In teaching friends to “connect” with younger, beautiful women I encountered the attitudes that there is something just not right about a 50 year old man picking up and enjoying the company of a much younger woman. They accepted that the women entered these relationships willingly but usually disparaged the girls’ motives. “Those young women are with him for his money” or travel or car, or some other variation which shifts the focus to a thing rather than the cool man behind it. Their objections were fragile and quickly broke down under any sort of analysis (i.e., you can and should date the woman without bringing money into the issue by doing very cool, but not excessively expensive things), but were initially powerful, emotional barriers to considering the issue. I believe they were propagandized into accepting less than what they deserved, and I aim to correct that.

As to objections we start with the cultural. In American and other Western societies (except Italy and Brazil, it would seem), the church, state, and Oprah Winfrey’s viewership have persuaded us that it is a man’s duty to tie himself to one woman of approximately his own age. If this occurs by virtue of a long and successful marriage then I am all in favor of it: two 80-year olds, still active and “into” each other, have to be a beautiful thing.

The rub occurs with a single man, 50-60 years old. Our society abhors the thought that he might find comfort and enjoyment in the arms [or bed] of a 20 year old girl because this essentially relegates women his own age to ancillary roles. When older women, 50 years and up, are forced to compete with 23 year old HB10+s, it is clear these older women will rarely if ever prevail and their lifelong strategies are thereby constrained.

Society cannot tolerate this age-based unfairness! So it defines the relationship of older men, younger women as “immature” or “unethical.” (It is also terrifying to women that the remaining best strategy, as I hinted above, is to take care of their first husband and not divorce him; make their first one count and they have exploited their one advantage over the younger women: the “Home Court Advantage.”)

When a single 50-60 year old man becomes known, he is often “set up” on dates. Do you know who he is set up with? Most often fat, old women of his own age and with little or no resources or professional skills to bring to the relationship. Her sole qualification is that “they look good together” to outsiders, and that “they’ll each have someone to grow old with.” Never mind that she is sexually unsatisfying to him or reduces his quality of life. And never mind that several or perhaps even most of the women that he is set up with claim to be his age but in actuality are 10 years older. (Isn’t that a pretty picture!) It is as though our society demands that every healthy, successful man has an obligation to identify one parasitic female—that is, she brings little to the equation except taking herself off the rolls of old, single women—and agree to split his assets and time with her whether she is deserving or not.

The amazing thing is that American men are so propagandized, starting in our childhood by our mothers and continuing on with unrelenting fury throughout our entire lives, that they embrace this “duty” as an ethical one.

How many men do you know that divorced, met a woman approximately their own age (through friends) shortly thereafter, and then seemed hurriedly “rushed to the altar” for a replacement marriage?

My belief is that all men should identify what they want in life and then go after it. If women your same age appeal to you, then do it! But if younger women appeal to you, then apologize to no one for who you are or what you want in life and let your chase begin!

This belief is expressed in another way when women (and Hollywood movie writers) say that all men should “date within their league”—whatever THAT means. But when we hear the objection that “that woman is out of your league,” we understand that society is telling us “you do not fit our societal model of who should be dating whom,” because if this rend in the universe is allowed then there will be no men left for the old, parasitic females who comprise Oprah Winfrey’s viewership. My view is: ALL WOMEN ARE IN YOUR LEAGUE. More important, there is NO WOMAN that is “out of your league.”

Riding on the coattails of that cultural assumption is the belief by many older men that young women will have no interest in them. Nonsense! The game is different but the joy open for you to discover is that younger women are dying to find a cool older guy. You know things the young guys don’t. And it isn’t about lavishing money or travel or high living on them; it’s about having a better emotional and sexual life for their time with you.

I recall having dinner with workmates, where a pretty 21 year old girl was desperately trying to gain the attention of a 55 year old guy. She tried everything, even down to unbuttoning the top two buttons of her top, then leaning forward (so he could examine her tits) while twisting and contorting her body so as to appear to be checking the door “for a friend” when her real purpose was to give him permission to look “while she was conspicuously looking away.” He still didn’t take the bait and look … and finally she left, frustrated and crestfallen, for the ladies room.

I asked my buddy, “Are you interested in her?” and he answered, “No, she’s too young for me.”

If by that he had meant, “She is so young that she does not appeal to me” then I would have agreed. It is his right to determine what appeals to him and what I think or desire is of no matter. He should never be out to conform to my expectations, as a high school boy might subject himself to peer pressure. A four hundred pound Pacific Islander girl? If she’s okay by him then I approve, too, not that my approval matters.

But what he meant was, “I believe that she thinks that I am too old for her, as she has already commented that her father is nearly 10 years younger than I am.” When I heard that I was dispirited. He had raised the barrier “She’s out of my league.” Nothing I could say in the time allowed could convince him otherwise. She went home, upset and lonely to her bed and he went home, ignorant and deprived of her wonderful company because of his having unwittingly embraced that detestable cultural rule that all men should date within their own league. (Whatever that means.)

Ignore what others say. If young women appeal to you, and if you’re willing to put in the time and effort to gain the skill of dating and enjoying them, then JUST DO IT. The world will be a better place for it, and your life will improve as well.

Note: my reference herein to “20 year old women” and the like is not meant to impose a preference on my male readers, but to set a lower boundary that the reader should feel free to raise in his own mind as he reviews this memo. Substitute “30 year old” or “40 year old” as the expression if that makes this memo more understandable to you, but be aware that young, beautiful women have no problem developing an interest in men as old as their grandfathers, so long as that man practices “good game.”

And by the way, even 20 year old women are not the lower limit since I have had interested 18 year old women approach, open, and game me. The simple rule is that if the girl is age-legal, you can be 78 years old with a healthy, strong game, and get her attracted and sexually pursuing you … and To Hell with the opinions of those lesser mortals in Life’s bleachers!

Age appropriateness has even made its way into Wikipedia. Note the pseudo- scientific tone of these experts:

A suggestion: read the article then celebrate by picking up, entrancing, and fucking the brains out of a gorgeous, intelligent, sensitive, sweet 22 year old woman—and make her your girlfriend, so long as she promises to be a good girl for you.


I have been fortunate enough to have been able to present a lot of great material in the cliff’s list newsletters and now on the website that have made a significant difference in many guy’s lives.

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