What’s Possible for Older Men with Younger Women

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The following is an except from my book The Ultimate Younger Woman Manual that I have expanded for the purposes of this article.   One of the more common questions I’m asked is, “I’m a really old guy. I’m X years old. Is it reasonable for me to expect to date/have sex with a hot 22 year–old? Or should I just forget about learning game or relationship techniques and just pay for sex?” 

-By Caleb Jones

It’s a valid question. After teaching thousands of men these techniques over the last ten years, the age categories of men break down into something like this:  Men in their teens or twenties are younger men, not older men, so they don’t require any special changes in their approach with younger women. The advantage younger men have with younger women is, obviously, they don’t have to overcome the discomfort and negative Societal Programming regarding a large age difference.

The disadvantages younger men have are:  1. They usually have very little money, thus making them less attractive to females (and as the West continues its slow collapse, this will become a much bigger problem as time goes on).

2. They are extremely outcome dependent. Another unattractive trait. 

3. They tend to be short-tempered, quick to anger, and put up with a lot of bullshit drama from women. 

It is those aspects that actually help older men attract much younger women. But regardless, younger men don’t have to engage in any special type of dating techniques in order to score with younger women. Men age 30-34 are also not what I consider “older men,” and these days, by and large, most younger women don’t either. As I’ve discussed on this blog before, men in the modern era are much more immature at older ages these days. Thus, most men age 30-34 look and act like younger guys. Because of this, they also usually don’t need to do anything radically different for VYW, though some adjustments might be required depending on the circumstance. 

Men age 35-39 are indeed “older men.” Once you cross over age 35, younger women are definitely going to place you into that “older” category. The good news about men this age is that while they are considered “older,” they are often still youthful in appearance. I personally consider age 37 as the age where a man peaks in physical attractiveness, and some of my own informal polling in my real life and on the internet seems to indicate many men and women agree with this. 

Men in their forties are still able to date younger women of any age, but the difficultly level is increased dramatically, and personal appearance becomes much, much more of a factor. Younger men can look like bums or dorks and still get to sex with younger women. Older men can not. Strangely, the older you get, the more important it is to keep up your physical appearance (if your objective is to date younger women, that is).   It’s important to do literally everything right when in your forties when dating much younger women, since the margin for error is razor thin.  Sugar daddy game, a game style where men find women on sugar daddy dating sites and either pay women for sex or imply they will pay, is an option for men in their forties, but it’s not required. I’ve dated VYW while in my forties without paying them any money with zero problems and I know many other men in their forties who do the same. But again, you have to do everything right, success rates/response rates drop to tiny percentages, and you really, really need to put in the numbers.

Men in their fifties break down into two subcategories. The first category, by far the smaller of the two, are men over 50 who are still reasonably physically fit (not like Schwarzenegger in his prime, but reasonably fit for a guy in his fifties), have decent skin, have a (reasonably) full head of hair (or a completely shaved head) and know how to dress well. If that’s you, then in terms of women, you’re essentially a man in his forties, so what I said above regarding men in their forties more or less applies to you.  
The other type of guy in his fifties, a much more common type, is the typical fifties beta male who has let his physical health and appearance go after decades of monogamy or neglect. He’s either chubby with a big pot belly, or way too skinny with no muscle to speak of. He’s also balding, has poor skin and/or teeth, slovenly grooming, dresses like a dork, has weak, stooped body language, and has an overall beta male demeanor. He looks like the typical “dad.” Not a good look.  If that sounds like you, you must focus very hard on your physical appearance, and set a goal to maximize your appearance as much as humanly possible, even if it costs money and time to do so, which it probably will. Confidence, fitness, fashion, and grooming should be addressed heavily before you spend a lot of time going out to attempt to date much younger women (unless all you want to do is pay hookers). 

While you’re improving your appearance, I don’t recommend you focus completely on VYW, since dating them at this point will be a challenge. Instead, you can temporarily focus on dating women within your own age range or focus on dating women much younger than you but not quite as young as VYW (women in their thirties, for example), or focus instead on sugar daddy game where some money is involved. I generally advise men over 50 who are still in appearance optimization mode to avoid normal (non-sugar daddy) game with VYW until they get their appearance under control.  I personally know several men in their fifties who are dating women in their mid-twenties, without paying for it, with no problems, but these are men who take the time (and money) to take extra care of their appearance and health, far beyond the typical Western beta male 50+ dad or grandpa. 

Men in their sixties or beyond should either focus on sugar daddy game if they want VYW (which should not be a problem financially for you, since by the time you’re in your sixties you should have plenty of disposable income) or, if they optimize their appearance, focus on younger women in their thirties or forties. Non-sugar daddy game with VYW for men over age sixty isn’t really an option unless the scenario is highly unusual. If a woman as young as 22 is willing to have sex with a man over the age of sixty for no exchange in money or gifts, even if he’s reasonably attractive for 60+ man, she will at least expect some kind of payment, gifts, or support at some point in the interaction soon. Again, yes, I realize there are odd exceptions, but those are exactly what they are: exceptions. 

This should not surprise nor bother anyone. When I’m well over age sixty I fully expect to have to shell out some money, at least to some degree, if I want to get funky with a woman in her twenties. As I said above, this shouldn’t be a problem because by the time you’re over sixty, money should not be a problem for you, and you should have plenty of it. Read this article here where I clearly state that every man over age 50 should have a net worth of at least one million dollars anyway, and sixty is a full ten years past that. (The comments from a few enraged Millennials in that article are a fun read too. I highly recommend you go take a look.) 

If you plan on only dating women within plus or minus ten years of your age for the rest of your life, that’s fine, and you’ll never need to worry about any of this younger woman stuff. But if you plan on getting sexual with much younger women either now or when you get much older, now is the time to plan and prepare for this so you won’t have problems later in life when getting to sex with younger and more attractive women becomes more difficult.  Remember, Alpha Male 2.0 is a long-term lifestyle design plan. Living a great life in your thirties while letting everything go to shit in your fifties or sixties is not smart, nor is it a life path you want to follow. 

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