there—men and women—who want a conventional marriage. They want to fall in love and have that simple, stable life.

That’s why I did a podcast episode on this. I called it “Dating Differences and Age Gaps.” I featured a couple with a 23-year age gap—he’s in his sixties, she’s in her late thirties. They’ve been together for over ten years. And honestly? They’re a perfect fit.

She’s an old soul. He’s a young spirit. They complement each other beautifully. So yes—some people buck the trend. I’mnot saying it’s impossible. It can happen. But it’s rare. It’s far and few between.

Jacobsen: What should we end on?

Louis: It’s a broad and interesting topic—too vast to cover in one conversation. But I’ll end on this:

Let’s go back to the beginning of time. The age gap between men and women in relationships has long been a prevalent phenomenon. Historically, it was normal. A 30-year-old man would marry a 14-year-old girl—not because it was emotionally mature or ethically sound, but because she was young and fertile. That’s what society, especially royalty and traditional systems, valued—fertility and lineage.

It goes back to kings marrying girls 20 years younger, sometimes even teenagers. As long as the woman could bear children, that was the determining factor. The younger, the better—because the more likely she was to produce healthy heirs.

That was the logic of the time. Thankfully, society has changed, but remnants of that mindset still linger in how men, even today, subconsciously view youth and fertility.

But the context now is different. For example, a man who already has children may not be looking to start over and have more kids. The genetics are the same, but the mindset isn’t. A man who has already had children with his former partner usually doesn’t want to do it again. He’s done with that chapter. Now, he’s often looking for a partner, not someone to start a new family with.

Jacobsen: Thank you for the opportunity and your time, Chris.

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