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.

“Love is a Concept Invented by Poor People…” Seeking Arrangement Founder, Brandon Wade


“By encouraging people to find and negotiate an arrangement, we hope to create modern relationships based on open-mindedness, open communication, brutal honesty and transparent expectations.”

“This is the future of dating.” BW


Ashley reminds me of someone I once dated, also an entrepreneur.


Now understand something here: The woman posing with Mr. Wade in the above photo would have no problem waltzing right over his dead body if he weren’t filthy rich.

I don’t mean this in any negative way, but Mr. Wade had to make himself valuable in order to earn visibility, which everyone understands and appreciates.

This revelation set him ablaze with passion to acquire the one asset that would act as a carbon credit for whatever he lacked elsewhere.

Next thing you know, he goes meteoric and declares “love is a concept created by the poor!” before heading off to CNN for an interview.

By the way, a rough translation of his statement is If you don’t have money, no one will love you, which is why poor people created it in the first place. 

Okay. Whatever. I get it. We get it. Pretty much all of us, really.

Baby Boomers like myself suffer physical attrition after enough water’s under the bridge.

Fortunately, though, many of us are able to leverage money and power against the cost of aging and manage to stay square with the gods.

Now you know why seekingarrangement.com claims 1.9 million subscribers…and climbing.

On a general note, there is absolutely nothing novel about prostitution.

Whether you couch it as “Hey, I just need a little help with college,” or “Hey, want a blowjob?” you’re still hooking.

Having said this, everything these days is relative.

Just how relative depends on the price tag.

The more you spend, the more normal everything seems.

On a related note, most of the women my peers end up with are passed from one older man to the next within their own immediate peer group.

This is because the women in question are known commodities who’ve been properly vetted, and therefore, predictable within reason.

The downside is that there is often a limited supply of such women within certain demographics, which usually triggers bidding wars resulting in some of the best television fodder on the planet.


So, You Want a Daddy?

perfect-woman-clockwI’m cracking myself up this morning.

No seriously.

For all you unemployed millennial’s out there, hope’s on the horizon.

You don’t have to earn a PhD. – or even a GED.

But you will need other assets worth bartering.

I should be charging a consultation fee for this, but you caught me on a good day.

The Most Common Gold-Digger Backstory

Teenage daughter works as a part-time waitress. She lives in a trailer with her biological mother and unemployed stepfather, whose on disability over an alleged lumberyard mishap.

In the mother’s mind…

“The disability payments ain’t worth shit money-wise, but that daughter of mine has an ass…if she only knew how to use it right. I ain’t talkin’ flat-out hookin,’ but maybe goin’ in to the big city and learnin’ how to talk right for god’s sake. Get rid of that gum chewin,’ act like she belongs, ya know…find out where the money’s at…”

This is the template from which most gold-diggers are hatched and bred. It’s as old as the hills, the situation I mean…and how to get out of it.

But there’s a lot more to it than what you read, so I’ll help fill in the blanks.

While finding a “daddy” sounds like a cakewalk to many of you who think that youth and beauty are enough to seal the deal, think again. Cultural evolution is no different than biological evolution, except that it’s a thousand times faster. So while the gold-digger of old was easy to pull from a police line-up, today’s incarnation is virtually unrecognizable even under polygraph analysis and near lethal doses of sodium pentothal.

With this as a backdrop, here are 25 clues from my own personal experience tells me you’re someone I don’t want to know.

1] Gum chewing.

 2] Ending sentences with prepositions. While sometimes it’s okay to end sentences with prepositions, you best know when it’s okay. Otherwise, stick to the rules.

Incorrect usage: Where is he at?

Correct usage: Where is he?

.3] Improperly conjugating verbs

Incorrect usage: “She run off.”

Correct usage: “She ran off.”

4] Mispronouncing words that reasonably educated women learn by the time they’re 6.

Example #1: Never say expresso. The correct word is Espresso.

Example#2: It’s also not Excetera. It’s et cetera.

5] Me vs I

Incorrect usage: Jim and me are going to the beach.

Correct usage: Jim and I are going to the beach.

6] Gone vs Went

Incorrect usage: I should’ve went somewhere!

Correct usage: I went to the store. I should have gone to the open market instead.

7] Could of vs Could have

Incorrect usage: I wonder if I could of majored in English.

Correct usage: I wonder if I could have majored in English.

8] Cheap handbag. Only acceptable if you just picked up something interesting at a vintage shop.

9] Don’t overuse foundation. It makes you look like you’re hiding something. Ask any stripper.

10] Know the difference between sexy and sleazy. It’s part self-confidence, part self-actualization, and part breeding.

11] Bad posture is a clear and present sign of a mother who doesn’t know better.

12] If you’ve never heard of Shakespeare, you’re toast…even if your target is an engineer who only reads blueprints.

13] Money is not the determinant of class. Class is the determinant of class. Then money is the determinant of class.

14] If you can’t walk in heels, learn at home.

15] If you’ve never attended college and you’re not a famous entertainer or entrepreneur, lie.

16] Never trip out at the sight of an expensive home or car. It’s just a home and a car.

17] Never ask a man you don’t know for money or he will have sex with you without paying for it.

18] Hit on anyone other than your date and it will be your last.

19] One online profile is enough. More than one with entirely different information is identity theft.

20] Have interests outside of going out. Some people enjoy reading books, for example.

21] Using country vernacular is fine as long as people know you know the difference between ignorance and the Queen’s English.

22] Never name-drop unless your own name is worth dropping.

23] Your cell phone is simply a cellphone, not a codependent relationship.

24] Repeat after me: “I have a good relationship with my father.”

25] When referring to family members, never say “grampah and grammah.” Instead, say “grandfather and grandmother.” This also applies to mother and father, whom can be also be referred to as simply “mom and dad.”

I could go on…

Baby Boomer Suicide Rate Rising [as funds for concubines dries up]



The recent Great Recession was hard on almost everyone, but especially baby boomers [generation born between 1946-1964] who had decades of savings to invest.

Side note: Money is supposed to fill in all the existential angst after life exacts its pound of flesh and leaves us with less physical relevance. 

Thus, it’s no surprise that a rising number of middle-aged people of that generation resorted to suicide as the weight of economic problems overwhelmed them.

Since that time baby boomers have had the highest rate of suicide of any age group in the United States, which is interesting given the fact that people between the ages of 40 and 64 have historically had one of the lowest rates.

Add to this conundrum the fact that baby boomers are now sliding head long into the over-65 demographic, which is ground zero for historically high suicide rates.

Put another way, if you don’t have money at this writing, you’re pretty much screwed.

According to the article, since the beginning of the Great Recession, 8.8 million jobs were lost, according to the Bureau of Labor Statistics.

Middle-aged people were disproportionately affected in terms of lost property value, household finances, and lost retirement savings.

Twenty-seven percent of those aged 50 to 64 experienced reduction in salaries, higher than any other age group.

On a related note, of those baby boomers who committed suicide from 2005 to 2010, 81 percent had prior mental health or substance abuse problems.

Although suicides for baby boomers could level out as the economy improves, experts say the fact this generation is entering older age is worrisome.

So now even if you have money, you’re too old to really enjoy it.

The key is not to let things get to a point of escalation. When people are suicidal, they’re rigid and not thinking clearly.

Dr. Jill Harkavy-Friedman, American Foundation for Suicide Prevention says, “The key is not to let things get to a point of escalation. When people are suicidal, they’re rigid and not thinking clearly.”

But she is wrong. They are thinking very clearly, which is the problem.

How do you talk an 80-year-old man without money out of hanging himself?

It doesn’t make sense. The man is thinking quite rationally, in my view. What’s the point of going on if you’re broke, and, for all intents and purposes, broken physically?

Is there any hope?

Not really.

From personal experience, I can give you 10 things older men [those over 65] can do to dramatically improve their mental health –– but we’re talking about older men who don’t have to worry about their next meal.

For such men, hope is everywhere because they can afford it.

More specifically, here are 10 ways to insure that it sticks around a long time:

1] Hit the gym on a daily basis, interact with people, and reduce stress. Exercise releases endorphins, which create feelings of happiness and euphoria without heroin. It also boosts self-esteem by providing a sense of physical relevance and self-possession that other older men lose along the way.

2] Check your testosterone levels. At this stage of the game “normal” levels probably aren’t enough. So boost them. Even if it leads to premature death, what the hell difference does it make is all you’re doing is dying in slow motion?

3] Be sexually active. If you’re bored with your wife, figure out how not to be bored with her. If she’s not interested, hire a surrogate wife. Many women I know provide “girlfriend experiences” with a full rate schedule they keep on Ipads. Many keep them in their gym bags. And for God’s sake, get a scrip for ED medication if you think you need it. Most 25-year-olds are using it, so why not you?

 4] Don’t shy away from cosmetic improvements. If your teeth look like crap, fix them. If your jaws are hanging like liver from the sides of your face…facelift! Then there are fillers, micro-dermabrasion…I could go on. Just do it.

5] If you drive a Buick la Sabre, I can’t help you. 



6] Do something you’ve always wanted to do, but for whatever reason haven’t. Nobody’s going to care if you decide to go back-packing in Yosemite after spending 40 years behind a desk. 

 7] When was the last time you went clothes shopping? Seriously. Most older men look old because they dress like people who should already be dead. Thus, I suggest you let your “girlfriend” decide what to buy. Pink pleated pants and golfing shirts are now customary attire for the dead at wakes, fyi.

8] Spend time around younger people whenever possible. It has been demonstrated time and time again that people become conditioned to their surroundings, which should not include graveyards and hospitals.

9] Stop talking about your aches and pains, and for God’s sake avoid the obituaries. Nobody wants to hear about your aging joints because only old people have aching joints no matter how ridiculous this sounds. And talking about the death of anyone but, for example, an otherwise youthful and healthy downhill skier is a buzzkill.  

10] If you take yourself way too seriously and can’t remember the last time you laughed, you’re like the guy with the Buick.

I’ll give you 10 more in upcoming blogs…

“Lyin’ Eyes” Reinterpreted

Don Henley was 28 when he and 27-year-old Glenn Frey wrote Lyin’Eyes.

The year was 1975.

The story goes that they were in their favorite LA restaurant/bar Dan Tana’s where they watched beautiful young women hitting on rich, older married men and decided to write about it.

From the vantage point of men in their 20’s, I can certainly understand their passionate disdain, as they felt entitled to the attention by virtue of youth alone.

Nonetheless, fast-forward to today’s urban world and I will comment on each verse from the perspective of an older man:


City girls just seem to find out early
How to open doors with just a smile
A rich old man
And she won’t have to worry
She’ll dress up all in lace and go in style


City girls know exactly what they doing, which is why many of them are among the 1% without so much as a G.E.D., or discernible profession. 

Late at night a big old house gets lonely
I guess every form of refuge has its price
And it breaks her heart to think her love is only
Given to a man with hands as cold as ice


I have yet to meet a gold-digger who was unhappy in a 10 million dollar home. Not one. Furthermore, most don’t care what’s in a John’s heart, or even that he has one, as long as she gets to travel. Put another way, it’s a symbiotic relationship.

So she tells him she must go out for the evening
To comfort an old friend who’s feelin’ down
But he knows where she’s goin’ as she’s leavin’
She is headed for the cheatin’ side of town


Most gold-diggers cheat. So what? As long as the John doesn’t find out what difference does it make? She’s still faithful to the arrangement.

You can’t hide your lyin’ eyes
And your smile is a thin disguise
I thought by now you’d realize
There ain’t no way to hide your lyin eyes


Most men I know set specific parameters like anyone running a successful enterprise. Applicants sign employment contracts and live within the parameters. 

On the other side of town a boy is waiting
With fiery eyes and dreams no one could steal
She drives on through the night anticipating
‘Cause he makes her feel the way she used to feel


There will always be a boy somewhere waiting for pretty much anyone, anytime. It’s obviously not enough, so she parses.

She rushes to his arms; they fall together
She whispers that it’s only for awhile
She swears that soon she’ll be comin’ back forever
She pulls away and leaves him with a smile


Unless he figures out how to make a bundle, he’ll only be a fleeting screw. Of course, most young guys who make a fortune when they’re young tend to go through women like water, so now who’s crying?

She gets up and pours herself a strong one,
And stares out at the stars up in the sky.
Another night, it’s gonna be a long one.
She draws the shade and hangs her head to cry.


This is the funniest thing I have ever read. Her head is sitting in a $20,000 french armchair with a glass of champagne. Nice try, though. 

She wonders how it ever got this crazy.
She thinks about a boy she knew in school.
Did she get tired or did she just get lazy?
She’s so far gone she feels just like a fool.


Lazy? Are you insane? Women like this work their butt’s off to live like this. What? You think money just falls from trees?

My oh my, you sure know how to arrange things.
You set it up so well, so carefully.
Ain’t it funny how your new life didn’t change things?
You’re still the same old girl you used to be.


Most insightful verse in the song. I’ve never known a gold-digger to change his or her stripes. 

As young men, even they could see that people are what they do.

How Gold-Diggers Parse Love


The following account is real.

I bring this to you not because it news, but because it’s not:



Did you ever really love me?


Honestly, the first year of our relationship I was very much in love with you. We traveled all over the world, stayed in beautiful hotels, dined at great restaurants. It was wonderful. Then your business went downhill and we stopped doing things.


We stopped traveling but we still did things. 


What things? We mostly stayed at home and watched movies.


So you were in love with the lifestyle.


You were the lifestyle.


Understand that many men are simply incapable of falling in love with any woman who doesn’t satisfy an exacting set of physical standards.

The problem is that gold-diggers have those standards etched into the fabric of their DNA, so they hold all the cards.

And people wonder why so many affluent older men become trapped in vicious cycles of defeated expectations, as they try to get “perfect” women to love them for who they are.

In my world, fortunes come and go every day, mostly under these circumstances.

Aging is a weird thing. We learn more about a lot of things, but the basics never change: love, lust, money, but in the reverse order.


Cash-Strapped Russian Sugar Daddies Running Back to Their Wives

31BC326700000578-3471744-Strike_a_pose_Maria_pictured_urges_women_not_to_fall_in_love_wit-a-126_1456876617119It’s not just Russia.

Gold-Diggers state-side are on life support.


I have no further comments to make about this other than to just enjoy reading all about something you already know to be true…kind of like therapy.


Jerry Hall, 59 Engaged to Rupert Murdock, 84



Needless to say, this story is not really about Jerry Hall and Rupert Murdock.

It’s about age differences, and how money and power are balanced against relative youth and relative beauty on a very public stage.

What’s obvious is that Hall stands to inherit a massive sum when he dies, which, from an actuarial perspective, is just around the corner.

So she gives up a few years of her life in exchange for vast riches, while he gets to sleep with a younger woman with whom he shares common interests and lifestyles.

In this sense they both win.

But is this it?

Is it just a business decision?

Does Murdock think he’s being used? Probably not.

Does she love him in the way most people think of love?

I don’t know and neither does anyone else.

What I have found through personal experience that most older women – of which Hall is certainly a member – are far less interested in sex and romance than they are companionship.

There are exceptions, but not many.

The “Old Man” and the Motorcycle

Memorial-Day3-580x464Nothing quite says midlife crisis like the Harley Davidson Motorcycle, right?

Another day, another stereotype.

I’m accused of being in the midst of one for many reasons, not least of which being that I have a young girlfriend.

1] It’s all about money.

2] He’s intimidated by women his own age.

3] He’s a narcissist who can stomach his own reflection.

yada yada …

It never ends.

Not to bury the lead, I don’t own a motorcycle – but I find it interesting on many levels.

For one thing, I like it’s group nature. It’s an activity – and for many, lifestyle – that people of all socioeconomic backgrounds can share.

And it’s also damn manly in the traditional sense most men think of it. Think Steve McQueen in The Great Escape.

I think of it as an antidote to the PC virus.

I’m also drawn to the sense of adventure, hanging out with a bunch of guys who, after decades of work, family and Little league, are finally able to bond once again over beer and broads.

It’s an adult rite of passage where the holy “hog” unlocks the key to death with dignity for all, the penultimate send-off into oblivion, finger in the wind at the Devil’s Crossroads.

Come on, tell me you’re not intrigued.

One last shot at youthful defiance.

Don’t tell me you don’t watch those old Zeppelin videos on YouTube in the dead of night.

A 2010 market study by J. D. Power & Associates discovered that the average motorcyclist in the United States is a man who is about 50 years old, and Forbes Magazine confirms that the “sweet spot” for motorcycle buyers is the mid 40s to the early 50s. The problem is especially acute for Harley Davidson, as the 109 year-old company has a customer base that is almost as old as it is. It may just be an urban legend that Harley handlebars are now designed to comfortably support a beer belly during a ride, but it makes sense, given the fact that most older men [not to mention younger men] are out of shape.

Nonetheless, “Google” searches turn up ad after ad of sexily clad young women and handsome, fit young men to fuel the fantasies of middle-aged guys. Motorcycle manufacturers lure older buyers with a promise of a return to their youth and vitality: Male bystanders watch with a mixture of respect and envy, as the women of the town are smitten by the eye candy rolling into town. The riders wink at the ladies and act like the masters of all that they beheld, since they could now afford the luxury of motoring slowly through town.

Yea, and everything else in the universe is also reduced to a cultural stereotype.

My point in all of this is, WHO CARES?

If a guy wants to ride a motorcycle after spending his life chasing the dollar let him have his 2nd Summer.

I agree that Harley’ are loud and obnoxious. So is my stereo system.

Getting older is a drag, folks. We’re gonna act out.

This is because there’s not a damn thing we can do about universal absolutes, so we will absolutely, positively garnish the journey to make the ride smoother.

I might add that many guys ride for charities, raising lots of money for good causes. Others just for the hell of it. So what?

These guys are tough enough to deflect your punchlines, ageist stereotypes, and general ridicule.

Time Magazine in June of 2014, wrote “It’s bike night at the Harley-Davidson Museum near downtown Milwaukee . . . bike night in Milwaukee sure looks like Old White Guy’s Night.”

Green with envy.


Life is supposed to have a beginning, a middle and an end. The same ones, usually.

But for many, myself included, the story arcs are backwards.

Dennis Quaid at 61


Dennis Quaid is 6’0″, #175 at what looks to be well below 10% body fat.

By comparison, I’m 6’1″, #230 at 13% body fat, which places me in the top 1% of my age group.

Most people consider this extraordinarily fit.

But I’m not shredded like a slab of turkey jerky, and herein lies the rub.

See, in order to put on – and hold – lean muscle mass at less then 10% body fat [at age 61!], you’ll need help of the preternatural kind.

To wit, Quaid has more lean, angular mass on his shoulders and arms than any man his age can normally produce without “help.”

I’m not accusing him of steroid use because I don’t know him. Maybe he’s a genetic freak. I’ve seen a few in my day.

For everyone else, pulling off tons of lean mass with low body fat is impossible without tinkering with testosterone levels.

What? You think we’re immortal?

Since when do men our age look like Quaid?

Some of you may consider him too lean, too small…kind of ragged, wasted even.

But for men who want this look, it can be acquired at “wellness” clinics and individual physicians operating throughout the United States.


1] If you want to perform at levels similar to what you achieved at age 30, you will need a lot more than hard work coupled with a hope and a prayer. 

2] I’m not judging, just exposing the truth.

3] You have to decide if the consequences of steroid use are worth the risks.

4] Denial is the mother of delusion.

5] I don’t care how Dennis Quaid chooses to live his life. His job is to entertain, not inspire.

Just trying to keep it real around here.