Why Rich Older Guys Can’t Find the “Right” Women


The reasons men of means have difficulty finding true love has everything to do with them, and nothing whatsoever to do with the relative health of their investment portfolios.


The following is a conversation between yours truly and one of these men.

By the time you’re half way through it, you’ll understand the dilemma.

“John” is a nom de plume.


“I just met this woman who is perfect! Perfect body, nice skin, teeth…and she has a perfect ass. A little flat on top, but I can fix that.”


“Where did you meet her?


At a really nice steakhouse. She was at the bar having drinks with a girlfriend.


Is she from here?


I think so. She’s in school.


How old is she?




So she’s getting a graduate degree or something?


I don’t know all of that, but she is really into fitness and wants to workout with me at the club.


I’m sure she does. What does she do for a living? Does she have a job?


Yea, she’s in medical sales or something like that. She’s really smart.


I bet.


So this is how it all starts.

There’s a checklist that runs in the blood.

You’ll notice the same list in 22-year-old men who don’t have resources and children that must withstand their poor life choices.

Such men can ebb and flow with the tides, relatively unscathed.

But when an older man of means gets caught up in what feels like a rip current, it can drag his entire life straight to hell before he has time to repair the damage.

The point is older men of means have a tendency to forget their age and financial station relative to the women they choose to date.

In their minds, they’re still at Stanford, and the women are on a field in front of them carrying lacrosse rackets.

This is the delusion that settles in like virus and hides out in their spinal columns for the duration of their lives.

It’s incurable, but it can be contained.

Unfortunately, containing it is akin to death to many, so it just does what the hell it wants until there’s nothing left to do.

I can’t tell an older man that his choices are ass-backwards. He doesn’t want to hear it.

What he wants to hear is that a beautiful young woman of unknown origin and lifestyle will love him for who he is.

He wants it to all the be same way things were 30 years ago.

This is the psychopathology.

This is also why these men rarely – if ever – find the “right” women.

They don’t exist anymore than the person they were 30 years ago exists.

Now they’re standing at a steakhouse bar in the middle of a massive metropolis, hallucinating.

And who takes advantage of their hallucinations?

You guessed it.

5 Bullet Points of Note

1] Never choose a woman based solely upon her appearance thinking you can fix the rest of it. In her mind, the rest is not broken. You are.

2] If a woman in a steakhouse says she’s in school at 33, she is in class where you’re standing.

3] Your fantasies are public knowledge, which means that the women you meet have your number.

4] Line items are fine, but not particularly practical.

5] Imagine your world without money and then place that template over the women in your sights.