20’s vs. 30’s: Picking Up Women


I want to talk about how the aging process affects your game.

How is it different for a 20-year-old compared to that of a 40-year-old because I started this about 20 years ago almost back when I was around 20 years old. Now I’m nearly 40 years old, so I’ve had the unique perspective of experiencing the game and approaching women and meeting girls in my early 20s, in my late 20s, in my early 30s, and now my late 30s.

There are a couple of differences that happen to you physically and mentally, some actually quite positive and help you out. So you can actually as a guy in your late 30s, if you’ve been at it, you can do much better than a guy who’s in his late 20s.

But there are things to watch out for. There are negatives that crop up that you have to plan against and prepare against if you want to keep doing this well into your 40s and 50s.

The first factor as you get older is you have to walk a more narrow path of good habits. First of all, if you are eating poorly and you’re not exercising, and you’re drinking and you’re not getting enough sleep. If those happen over decades, it’s going to really wear your body down.

You’re going to feel terrible. You’re going to develop fat all over your body. You might have a beer gut. You’re not going to feel motivated and going out to approach girls and meet girls, and do well with the women is going to be completely off the table because you’re going to feel like shit. You’re not going to be motivated, and you’re not going to feel entitled to have these pretty girls.

But more than that, even if you walk a narrow path of really good habits and you’ve got your nutrition down. You’re eating clean foods. You’re going to the gym religiously and keeping that testosterone levels up, and you’re getting enough sleep so you feel good and you’re not putting drugs into your body.

But let’s say that you step off of that path for a week, or even for a couple of days, you go on a vacation and you just drink too much. You stay up really late and you don’t get enough sleep. You’re not going to the gym and you’re not eating right because at the resort, there’s like buffets everywhere, junk food or fatty food.

Well, a couple of days into that is really going to throw you off. You’re going to feel completely discombobulated, and you’re not going to feel motivated any longer. After maybe just one or two days, then you’re going to need days more of recovery just to get yourself feeling normal again.

Whereas if you’re 20 you don’t have to walk as much of a narrow road of good habits. You can drink and then wake up the next day and still be good to go. You could maybe not get enough sleep, and the next day still be good to go. You don’t have to necessarily be working out because your body is naturally producing muscle and testosterone on its own whether you’re working out or not, which is not the case when you’re 40.

By the time you hit 40, your body is not naturally producing that much testosterone anymore. You’re not naturally producing new muscle mass anymore. Your body, it’s default state is just to put on fat.

It takes you longer to recover when you step off the path of good habits, and you’re going to be more discombobulated when you do so.

As you get older, your path to actually do well and feel well becomes narrower and narrower and tighter and tighter.

The second thing that happens as you get older is you become more entrenched in wanting comfort, in seeking comfort,  and not pushing your comfort zone.

When you’re a young guy and someone is like, “Okay, go approach 10 girls.”

You could be like, “That sounds risky and the adrenaline pumping and I’m up for the challenge. I’m just really pushing my comfort zone.”

You are going to be more apt to embrace that compared to when you are say 40 years old, you are more inclined to be like, “I’ll just sit in a chair. That’s more comfortable.”

There’s a couple of reason for this. One is just habits built over the decades. For example, if you start off in your 20s, it’s always choosing the comfortable path. “Yeah, I could approach girls, but it’s just easier to play video games. Yeah, I could hit the gym, but I don’t know I’ll just be comfortable and watch a movie.”

You have decades of that building up. You’re training your brain a certain way to take certain kinds of actions until it just becomes second nature not to want to push your comfort zone, but it goes a little bit deeper than that. I think there’s a genetic component as well.

If you are a young guy in your early 20s, biologically because you’re so young, you wouldn’t have accumulated much resources or status in the tribe. Maybe you don’t have a girlfriend yet. You wouldn’t have had kids yet. You wouldn’t have had time to have houses, or property, or whatever it is, or much status.

It would be in your interest to take more risk, to push your comfort zone that’s going to attract a young female to you. You can become a young warrior, which is a risky business, or go hunting. That’s also very risky.

You’ve got all that testosterone pumping through your veins that’s going to make you take risks. But as you hit 40 years old, in the tribe most likely you would have kids by then or you would have had a couple of wives by then or you would have had accumulated resources like your own hat, or your own fur skins, or whatever it is.

You would be more inclined to want to protect what you’ve already built up. You’re not going to have as much testosterone flowing through you that’s going to push you to take risks. Instead, you’re going to want to just lock down what you’ve already have and not push your comfort zone. You’re going to become scared of change more.

Whereas the young guy, “Cool change. That would be awesome. Maybe some of the older guys will die off. Maybe the status order will get shaken up and I can rise on top more quickly.” You might be more inclined to embrace change.

But for an older guy, not so much. The older guy is more about seeking comfort, not pushing his comfort zone, not wanting anything to change, and that’s going to affect you in the game.

As you become older, what’s going to happen is, “Should I go out and meet girls? It’s just easier to stay home. I don’t want to rock the boat. Should I try to build a harem of girls? Just easier to not rock the boat and stay home. I don’t want things to change. Do I have to change what I’m doing? Do I have to change something about my identity? Do I have to work on myself? That’s a lot of effort. I’ll just not do it. I’ll just prefer to be comfortable.”

That kind of sneaks up on you more as you become older. A lot of times guys become less flexible, and they get steeped in these habits of not taking the right actions.

That’s a trap you really have to watch out for. But just that awareness where you realize your brain, your unconscious brain is telling you just be comfortable. Don’t take risks. Don’t take push yourself.

No! I’m not going to let that happen. I’m going to take right action despite what my unconscious brain is telling me. I’m going to do it no matter what.

What does this mean if you’re a young guy in your late teens, or early 20s, or mid 20s, what conclusions can you draw from this?

First of all, if you’re thinking to yourself, “Yeah, I want to start my off business and travel the world but I got to do that later. I got to put that off.” Or, “Yeah, I want to be approaching girls, but that has to come later at a future time.” Or, “Yeah, I know I need to get my health under control. I want to put on some muscle and lose the gut, but that’s going to come later.”

Okay, you might have reasonable arguments for putting things off but the thing that you have to understand is that it’s not going to get any easier for you as you get older simply because your brain is going to be more entrenched in wanting to conserve resources and not take risks and not push the comfort zone. As you get older, you have to walk a tighter and tighter path of good habits just to stay at a baseline normal level.

When you’re younger, that’s the easiest time to embark on new adventures, that’s the easiest time to take new risks both physically and mentally. If you put it off, if you wait, it’s just going to get increasingly difficult for yourself.

The other thing to keep in mind is that when you are younger, it’s always easier to change direction because you haven’t built up decades of negative habits. If you wait to do something until you’re mid 30s or you’re 40s like you actually want to start hitting the gym and getting physically fit. You might want to do that, but it would be really hard to execute it because now you’ve got decades of habits behind you where you were thinking, “Okay, I should hit the gym…nah! I won’t do it. I’ll just prefer comfort. I’ll prepare to relax and watch some television. Yeah, I should approach girls but…nah! Forget it. It’s just easier to stay home, play games, and be comfortable.”

You have decades of making that decision, and it becomes almost like this unconscious part of you because it’s so reinforced over hundreds of instances so that by the time you’re in your 30s or 40s, you’re really out of shape. You’re really sloppy, and you’ve really dug yourself deep in this habit hole that’s almost impossible to dig yourself out of. It’s always better to establish your habits when you’re young, as young as possible, which means you want to establish good habits like right now today.

Even if you don’t have time to approach girls like a maniac ‑ and that’s something you want to do in the future ‑ you can still carve out 20 minutes a day to talk to one or two girls on the bus or the train, or on your campus, going for a walk, at work, or maybe going out a couple of nights a week, just to kind of build up that habit, build up that right action of taking the right decision and establishing those neural connections in your mind when you’re young so that it feels easy and normal as you get older.

It’s not uncommon where I’d be on a one-on-one boot camp with a young student and it’s great that he’s taking action. It’s great that he showed up. It’s great that he’s pushing himself, he’s pushing his comfort zone. But at the end of the day, he’s kind of ambivalent to what he’s doing. He’s really passive in his approach.

Me, a lot of times, he’s skinny. He’s not working out. He’s eating the wrong kinds of foods, pounding back pizza and hamburgers because he’s got a fast metabolism when he’s young and he can still handle it, but he might be drinking and have some other bad habits under his belt.

I’m telling him, “What the fuck are you doing? This is only going to get more difficult as you get older to change. It’s not going to get any easier to change than it is right now. You want to establish good habits when you’re young, so that you can keep going into your 30s and 40s, so o that what you’re doing is sustainable. So that your testosterone levels remain high and remain sustainable into your 40s, so your sex drive and your motivation to meet girls remains sustainable into our 40s, so that you’re constantly pushing your comfort zone when you’re young, so that you are in good habits to constantly push your comfort zone when you get into your 40s.

That’s really important to establish right now, as early as possible, as soon as possible. This is something you kind of work on immediately and don’t slack off just because you’re young, just because to a certain sense you are invincible because when you are young, yeah you can walk as much as sloppier a habit’s path and still feel motivated, still feel good, still feel healthy.

But that will disappear very quickly. By the time you hit 40 if you’re not walking a very narrow path of good habits, you’re going to feel like crap, you’re not going to feel motivated, you’re going to look like shit.

Start practicing that narrow path of good habits right now, right now when you’re in your early 20s and late teens. It’s very critical.

Guys, leave me a comment below. What do you think? Maybe some of you are older. You can talk about your experiences or maybe some of you are younger, what you’re doing to walk that narrow road of good habits and push yourself developing the good habits early on.

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15 Comments on "20’s vs. 30’s: Picking Up Women"

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10 months 21 days ago
Thanks, man! Dig the website. I’m almost 40 and I agree with you about taking care of your body at all ages but especially as you get older. My romantic path could be summed up as followed: <18 mostly confused, romantically frustrated, 18-22 madly in love and then heart-broken, 25-32 development of player with a heart, 33-39 slightly confused player who wishes he had an awesome woman but more interested in other stuff to spend much time with long-term romance. Difference in pickup/romance at different ages for me: <18 – still learning what is going on/being so shy/falling in love about a girl a week – missed many great opportunities due to shy/"scared" of women/feelings 18-22 -getting over shyness and finding great women/girlfriends but not understanding how to deal with certain situations which then leads to being dumped/heartbreak 22-25 – recovering from heartbreak, dating but not looking for anything serious, still getting over heartbreak. Meeting tons of women through friends and going out. If I had a better attitude at this time, I could have been dating some really awesome hot girls. But it took me a long time to get over heartbreak and to get my self-confidence game back… Read more »
11 months 29 days ago

what if you started the game late? like at ages 25-28, are you screwed as a man? if your a late bloomer, it will be harder to get a young girlfriend that is in her early to mid-20’s? a 20-something woman?

1 year 1 month ago

It would be good to hear a few more of the advantages that men get in their 30s and 40s. One point that is important is that dating in the modern world is an INTERNATIONAL game – just like businesses don’t settle for shitty local suppliers when they can get things made overseas with better quality for less. Dating is EXACTLY the same. Don’t like American women’s entitled attitudes? Just go meet hot Mexican women in your own country – or mix with young international students at your local university, or go abroad to a less developed country and play the mysterious foreign gentleman card. I’ve done all of the above and, honestly, I barely even notice women from my own country these days, they just have no leverage over me any more in the dating game. Obviously being a little older, wiser and with more money helps you to meet different international women.

1 year 1 month ago
Your information great. In your 40ies you do have to walk a tighter walk to stay healthy. The biggest problem I see here in this wonderfull US society is that middle age men that are single who are attracted to younger women get constantly disrespected by everybody. They get disrespected by men there age, younger men, some senior citizen men. They also get disrespected by younger women, middle age women, and senior women. They get disrespected by authority figures such as police officers, FBI’s, governments, media, and judges. If your a older man who is attracted to younger women you are hated in the United States. There a lot of special names older men get called who attracted to younger women such a creep, creepy, and perverted. I have seen ads of singe women who demanding that man does not contact her if her is past a certain age. Our society here in the US accepts that type of behavior from women. Those type of women should be degraded, for disrespecting a man pass a certain age, but they are celebrated. Having to deal with all this bull as a middle age man your supposed to be motivated in meeting… Read more »
1 year 1 month ago

I’ll be 50 in December, and where my age shows up is on my online profiles… in person I look ten years younger because I stay in shape, however the profile is a dead giveaway because it lists my age. BTW, Derek, I finally got those certifications I told you about in 2008 and will be testing for Cisco CCNA on the 28th. I’ve left the concrete industry after 18 years and now do IT support here in New Orleans.

1 year 1 month ago

Answer one thing and one thing only: Have you ever tried on Indian women in India. I am asking because I tried some approaches for 7-8 years and I still have not got 1 single date. If your material works tell me honestly, please dont like to get a measely 1 product sold. Its a matter of far more precious time.

Alfeus Ambambi
1 year 1 month ago

Any girl can contact me

1 year 1 month ago

Great video Jesse. Man i can’t believe how fucking fast time flies, I was around 21 when I first started following you (Mr. Derek Vitalio) and this year I just turned 30!
Luckily I’m still healthy and active (don’t drink or smoke and workout 3x a week), although with a bit of a belly who just doesn’t seem to go away. But I’m afraid what I’ll look like by this time next decade! If the 30’s goes as fast as my 20’s went..damn man..I really wanna enjoy it!

Btw, you said you live in Florida, how can you wear a dress shirt in this fucking Florida heat? I live in Miami and sweat like a pig even wearing shorts and tank tops!

Anyways, keep up with these awesome videos, I’d love to meet you in person someday brother.