“The Man Up Show” – How Older Men Can Date Younger Woman

Man Up | Ep. 118   •   June 15, 2016

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For over a decade, David Tian, Ph.D., has coached tens of thousands of people from over 87 countries to achieve happiness and success in their dating and love lives.

Once a nerdy, skinny professor of Asian philosophy who couldn’t hold a conversation to save his life, David is now director of Aura Transformation Corp., and a world renowned dating and life coach. Dr. Tian has been featured in international media, including AXN, Cosmopolitan, Psychology Today, as well as co-hosting a radio show on national radio and a weekly dating advice column in a national newspaper in Singapore. Formerly a professor at the National University of Singapore, Dr. Tian is actively researching, speaking, and publishing in the areas of philosophy and psychology.

The show, “Man Up: Masculinity for the Intelligent Man,” is David’s way of helping as many people as possible enjoy empowering and fulfilling lives, while contributing to the global understanding of masculinity in modern times. In the show, he takes your questions posed in The Man Up private Facebook group and answers based on his experience Coaching tens of thousands of students around the world for over a decade.

David’s also prepared free video courses that reveal how to get a new girlfriend, how to make friends anywhere, and how to talk to anyone. Click Here and scroll down the page to access these free resources.

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David Tian: Boom! Stop. In Episode 118 of Man Up, I answer the question of: How an older man can date a younger woman.

[MUSIC] Masculinity for the intelligent man. I’m David Tian, Ph.D. and this is Man Up!

Hey! It’s David Tian, Ph. D, and for the past ten years, I’ve been helping tens of thousands of people in over 87 countries find success in life and love. And here I am in Bali. Just wanted to show you this incredible view from the balcony. Will let the camera there adjust. This is the Intercontinental. Originally picked it because of the location by the beach, as you can see, but they have an incredible pool. In fact, we’ve been at the beach so much that we haven’t even made it to the pool yet.

You can see, if you look closely, you can see the ocean. Beautiful property, and they’re playing gamelan music all the time, and there’s a look at The Intercon club lounge there, the balcony there. And this is just the center courtyard. There are at least two other courtyards. This is a really big property, but beautifully sighted. And here’s the balcony. If you’re smoking a cigar at night, but it’s kind of hot so I’m going to go inside. And we’re in a duplex suite, pretty cool, huh? Goes up there.

Okay, close this thing, lock out that gamelan music with this. Alright, okay. So, I’m trying to hold this steady. Answering a question sent to me through private message. I don’t normally answer private message questions. I prefer they’re asked in the forum, but it started in the forum and then he wanted to give me more details in the private message. So, it’s forum and private message, or Facebook, I should say, and private message. What’s the name here? Let’s see… It is from Xavier. Xavier says, “Here’s my story. I’m a 52 year old guy. Regular looks, not overweight and in reasonable shape, recently divorced. I haven’t been on the market since I was 20.”

How to Attract Younger Women

I’m going to lock the light here so I don’t get some weird thing going on in my face… Okay. “Since I was 20,” he says, so he hasn’t been dating since then… Before marriage, he had sex with four to five girls. So he says, “My dating and sex experience is very limited.” I’m going to move this way… “Lately,” he says, “I’ve been dating and rarely sleeping with older women all over 40. Women with huge personal issues,” he says, ‘huge’ is in all caps, wall-to-wall inhibitions, women with years of emotional and/or physical baggage; women with messed up bodies and minds. And to be honest, I don’t want that.” He says, “Being and considering my old age, I desperately look for much younger women, women in the 25 to 35 age range. Women who are fun to be with, women who are emotionally healthy and sexually open to such a relationship.”

So he says, “I want to break that circle in which I, as an old man, am ‘allowed’ to date or sleep only with women over 40. I want to make it in succeeding with younger girls, as in dating and sleeping with them.” And then I asked him a further question, “What strategies have you already tried to improve your dating and social life?” And he says, “Besides social dating,” by which he means meeting women through friends or social circles, “I still haven’t tried anything else.” Okay, so he gives us an idea of what’s happening here.

Okay, Xavier, I’m going to give you the quick answer. So, I’m going to move backwards from my answer instead of starting from the root and moving forward, I’m going to move backward because I find it’s how the human mind works. So, your biggest issue comes at the very end. It’s interesting how, if I continue to ask clarifying questions, usually the problem underlying, like the deeper problem surfaces, and here’s the deeper problem. And there are deeper problems than this, but this is the first deep problem.

I asked him what he’s tried already and he says, “Besides meeting women through friends or social circles”, he hasn’t tried anything else. Well, that’s your problem. So, if you’re recently divorced and you’re 52 years old, your social circle is not going to have women who are much younger than you. Unless something strange happened there, but probably your social circle will be within ten years of your age. You’re 52, so 42 roughly, in their 40’s, which has been your experience.

How to Date Younger Women

And in order to meet women who are open-minded and all these things that you mention, you’re going to have to go outside your present social circle. So, if you keep confining yourself to what you call social dating or meeting women through your friends, you’re not going to find women like this. So obviously, you’re going to have to start being more social and stepping outside your comfort zone.

Where to Meet Women

So, there are a lot of places where you can. I’m going to give you an example. One of my best friends, he’s 52, and we’ve been friends for over seven years. Currently, the last I heard, he’s dating a woman who’s 22 and another one who’s 28. A few months ago, he was dating a girl who’s 19, who was cheating on her boyfriend with him, and he felt bad about that eventually, just broke that off. But he’s 52, so this is pretty common for him. And he hangs with us regularly so one of the things he likes to do is go to places he enjoys. Obviously, people like to go to places they enjoy, and he happens to enjoy craft beer bars, which have become really popular among the 20 to 30 year old crowd.

So, he likes craft beer bars and women there tend to be more open-minded and intellectual, or at least they think they are, or they enjoy intellectual talk or pseudo-intellectual, and they’re open more to talking to strangers at a craft beer pub. If you don’t like to drink… I don’t know more about you than what you’ve said here in your message, so I don’t really know what other preferences you have. But I know guys in their 50’s, who date much younger, who are into Latin dance and they go to social dances. So, it’s socially acceptable there to be an older man dancing quite close with a younger woman.

They do social dances. So, my good friend, at the beer bar, he meets women there. He didn’t learn any techniques or tricks, he just talks to people and is very social. In fact, he’ll talk to women at cocktail bars. He likes to go to those, or like grown-up bars, where you’re not going to find an 18 year old. Well, sometimes you do, but they’re generally not going to be there. But 25 years old is right in the middle of that market, craft beer and fancy, like a mixologist cocktail bar, those are great places to meet that age range that you’re talking about, 25 to 35.

Meet New Friends

People there are generally more open to conversation. They’re not going to be jumping around dancing, and there’s usually no dance floor, and there’s usually no DJ and the music is not super loud. So, that’s the first… The easiest thing, you could also do a yoga class, you could do a cooking class. Basically, find out where are the women that you’re interested are, and go there and pick the places that you would enjoy yourself, even if there are no women there, that you’d still enjoy. That’s really, really important. Don’t go there just to meet women.

Places to Meet Women

So, pick a place you enjoy that also has women in this age range. If that doesn’t exist, then you have to broaden your interests and try new hobbies and new things, like maybe trying new cocktails or something. I don’t even know what town you’re in, so maybe it’ll just be craft beer bars. There are a lot of those in the US and all over the world. I mean, my friends in Singapore. But just getting there, that’s one thing. The second thing, is you have to have the skills, or the confidence, and the emotional intelligence to be able to start conversations with people and have it pretty natural, and then naturally exchange contact info and naturally follow-up. If that doesn’t come naturally to you, as it doesn’t for most people, then take a course.

So, that’s what we do at Aura Transformation. Sign up for any of our free courses. We also have much more, bigger courses that run up to 60 plus hours. And then of course, we have life coaching as well. So, there are a lot of different levels of knowledge and practice that you could do. So, there’s that. So, you get the skills, go to the places. But even then, and this is something that would be covered in any of our programs, you still have to work on yourself. So, one of the things about my 52 year old friend, is that he’s quite vigorous physically.

So, you couldn’t tell, no one guesses… Probably because he hangs out with people… And I’m almost 40 by the way. I’m turning 40 this year, and when you’re older and dating younger, you’re always doing the same sort of thing, but he just does it even more because he’s that much older, which is that you want to look younger. So, one thing is, I just shaved, so shaving makes me look younger. Having a younger haircut makes me look younger, keeping in shape… So, my 52 year old friend doesn’t wear trendy clothes because that would just look ridiculous on an older guy. It looks like he’s trying too hard, but he wears casual basics when he’s out.

And when he’s at work of course, he’s wearing his dress clothes, but when he’s out on a casual getting-a-drink with us, he’s just wearing casual clothes. So, those are casual clothes that make him look ten years younger just by the clothes themselves. And then the way he carries himself, you wouldn’t be able to tell he’s 52 until he has to read something. And then he’s got to pull out his glasses and does that. And then you know, “Oh wait, what’s going on?” But other than that, he looks like he’s in his early 40s, looks 10 years younger.

A big part of that is that he’s physically active. So, he motorcycles for fun and does long distance motorcycle trips. He does scuba diving on a regular basis. He travels a lot. Like, when I’m in Bangkok, he might just message me two days before and just pop, “Hey man, you in Bangkok?” and then pop in for the weekend, just to hang out and get some drinks and stuff. So, he’s leading a pretty fun lifestyle and that keeps him excited and young, and without a whole lot of baggage as you’ve been talking about here – and carefree.

So, he does stuff with his fashion, he does stuff with his physical activity to keep him vigorous, and then of course there are all the other grooming. Like, have a good skincare regimen, and drink lots of water, and eat healthy and all of this. That’s all stuff you can see a dietitian for or a fitness coach to get you physically vigorous. You should also be doing things that test you, that kind of scare you a little bit but also excite you. Example are… If you’ve never ridden a motorcycle before, that would probably do it when you’re first starting out; things like that. Step outside your comfort zone, it’ll raise your testosterone levels. It’ll make you feel younger again.

Taking up new hobbies, those are all good to make you feel younger again, give you that feeling of newness. And also, obviously, put you in front of new people and force you to be more social and meeting new people as a way of life. So, don’t ever get stuck. Ossified is the word. Don’t ever get ossified in your current social circles or your friend’s circles. Always be looking to test yourself, and challenge yourself and broaden your horizons. That’s also a masculine type of energy as well and you want to dwell in the masculine energy if you want to attract younger women.

And especially the type of women you don’t want, those are going to be women who – even if they were feminine at their core – have now gone into their masculine, which have created these inhibitions and baggage and so on. Whereas you say, “Messed up bodies and lines.” Okay, so you should develop your masculine energy, especially now at 52; anything that will raise your testosterone, any activities like that are good. But then even further is your mindset. So, I’ll get back to my example with my friend who’s 52, exactly your age. Who’s pretty care-free, easy going, but also likes to push himself, doesn’t take himself too seriously, laughs a lot, really casual.

Oh, the other thing is… “You know, I just came back”, so along these lines of the mindset which is most important. So, mindset and then fashion, fitness, activities, and then learning your social intelligence, developing your emotional intelligence, and then actually going to the places where they are. So, those are the different steps. As I said, I’m going backwards. So then, finally, the mindset and… I was just at an academic conference where I was giving a keynote talk. I was the only non-full-time academic there. I’m not making any money from it. I actually was in a position where I was losing money by being there because I was away from running the academy.

But I enjoy it so much, and a lot of them are my old friends. We went through school together, grad school and so on. So, I love it. It was like a reunion. And what I notice is, when you become an academic… Academics, they take pride in being counter-cultural in a nerdy, old man way. So, even if you’re in your 20s, there’s an identity attached to being an academic which is like slouched over, glasses, physically unfit, skinny, spends all his time in the library around dusty books, even though now technology totally makes that obsolete, but there’s still that identity.

And one of the things that they do is… Very few of them actually have Facebook profiles. Or if they do, they’re not active. Actually, most of them don’t. Even my age, they don’t have Facebook profiles. They’re not on social media at all. It’s like a point of pride for them. But what that also tells me is, they’re not in touch with the young people, which is fine if they don’t give a shit about that, that’s fine. But you, as a 52 year old, trying to get around 25 to 35 year old women, you’ve got to understand their world. Otherwise, even if you get around them physically, like you’re in the same room with them or in the same bar or whatever, you’re not going to be able to connect because you have nothing in common mentally, and that’s the most important thing.

And so, you got to learn their world. And don’t limit yourself to your way of thinking. The biggest thing that prevents older men from dating younger women is not the physical, because that can all be dealt with; that can all be improved through fitness and fashion, and getting a good fitness coach or something like that, and getting a good dietitian and just working hard for three to six months and getting there. But the hardest part is the mindset, the hardest thing that’s really keep older men from dating younger women is the mindset; the mindset of when you meet them, you don’t connect.

So, the fact that you are connecting, I mean your social circle is full of women in their 40s, which is normal, is… Like, I don’t connect with women in their 40s. That’s just one of those things and it’s not something I’m working to do or am concerned about doing. So, I’ve given up on that; I don’t really care about that. But a lot of guys who do, they then don’t connect with women in their 20s because those are very different worlds, actually. And I’m forcing myself, I have to force myself, because of my clients, to understand men my age who have gone through the normal things and have not lived the kind of lifestyle I and my friends live. So, I have to enter into that world in order to serve them, but it’s my job so I enjoy it.

But I have to do it consciously, I have to see it as a conscious process where I then have to read what they’re reading, watch what they’re watching, go to the places they go, understand their daily routine and enter into that mentally so that I can go there with AR and then see them from where they’re at; which is partly what I’m doing for you now, even though I only have like three or four paragraphs which I’ve written here to go on.

But then, you need to do the same thing if what you want to do is make friends, and date and hook up with younger women, you need to understand their world. What their needs are, what their desires are, what they think about, what they listen to, what they read, what they consume, the content they consume, the food they consume, the places they go to, their influences; you got to learn all those things and you have to approach it like an academic subject, like, you really do have to learn it.

And not just to learn it, but to appreciate it, like you’re learning to appreciate art. Maybe there’s some art you don’t enjoy, but you then have to learn to appreciate it, if that’s what you want; dating these women. Because even if you were to just get their bodies physically, which you can just pay for that shit, you’re not going to be able to connect with them emotionally and that’s what seems like you really want. And in order to connect with them emotionally, you’re going to have to enter that world in your mind and in your heart. So, one of the things my 52 year old friend likes to do is… He’ll go on a club, and maybe it’s kind of loud for him – I think he’s starting to lose his hearing anyways – but it’s kind of loud.

I mean, that’s one of the biggest complaints, or excuses I should say, from older guys who are trying to get their social lives back together. Is now they go back into the youngsters’ world, and it’s loud, and dark, and there are lots of people drinking, and they’re just confused because they’ve been in the world of sitting in their study room after changing diapers or something for ten years. You know, or being by themselves or having tea every day instead of going out and having some fun and letting loose.

And luckily, he hasn’t had to go through that because he’s regularly in those settings, and I think he has trouble relating to women in their late 30s or even mid-30s into their 40s. He has trouble as a 52 year old guy because he doesn’t give a shit. He doesn’t care about that world. He’s into the younger world, which I find that more exciting myself, so it’s more natural for me as well.

Okay, so, those are the four different areas, right? So, I’m going to go forward now. Get your mindset right. That is, you got to learn that world, you’re in marketing or something, you got to learn your market, and get inside their heads to understand their world so that you can connect with them. And then work on your fashion and your fitness, fix that. Fix your social intelligence, social skills, your emotional intelligence, and then finally you got to go to the places where they are and befriend them. So, as you’ll learn in step three where you’re learning social skills, not just befriending the women but their whole social circle.

So, you got to make friends with their guy friends, or their brothers or whatever; whoever they hang out with. You can’t just pick them off. Then again, you can. My 52 year old friend, he meets some of the girls he dates as they’re walking down the street and he’ll just stop them and ask them some directions thing and then just actually… “I was really just interesting in getting to know you.” And he does that sort of thing completely untutored he just does that, just because he found that it works and does it.

So, you can do it like that too; cold approaching. So, I’m not going to limit you on social circle. But anyway, you got to get the skills and try to be cool. You got to fit in. If you want to date her and not just hook up with her, you have to be able to fit in with her social circle. That means, you’ve got to visually fit in better. I mean, you’re never going to completely fit in and that’s good, but you want to be… It’s not going to cause so many problems or questions to her. Like, “Why are you dating this grandfather?” You don’t want that. So, you got to fit in, you got to look cool.

But here’s one more thing I’m going to end off with. As an older man, you have a huge advantage. I don’t want you to just think, “Okay, now I have to be younger and everything.” You do have to, on the surface, look that way, and to be able to enter that world, mental world, yes. But then, you bring along without all of your emotional maturity, all of the things you’ve gone through, and your… At 52 years old, you probably don’t give a fuck about a lot of the little shit that 20 year old people freak out about. You have perspective. You realize it’s not that big of a deal and you can be calm more about the situations that arise that young people freak out about.

And you have perspective, that’s the most important thing that you can bring. So I’ll give an example. A young guy might start talking to the girl you’re with, or at a house party or something and then he’s being funny and doing a lot, sort of like a pick-up artist type, doing a lot kind of talk. And then maybe she’ll turn to you and say, “Hey, this guy, Derek,” I’ll just take as an example, “Derek said this and this and that. What do you think?” And you can just, as an older man, look at him like, “Don’t be a dick.” or “Stop spouting nonsense to young girls, come here.” You just have more of an authoritative tone because you are older, you’ve earned it, you’re just more senior so what you say just goes if you say it authoritatively.

So, take ownership of that leadership role that you now have as an older man. Woah, it’s 20 minutes. I was hoping it would just be seven or eight. I think the key to making this shorter is to limit the question, the scope of the question, because as you can see… One of the biggest problems is, somebody thinks that what they’re looking for is just like one or two lines, when that’s the problem in itself. The fact that they don’t understand the problem is the problem. So, now you’re starting to see how to fix this problem, it’s a much bigger thing. It’s not just like… I can even give him superficial advice.

“Just go to the places they are”, and end, right? But that’s not going to solve the problem. He’s got to go all the way back to the root of mindset and intelligence. Okay, cool. So, join the private Facebook group. You can ask me your questions there. I’ll answer some of them right in the group, otherwise I’ll make this episode for you. You can also correspond with me through private message, but I really expect you to write in the Facebook group first and that’s the first point of contact. So until I see you there, Man Up!

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