4 Mistakes Older Men Make When Pursuing Younger Women

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-By Caleb Jones

Younger women is a topic I haven't discussed here in a while. Bad me. Though I still date women my age (and older!), younger women have become such a normal and regular part of my life, I no longer consider it something unique or interesting enough to talk about. Again, bad me.

Since we're talking about much younger women here, this article is really geared towards men over age 30 or so. If you're much younger than 30 you're welcome to read on if you're curious, since this is something that will be affecting you in a few years.

Instead of talking about what to do to attract and date much younger women, something I've talked about before, today I'll discuss what not to do.


As usual, we need to get our definitions straight. By "much younger women" I'm usually talking about VYW, which I define as women between the age of 18 and 23. There are three types of VYW:
  • Type 1s, VYW who are disgusted at the thought of dating any man older than about four or five years older than they are, regardless of how good-looking or confident the older men might be.
  • Type 2s, VYW who are extremely turned on by much older men, and are usually turned off by, and bored with, men in their own age range.
  • Type 3s, VYW who don't really care about a man's age and don't make a judgment about it one way or the other. However, dating much older men is still often out of their comfort zone, not because they aren't interested, but because they've never done it before.

By "older men" I'm talking about men between the ages of 30 and 49 or so, though men in their 50s who have followed my advice and taken care of themselves physically certainly apply also.

The older man / younger women stuff also generally applies to any man who is hitting up any woman of legal age who is more than 10 years younger than he is. (Since men hitting up women within one to nine years younger is considered "normal" by society in most cases.)  So in a way, a 45 year old man working with a 26 year old woman would apply here, even though she's technically not a VYW.

Here then are the four mistakes men most often make when trying to attract younger women.

Mistake 1: Trying To Act Younger

This is the granddaddy of them all. All the time I'm running into guys who tell me things like "I'm 36, but I look 30, so I tell women I'm 29." Less often, though still regularly, I see guys in their 30s and even 40s who try to dress, act, and talk like men in their 20s. In extreme cases these guys invade the clubs or college campuses to hit on younger women where they often look woefully out of place.

While there are always unusual exceptions to every rule, this approach does not work. It fails for a very simple reason: The VYW most likely to have sex with you are the Type 2s, which are women who like much older men and don't like younger men their own age. Being an older man, but acting like a younger man (or worse, lying about your age) doesn't make any sense. You are destroying the very thing these Type 2s crave.

They don't want a 38 year-old guy who acts like he's 27. They want a 38 year-old guy who acts like a decently cool, non-creepy, 38 year-old guy. That will turn them on. A lot.

Trust me, when you act your age, but are cool and non-creepy, Type 2 VYW are literally the easiest women to have sex with quickly. I've been doing this for years, and to this day I'm still surprised how fast and easy it is (once you find those Type 2s of course).

It's true that if you're really good looking or have extremely strong game you can overcome the fact that you're acting younger and score with those Type 2s anyway, but why create the extra work for yourself? Dumb.

In most cases I've seen, and I've seen a lot, the reason guys try to act younger is because they're trying to have sex with the Type 1s. I've got news for you. If you're over 30, you will never, and I mean never sleep with a Type 1 VYW. Ever. (Unless she's a hooker and you're paying her). Type 1s are horrified at the thought of having sex with men much older than they are. "Ew! It's like fucking my dad! Gross!"

This is not ASD...no technique will bust through this. It's simply a very strong, visceral preference, often based on the age of her parents which obviously you have zero control over. Even if you've think you've had sex with a reluctant Type 1 VYW before, it's not because she was a Type 1...she was a reluctant Type 3. If she was a Type 1 you would have never gotten her pants off.

The good news is that the world is filled with super hot Type 2s and Type 3s, and I'm talking about what most men would consider 9s and 10s. These women will be more than happy to sleep with a much older man. So all this acting younger shit isn't necessary.

I am the exact opposite of these act-younger guys. Whenever I go out on a first date with a VYW, not only do I not act young, but I will often play up the older man aspect. I know that since she's agreed to a date with me, she's not a Type 1, so she's either a Type 2 (in which case fast sex will be very easy as long as I don't majorly screw anything up) or a Type 3 (in which case my odds are a little lower and a little more comfort-building time will be required).

So I dress a little classier, talk a little slower, drop the energy level down just a little, talk more about the wisdom I've learned over the years, and exhibit other older-guy behaviors. In other words, all the things you would never do if you were on a date with an over-33 woman (because then she'll shove you in Make Him Wait zone).

Mistake Number 2: Acting Like A Creepy Older Man, i.e. Being Horny Or Sexual Too Fast

One of the greatest pieces of seduction advice I've ever heard was to "risk creepy". This means that when you're escalating on a woman, you need to push the envelope. Even if you think she might consider what you're doing "creepy", you need to go for it. That doesn't mean you cross the line, but it does mean you are very aggressive, and err on the side of "creepy" rather than "nice guy".

This is very, very good advice, I do this myself, and I recommend it to all men across the board...

...except older guys trying to hit up much younger women. This is the one exception to the rule. If you're older and she's much younger, you need to be non-creepy. If you start talking about how hot her boobs are or tell her how you "can't wait to get her back to your place", she's going to vanish fast, even if she's a Type 2.

Younger women, even Type 2s, are hypersensitive about creepy older men, as well they should be (for their own safety reasons). Instead of being a creepy older guy, you need to be a confident, safe older guy. Focus more on being confident, outcome independent, non-reactive, and classy. If you think a move might be considered creepy, don't do it, especially if you're talking over texts, online, or in a public place, and/or if you have not established clear rapport yet. Even if you have, be careful.

I see way too many older guys who do have chances with younger women completely blow it by being too creepy, too verbally sexual, way too fast.

Mistake Number 3: Not Paying Attention To Personal Appearance

I've already addressed this point before, including in one of the links above, so I'm just going to summarize it here.

Some older guys think they can wing it with their personal appearance and look just like a normal, every day guy just like they did back when they were 25. These guys dress like nerds, have hair and grooming that look like crap, and worse, are often way too skinny or fat.

Back when you were 25, sure. You could dress like crap and not worry about your hair or your clothing too much, and still probably get laid. But if you're 44 years old hitting up 21 year-old women, I'm sorry, but you're going to have to step it up a little. Being fat, or having hair grow out of the side of your neck, or dressing in styles that were outdated 20 years ago might be perfectly okay for provider-hunting women your age, but it won't be okay for the younger ones.

You must take care of your physical appearance more than you did when you were a younger dude. This includes your body and clothing. I've made numerous posts about this lately, so click around this blog and take a look at a few if you have not read them yet.

Now look. This does not mean you need to look like George Clooney. I sure as hell don't, and really didn't back when I was balder and fatter. But it does mean you need to pay attention to your body, grooming, and fashion and place a higher priority on these things if dating much younger women is something you're interested in.

By the way, I think society downplays the awesome superpowers a man has when he's both older and physically attractive. If you're well over age 35 and you're still decent looking, you can pull off some pretty amazing things...things that could never be done by younger men, or men your age who look like typical, dumpy, married beta males.

Good-looking older men really do rule the roost in a very real way. I'm quite serious about this.

Mistake Number 4: Being Limited By Your Own Societal Programming

Some older guys who would really like to date younger women, and be good for them, stop themselves because they have thoughts like...
  • I shouldn't date a woman that young. It's just not right.
  • No woman that young would ever be attracted to a man my age.
  • Everyone will think I'm shallow if I dated a woman that young.
  • A relationship with a woman that young would never work. We're in completely different places in life.

These are all thoughts coming directly from Societal Programming. As such, these thoughts are all bullshit. I shall tackle each one:

I shouldn't date a woman that young. It's just not right.

There is absolutely nothing wrong, immoral, or unethical about dating a much younger woman provided these three things are true:

1. She is of legal age of consent where you both live.

2. The relationship is 100% consensual on her part.

3. You are always 100% honest with her, and are not lying to her or leading her on.

If you're being completely, 100% honest with her, and she's willing, and she's legal, go for it. Date all the younger women you want. There is nothing wrong or evil or immoral about it.

Only when one of those three items above are not true do we start having serious problems. So always check ID, always be honest, always make sure it's consensual, and be rewarded with a clear conscience.

No woman that young would ever be attracted to a man my age.

Ohhhhhh, wrongo! There are millions of younger women out there who are dying for a confident, non-creepy, much older man to sweep them off their feet. It's all over the place, and I'm living proof of this, as are many other older guys in the manosphere.

I estimate that at least 15% of younger women are Type 2s. Trust me, these women have a rough time. They sit in class all day long fantasizing about having sex with their 45 year-old algebra teacher, but they can't tell any of their family or their girlfriends because of the ridicule they'd receive. These gals hope beyond hope that someday they can find a (non-creepy!) much older man to fulfill the fantasies they've had all their lives.

True stat from my life: Just under 50% of all the women I've had sex with since I turned 35 years old were age 18 to 23. I'm almost 42 years old now and this has not let up one bit.

Believe me, those women are out there.

Everyone will think I'm shallow if I dated a woman that young.

Sadly, there is some truth to this one. Many over-33 women are going to be utterly furious at you. Men their age dating younger gals is the biggest threat to these women, and many of them can't emotionally handle it. Other men your age, who are married to old, overweight, nonsexual wives may also be upset. (Gee...I wonder why.)

I have two responses to this. The first one is...so what? Outcome independence. If some forty-something shrew glares at you when you walk down the street with your 20 year-old MLTR, that's her problem, not yours. She's more than welcome to go have sex with a 20 year-old guy, and her forty-something girlfriends will give her high-fives and talk about how independent and liberated she is. So fuck 'em. It's all hypocrisy and bullshit Societal Programming anyway.

The second answer to this is that no one said you need to get serious with these women. If you simply want a younger woman as an occasional FB, go ahead. Getting into a super duper serious relationship with an 18 year-old probably isn't a great idea anyway, be it monogamous or open. So don't over think this stuff. Date younger women in whatever capacity you desire. (Just make sure you don't lie to them or lead them on...remember our three rules above.)

A relationship with a woman that young would never work. We'll be in completely different places in life.

First, remember what I just said. You can date younger women, but you don't have to get super duper serious with them. Keeping things casual with these women is perfectly fine (as long as you're honest with them!). Most women this age aren't wanting super serious relationships anyway. As I've talked about before, when a woman is between the ages of 18 and 23, she considers that play time, not serious time.

That being said, I can tell you from vast experience that "being in different places in life" has absolutely nothing to do with how happy a man and woman will be in a relationship, provided the man and woman are attracted to each other and have compatible personalities. If those two things are covered, the "being in different places in life" doesn't matter at all. Here are a few random examples from my life over the past 7-8 years:

1. The longest consistent relationship I have ever had with a woman outside of my nine-year marriage was an almost five-year relationship with a woman I met when she was 19 that lasted until she was 24. She was a FB for a long time, then I later upgraded her to MLTR.

2. One of the most mentally rewarding relationships I ever had was with a woman I dated for about 2 years, while she was 19 and then 20. She was extremely intelligent and amazingly mature for her age, and we had many long, detailed, philosophical discussions that were the equivalent level of discourse as when I date a woman in her 40s.

3. I have had several MLTRs or FBs who were 20 to 23 years old, who lived in her own homes by themselves, owned her own cars, had their own full-time careers, did not have any kids, and paid 100% of all their own bills with zero help from family, government, or ex's.

While this is certainly not the norm for that age range, there are many women out there like this. I have really been blown away by the quality of many younger women out there. "Younger woman" does not necessarily mean "dumb bimbo".

(And yes, many younger women are the opposite, and are indeed dumb bimbos. Great. Keep those at the FB level. They can be fun too. Some of my most fun FBs were in the young dumb bimbo category. They're wonderful.)

Lastly, don't forget that just because you date younger women does not mean you can't keep dating older women too. I have a woman in my life right now who is 44 years old, and she's friggin' fantastic. Unless you choose to live a monogamous lifestyle (cough! puke!), you can date women of all ages, younger and older, and probably should. No reason to limit yourself to one or the other.

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