Dating Women of Different Ages

Different age groups of women are dated differently and managed differently in relationships. If you don’t understand the differences between these age groups, you’re going to have a lot of problems in your woman life. In this article, I’m going to show you exactly how to calibrate your dating and your relationship management for the age of the women in your life.

It’s really important to remember that when you have a date with a woman who is 19, that should be managed differently than a date with a woman who is 39 or 47. Not all ages of women are the same. There are radical differences; some are good and some are bad. Likewise, there are pros and cons to younger women and pros and cons to older women. It’s just false to say that one group is great and the other is terrible. Take it from a guy like me—I’ve been with many women of all ages in the past, both sexually and in long-term relationships.

Age 18-23

This is the age range I call “Slutty Disney.” That’s the age at which ASD is lowest but Disney desires are very high. It’s a strange age. Women this age are wild, free, happy, dramatic, and irresponsible. One of the challenges of dating younger women is that they are extremely irresponsible in terms of time management; they’ll cancel dates and forget meets, and they have lots of chaos in their lives, but their ASD is much lower. 

ASD means “anti-slut defense,” which is that voice inside a woman’s head that tells them they “shouldn’t” have sex with you (even if they want to) because they don’t want to be a slut.

ASD is at an all-time low at this age, and it’s not unusual to see women this age have sex with five, 10, or even more guys in a six-month period. A lot of women under the age of 23 go through a slutty phase. Over a period of a few months, they have sex with a bunch of guys, and then suddenly say, “Oh my God, I’m a slut! I shouldn’t have done that.” So they back way off and they never do that again. Talk to a lot of women in the thirties and forties, and they’ll tell you they did the same thing when they were younger.

It’s not a problem for them, and it’s not a problem until after they get out of the slutty phase. Even so, if you want to have sex with her 22-year-old friend and it’s a non-monogamous relationship, she’ll probably be cool with it. Will she be perfectly cool with it at age 37? That’s a no.

Next, they get into monogamous relationships and promptly cheat. I have said many times that women under the age of 23 are functionally incapable of monogamy. Yes, I understand there are exceptions. To be fair, if a guy is that age, he is probably cheating too. The takeaway from that is that when you date a woman under the age of 23 in the context of a serious relationship, even if it’s monogamous, get ready to be cheated on. Women this age don’t do monogamy even if they say they do.

Despite all the sexuality, a woman’s Disney fantasies are at extreme levels at this age. All she can think about is falling in romantic love, getting married (or the equivalent) with her Prince Charming, and having babies. But let me update this a little bit: That was true when I first wrote it nine years ago. Women that age are not only very horny and have low ASD, but they also have strong Disney desires. This has changed a little, though; society has moved in a certain direction. The entire Western world moves to a cultural and political left a little more every year. Today, you have a lot of women in this age group who don’t necessarily want to get traditionally monogamously married and don’t want kids.

What hasn’t changed is their desire to move in with a guy; they still want to do that as soon as they fall in love. Then they might say they don’t want to get legally married or they don’t want to have kids; it’s kind of a cool thing for Gen Z women of this age to say they don’t want kids. These women are lying; if you check back in on them in 10-15 years, they’ll have a kid or two. Biology trumps all this shit as usual.

Not surprisingly, women at this age make the most irresponsible decisions—having a baby with the wrong guy; marrying the wrong guy; moving in with the wrong guy; all these things are very common at this age. They are constantly jumping in and out of relationships. Women’s biological default isn’t monogamy—it’s serial monogamy. Back when I originally wrote about this, you could simply watch how often they changed their Facebook relationship statuses. These days, Facebook isn’t a big thing for women of this age, but back then, I had women who were FBs and MLTRs who would literally get a new boyfriend every six to eight months.

Women this age are extremely drama-prone, but—and this is a big “but”—in the face of a strong, confident man, they will happily divert their drama to places besides him. This diversion is usually impossible with older women, who tend to feel like they have the right to throw drama at their man if they’re in a bad mood. This is a key difference that many men don’t understand between younger and older women. It’s not that any one group has more drama; it’s that you can divert the drama from younger women and/or “train” (for lack of a better word) them to not give you the drama. If it’s an older woman, she won’t buy into that shit. If she’s mad at you, she’ll give you the drama because that’s what she wants.

So it doesn’t mean you don’t have drama with younger women. It just means that younger women are more likely to throw drama in other directions.

Women this age use alcohol and drugs in insane amounts, far more than any other age group, regardless of whether they’re over 21 or not. This is absolutely true, and that has not changed. It’s yet another testament to society’s insistence on maintaining laws that don’t work.

At this age, a woman is all about fun. The god of having fun trumps everything else in her life until she gets to about the age of 24 or so. If it’s not fun, she’s not interested. When you’re talking to women of this age online, you want to play up the fun factor, especially you older guys going after much younger women.

Ages 24-26

This is the group I call Miss Independent. At this age, women back off on the promiscuity a little—I said “a little.” Instead of having sex with five or 10 guys, she’ll tone it down to two guys, and she’ll happily rotate new guys in and out all the time. I’m amazed at the number of women in this age group who are having sex with exactly two guys pretty much at all times. That could mean she’s playing the field or cheating on a boyfriend—it doesn’t matter what the context is. It’s a magic number for them, just enough to have fun and get laid, but not enough to violate any of the slowly building ASD. Yes, as a woman slowly ages, her ASD slowly rises. Women this age have a little more ASD than women in the previous age group.

They still drink and party a lot, but they won’t drink to the point where they’re puking all the time. They still love drugs and alcohol, but they’ve learned more about their own bodies and have moderated things a little. There are exceptions to everything; I’m generalizing here. Keep that in mind.

The defining attribute of women in this age range used to be how they tended to avoid boyfriends. They didn’t want to be tied down, even to the ones who follow their orders and kiss their asses. This is less true now than it was when I originally wrote about this back in 2011. I’ve noticed now that women of this age are more likely to get a boyfriend than they were 10 years ago, but they don’t have this attitude of immediately attaching themselves to a boyfriend the way they did when they were 18 or so.

They’ve learned in their 18-23 years that boyfriends are trouble. They lie, cheat, get jealous, get needy, hurt their feelings, and leave them. So fuck that. They still love men, fun, and sex. She’s still going to play the field, enjoy herself, and be independent. It’s women in this age group who will literally lecture you after sex about how they don’t want anything serious and how you are not their boyfriend. This is the exact opposite of women in their thirties; we’ll talk about that in a minute.

Ages 27-29

I call this category “Oh my God, I’m still single.”

Women in this age group are identical to the 24-26 crowd except that now the biological clock has begun ticking. They love fun and being independent, especially now, since they’re making money for the first time in their lives. Women in their twenties make more money than men in their twenties. Really, the late twenties are when women really start making real money, and that gives them a sense of confidence and power they didn’t historically have at that age.

But they are now getting concerned that a) they haven’t found their soulmate yet; b) they don’t have any babies yet (assuming they don’t). It’s not like she’s a heat-seeking semen missile like some women in their mid-thirties, but she starts feeling this biological or sociological need to get married and have kids. A childless woman who hits age 28 will suddenly feel the need to have kids even if she doesn’t know why. It’s the most amazing thing, and I’ve seen it many times. They’re fine for the longest time, and then they hit about age 28, and suddenly they want a baby.

Really watch the birth control if you’re playing around with a 28- or 29-year-old who hasn’t had any babies yet. Yes, you dumb asses, too many of you guys are having sex with random chicks without using condoms. These women will cast off their no-boyfriends rule and start carefully looking for a boyfriend/husband/provider, but they won’t leap into anything, and they’ll keep looking until one comes along—no more than one or two guys at a time because their ASD is slowly rising.

Women this age tend to have the most sexual hang-ups and issues and they’re the hardest to make come by far. If you want to make them orgasm (and you always should), do some tongue exercises, do some finger stretches, and be ready to put in the work. Get a good vibrator, too. It solves a lot of problems.

Ages 30-32

I called this “ASD Blossom.”

At this point, the ASD in her brain is at full bore. The need to find a husband/provider is an important mission in her life. It is at this age that women are the pickiest about the men they date since that’s when high ASD meets with the fact that she’s still young enough to still be pretty and in-demand. Let me update this a little bit, though. That’s not quite as true today as it was 10 years ago. Women today who are 30 still look really damn hot. At this age, you really can’t tell whether they’re 30 or still in their twenties. Because of that, a lot of women in this age group are still acting like women in their twenties. So what I wrote back then isn’t necessarily as accurate today as it was back then.

Previously, thanks to the blossoming ASD for the first time in her life, she would go without sex if she didn’t meet any men who are up to her provider/hunting standards—but this isn’t really true anymore of women in this age group. It is true once women hit about 33. Which brings us to…

Age 33-38

This category is called “I’m a Lady Now.”

Age 33 is when everything changes for a woman. It represents a magical line they cross, and all of a sudden, their attitudes about dating, men, and sex completely change.

At this age, a woman has gone through all kinds of failed relationships, divorces, cheating boyfriends, horrible first dates, and asshole male bosses. Men are no longer fun. Rather, men have become the enemy, or at least a necessary evil. She likely has a job she hates, bills she can barely pay, and possibly kids that stress her out. On top of all this, she sees all kinds of wrinkles when she looks in the mirror along with cellulite and saggy boobs, and that just pisses her off even more. Modern-day single women in their thirties are big walking balls of stress.

The worst decade of a woman’s life in the modern era is her thirties. It’s the most stressed out and pissed off she’ll ever be. Women in their twenties are having a great time; women in their forties are more or less settled. Women in their thirties are not a happy group.

Things like enjoying herself, being happy, and achieving goals are all gone; they’re silly things she liked when she was younger. She has responsibilities now. She can’t just go around having sex and having fun when she’s got bills to pay and kids to take care of. It’s time to buckle down and slog through the pain and drama that is life. You’ll see this with online dating profiles: “I’ve had my fun. I’m done having sex and having fun. I need a goddamn boyfriend (or husband) right now. I’m done with the fun.”

What a horrible place to be in life when you’re “done having fun.” I’m almost 50 and I’m nowhere near done having fun.

She’s a lady now—she doesn’t “do that” anymore. Yes, she used to fuck guys on the first or second date, but that was then. She’s a lady now. If you’re on a date with her and trying to have sex, you are in for a treat! She’ll immediately whip out a 300-page book called “Dating Rules and Regulations.” This is the kind of shit you’re going to get from women at this age. Yes, there are exceptions, but the exception proves the rule.

If she’s actually strong enough to overcome the rivers of ASD flowing in her system, you’re going to have to commit to being her full-on, loving, monogamous, ass-kissing boyfriend—or no sex. Remember, she’s a lady now, and ladies don’t have sex outside of deep, meaningful, committed relationships. The exception to this rule is if you’re an ex-lover of hers or a reasonably good-looking, younger-looking guy who effectively presents himself as sexual but with absolutely zero provider potential, which is something very difficult for most men to do, even those with solid game. 

What I really mean by this was men their age. If you’re a younger guy, you can go after women over 33 and you won’t run into a lot of these problems; these problems apply to men in their thirties or forties, who will get thrown into this category with women because they have provider potential. But if a woman is 37 and you’re 22 and you have good cougar game, you could get laid pretty quickly. She can fuck you and rationalize it because you’re not actually dating, so it’s OK. Her mature age has increased her ASD but has not diminished her chick logic.

Ages 39-49

I call this group “Delusional Empress.” Get ready!

Essentially, this is just like a woman in her thirties, but times two. Single women in their forties, especially those who are not yet overweight and have retained some good looks, tend to think they are the most beautiful, intelligent, desirable, strong females in the universe. She’s a catch, and you’d better treat her that way. All other women are silly and immature.

Usually, men wanting to have sex with them are expected to treat them like queens well beforehand. Gold-digger behaviors and expectations are at their height at this age range.

The most gold-diggers I’ve encountered have been women in their forties. You’d expect gold-diggers to be these sugar-baby types in their twenties, and those exist too, but mostly they’re women in their forties, at least prior to sugar daddy game becoming a more common thing in society.

Men who don’t treat them like goddesses are somewhere between “not gentlemen” and “pigs.” That remains true today. Men who reject them are “shallow” or “clearly have issues” and should have taken the time to understand how amazing she is, all while having no sex and paying for dinners and everything else. The painful irony of all this is that women at this stage are really horny. I’m serious. The problem is that due to massive amounts of societal programming, ASD, and raw arrogance, the only way they can have sex is with a man who attracts them does what he’s told, and commits right up front.

So if she likes a guy but he doesn’t behave exactly the way she expects him to behave, she gets very upset. She needs to get laid, dammit, and you need to do what you’re told!

Yes, I’ve had women in their forties who are FBs or MLTRs, and they’re monster horny. You need to come over right now and fuck them—and if you can’t for any reason, they get really mad. The only women I’ve had get angry with me because I couldn’t go over and have sex with them are women in their forties. They have a high degree of horniness and a high degree of ASD, which is not a good mix, unfortunately.

I feel sorry for women in their forties, frankly. To be clear, I am super attracted to women in their forties, thirties, and twenties. I’m not one of these guys who believes they suddenly stop being attractive when they hit 30. Women in their forties are super hot, as long as they don’t get overweight. So this isn’t a reflection of how I feel about women in their forties.

The slightly good news is that if you manage to bed one of these women, she will crave your cock like you’ve never seen. You’ll get texts every day to get your ass over to her place so she can cram your cock inside her again. I’m not exaggerating. Yes, there are exceptions, and I’m not talking about married women in their forties. I’m talking about women in the dating pool who are single and don’t have live-in boyfriends. This is as true today as it was when I originally wrote it.

Age 50+

I call this age group “Realization.”

Previously, by the age of 50, women had largely lost their ability to use their looks to get whatever they want from men. That has radically changed since I originally talked about this. We now have women in their early fifties who look fucking hot. I don’t mean “hot for 50,” I mean hot.

And as time goes on, that age is going to keep rising. Soon, in our society, you’re going to have women in their sixties who actually look hot. It’s going to happen. We’re not there yet, but there are plenty of women in their fifties who look damn good.

Women this age finally realize there is no knight in shining armor who is “out there somewhere.” They finally realize that because they can’t flip their hair and stick out their chests to get what they want from men anymore, men are either super boring or completely incapable of adhering to their Disney fantasy life plan. She finally understands that there is no third category of “perfect guy.”

I wrote a big article years ago called “The Myth of the Submissive Alpha Male,” which is the submissive fantasy unicorn man that women have in their minds of this strong, kick-ass alpha male who takes charge and doesn’t take any shit… who takes out the trash, hands over his money, and does exactly what she says to do. There’s no such thing.

Most women this age are married to either low-end beta providers who bore the shit out of them (but who they can’t divorce because she’s too old to snag a new man) or a cheating alpha she can’t stand but reluctantly tolerates and still can’t divorce. Both of these are true of women in their fifties. I’ve seen a lot of this from women in their fifties who know their “market value” isn’t high enough to snag another man, so they just put up with what they’ve got. In both cases, she accepts that “this is how men are.” Yes, it takes 50+ years, but they finally figure it out.

The single ones grab pretty much whomever they can and live out the rest of their lives with drastically reduced expectations from their husbands and men in general. This acceptance of reality and lack of sexual power is why women over 50 tend to have lower divorce rates. However, and I’ve mentioned this before in articles, the number-one growth age range of divorce spiking is people in their fifties. The divorce rate in this age range has quadrupled since the year 2000. Why is that? As I said, more women in their fifties are starting to look pretty damn good. So unlike 30 or 40 years ago, women in their fifties don’t look like old ladies anymore. And they know they can divorce the guy they’re with and get another one.

For some women, this is a great weight off their shoulders and many women have a reawakening in their fifties, and they achieve the peace and happiness they’ve always thought they wanted. I’ve met a lot of women this age who are really chill and relaxed, and I would venture to guess that the happiest decade for women in modern society is their fifties. Their twenties are fun; even though they’re kind of chaotic, it’s pretty fun; their thirties are a nightmare for women; their forties are tough for women (although perhaps not as bad as their thirties); but in their fifties, women kind of relax. I think most women in this age range have a less-bad time than women of other ages.

Calibrating Based on Age

Your ladies will increase and become easier if you calibrate your approach to each woman you meet based on her age range. Is she 19? Play up the fun aspect. Is she 26? Make it clear you’re not needy and aren’t looking for a girlfriend. Is she 35? Hit the gym, get buff, dress inexpensively, throw a strong sexual frame at her and ask her to pay for the date, since you “don’t have any money.” Or you can dress really nicely, talk about your last promotion, kiss her ass all over the place, and be prepared to commit. Those are the two categories of men for women in their thirties.

You get the point. The bottom line is to never assume that all women of all ages are seduced the same way. There are significant differences. Many times I’ve talked about how I will never again cold-approach new women over the age of 33, online or in person, but that is no longer true. I’ve changed that since then, but the standard model I’ve taught for many years is that if your primary objective is to get to sex as quickly as possible, you really want to draw a line at the age of 33 and only date women under that age. I understand older guys may not want to do that, but that is kind of a universal maxim.

Based on these descriptions, you can see why. Closing on these women is completely doable but requires a different mindset.

It’s important that you understand these age ranges and age differences. There is a school of thought among some guys that insists that women are women and all women want the same things. No—women of different age ranges and cultures behave differently when it comes to their sexual lives, relationship lives, dating lives, and marital lives. Be aware of this; it’s an important topic to get wired into your head.