Anorexia the Height of Achievement to Women of Means [and the go-to look for the affluent older men in their lives]

3a44935300000578-3955356-critics_say_celebrities_like_alexa_chung_33_-a-52_1479682994594Alexa Chung, 34.

At my health club, there is a certain go-to look among the women of affluence: “Long, lean, timeless and elegant” is the way its described.

Bulky, curvy and/or overly muscled women are considered low class.

It’s a look relegated to strippers, sugar babies, and prostitutes for the most part.

But it can also include tattoo artists, bartenders, figure models, and “convention” girls hired to showcase things like expensive automobiles.

Thus, an incredibly thin body has become the new way to signal wealth and distinguish oneself from the masses.

“I’m successful, intelligent and at the top of my game…”


Alexa Chung Amal Clooney look so under-developed that, in some cases, critics say they appear pre-pubescent.

Some stars appear to have waists the same sizes as catwalk models, many of whom measure 24in — the same as an eight-year-old child.


Achieving this look suggests an abundance of leisure time, which is also important element in this equation, reinforcing the overall narrative.

One must spend hours honing their physiques at the gym, and “the income to maintain a fantastically expensive diet and exercise regime.”

Of course, pressure from outside sources as well as from their own personal relationships play a part.
Many affluent older men I happen to know personally prefer this look in their women.

They see it as intelligent, sophisticated and timeless…kind of the way they see themselves.

The women, therefore, are reflections of their narcissistic projection.

A businessman wants to introduce a Stepford Wife to his colleagues because of what it conveys.

After all, no one could possibly suggest that she didn’t care about her appearance, or that she was unhappy at home…or depressed.

In fact, quite the opposite.

When a man introduces a woman who is curvy or in any way carrying extra baggage, the take-away is that he is less successful, less powerful.

Further to this is simple physics.

Smaller women are also easier to control in bed, thus reinforcing the man’s power and influence. As men age, they are less agile, which emaciation on the part of the partner mitigates.

And finally, there is the “pre-pubescent” thing.

I hate to dwell here, but in my view, many of these men secretly harbor a fetish for little girls. It’s kind of like statutory rape, only legal.

Seriously, why else would grown men prefer sleeping with someone who resembles a 12-year-old child?

Gotta’ Love Mickey Rourke


Baby Boomer, Mickey Rourke, 64, struts his crazy shit in Beverly Hills like nobody’s business.


Look at this guy: 64-year-old amalgamation of physical strength and gender-bender audacity.

He’s irony in motion, annihilator of boundaries, the Louis Vitton and Pomeranian standing guard at the castle gates.

After a certain point in life, successful artists just don’t give a crap what you think.

They care about what they think, which inspires the rest of humanity question conformity in general.

So while most guys his age [and level of success] don’t look anything like Mickey Rourke, inside we’re all very similar: Driven, defiant, audacious, struggling to keep the pool of relevance deep and vast against what seems like endless odds.

For this alone you have to give credit where it’s due. Mickey Rourke has taunted fate, living his life inside out in all its glory.

His appearance is emblematic.

Whatever his deepest motives if there are any], the man lives life with a middle finger to the wind, and for that he deserves respect.

Fame, Power, Money and SEX in Entertainment


Newsflash: It’s not just Fox, and it’s not just entertainment, but mostly entertainment because people who choose this route are most often dealing with some form of psychiatric disability.

This aside, when I was a budding young actor in NYC [and before i chose photography and writing], this kind of thing was commonplace.

If you wanted something, you have to surrender something – usually your dignity.

I mean, come on! You weren’t just asking for a job as a bagger at Whole Foods for god’s sake.

You wanted fame and fortune and everything that goes with it.

That was then.

The great thing about being older is that you can look back at all the shit you had to swallow to get ahead and know that no one will ever pull that shit on you again, not least of which because you’re no longer a hot 22-year-old model with your hands out.

Psychology and the Retirement Nest Egg

heart-moneyMost of us Baby Boomers have launched retirement calculators a thousand times. Almost every financial institution has one, and invariably, the ones we tend to go to offer the most optimistic outlooks on how much we can spend until the day we die.

The problem is that no one knows exactly when they’re going to die, or if they’re going to die for those of us who’ve opted for cryogenic sleep.

Nonetheless, there is still an annual charge for keeping a body on ice, perhaps for a thousand years or more, so there’s that.

So here’s the dirty rotten obnoxious and existential nightmare-provoking truth: You probably won’t outlive your money.

As I stated in my book, Urban Dystrophy, The Perverse Truths About Mid Life in the Big City, a starter portfolio is $5,000,000.

I know I know. How the hell are you supposed to save $5,000,000 on a $500,000 annual salary over the course of 25 or 30 years?

After taxes somewhere in the 39% range, you’re only taking home somewhere in the $300,000 range.

If you own a home that costs $1,000,000, you can expect to pay $25,000 in property taxes and after a 20% deposit, approximately $60,000/year on a mortgage.

Now add electricity and other related home expenses and you’re down to $200,000 — and you haven’t taken a vacation, bought a single meal or paid a single car note.

Back out those expenses and with luck you have approximately $150,000 left over.

If, however, you have 2 kids, you have basically nothing left over.

So, for the past 25 years you’ve made $12,500,000 and don’t have a dime left in the bank.

Even if you were frugal enough to contribute $75,000,000 a year to a retirement account [for 25 years], you would still only have $1,875,000 in contributions, plus investment interest at an average of around 5%, so $2,800,000 – $3,000,000.


If you retire at age 65, that’s not even close to enough for anyone I know.

The reason for this is because you want to live the same way you did before you retired, which means you’ll need a few million more to generate the income you need to avoid running out of money before your time is up.

For most men I know who give a crap about living well in retirement, the number is around $7,000,000.

At a 5% return, you’re still at 350k/year.

If, however, market crashes, feel free to put a bullet in your head because being broke isn’t worth the struggle for older people.


Most men my age validate themselves based upon their relative financial security.

And while every psychiatrist on the planet will call bullshit on this because it’s about as unhealthy a perspective as one might have given the vagaries of money.

But nothing is going to change it unless you plan to join a monastic congregation in Burma.

Money is kind of like a living thing that follows you around wherever you go.

When it doesn’t, you have a big fat fucking problem.

Walk into a car dealership, new prospective home…or hell, the Apple store, and see what happens when the money monster isn’t with you and smiling.

Then you know true meaning of nausea.

The reason you feel the hubris of filthy rich older men with the tans, snow white veneers and $3000 suits is because they’ve beaten the system.

They’ve overcome whatever life can throw at them, shy of a brain aneurysm, stroke or stage 3 cancer.

In other words, they can ride out the highs and low of the stock market, or pay marginal tax increases and still live their lives without making any changes whatsoever.

This is where you want to be, but unfortunately, probably won’t be.

The media is always talking about wealth; who has this or that.

Magazines feature $5,000,000 homes like they’re normal abodes for anyone who’s led a reasonably successful life.

But this is a lie.

The only way to afford a home like that is to inherit it or sell something.

Salaries don’t pay for homes in that price rage.

Investment capital does.

Psychologically, this is a massive hurdle for otherwise success older men facing retirement.

You look down the road at the rest of your life and you don’t see the picture you’ve been sold…and there isn’t a damn thing you can do about it.

Many men lose their younger girlfriends and/or wives to cut backs in lifestyle.

The ones who don’t tend to be with women their own age who have little to no value on the dating market, who and just sty put.

On top of all this we have a government hell bent and determined to tax out of existence everyone in the middle to upper middle class – including the bottom end of the top 3%.

This is because there are more of them than there are people with $100,000,000 or more who don’t feel any tax increases whatsoever.

So now we have an oligarchy and you’re on the wrong side of it.


1] Figure out how much you absolutely, positively need to live the way you want to live and carve your expectations accordingly.

2] Accept that fact that as you near the end of your life, your retirement savings will be nearing the ends of it’s life.

3] Add 5 years to your anticipated lifeline and then hope and pray you don’t outlive it.

4] Find someone in your personal life who can handle stock market turbulence.

5] Don’t marry a gold-digger unless you’re in the $100,000,000 demographic.

Mick Jagger, 72, Fathers 8th Child Melanie Hamrick, 29

243DF49600000578-2884903-image-m-48_1419344998898Melanie Hamrick, 29, is mother to Jagger’s 8th child.

BTW, who cares if it’s his 22nd child? He could father a nation and still support them so shut the hell up.

As for the rest of you, try having just one you can afford.

The rest of us are sick of paying your bills.

4 Nannies + 2 Twins = How Money Evens the Playing Field


Rolling Stones guitarist Ronnie Wood, 69, and his wife Sally, 38, tend to their newborns, Gracie Jane and Alice Rose.


In days gone by [lots of them], a man of 69 was, for the most part, on his death bed.

The very last thing he was doing was having children with a woman 30 years his junior.

Then something happened [a lot, actually], and this same man is now clean and sober [for the most part, I assume], propped up by the miracles of medical science, and thus, living like there’s no tomorrow.

This is what fame and fortune [fame + money = relevance] does for most men.

It’s like a blood transfusion that just keeps giving and giving.

You’ll note that many of the comments under the article are dismissive of him and his “relationship.”

People simply can’t resist the temptation to criticize his motives, and hers.

Nothing is real. It’s all one big endless past time for a man who has nothing left to do with the time he’s not touring.

Well let’s get real.

No one in their right mind has kids at 69 without the ability to afford nannies…lots of them.

It’s not that he doesn’t want to be a part of their lives, just not all of it.

As for his young wife, she’ll do her part, with lots of help, while her husband does what he does when he wants to do it, because like he’s Ronnie Wood and the scales have to balance somewhere.

Wealthy older men have reached a point in their lives where they just don’t give a crap what other people think about them and their lifestyles.

For one thing, they don’t have to. Nothing rides on their reputations in the office.

This is the beauty of success. No one can fault you for it no matter how you choose to live out your years.

It’s like a golden wrapper, a force field that follows you around wherever you go.

You walk into a restaurant, hotel, resort property – even local liquor store – and there’s a kind of parting of the waves.

It’s something you get used to, which is one reason men who find themselves suddenly without it blow their brains out.

The story here is really about what it’s like to feel validated for everything you ever dreamed of as a little boy.

For young men there is tremendous pressure to amount to something, to achieve.

And as we age we gauge our success by those around us, hoping that we’re still close to the front of the line, relevant, valid.

All older men validate themselves on their achievements whether they admit it or not.

They subconsciously sum up everything to a series of equations and derive a number that determines their relative worth.

And while some men do not base their lives solely on financial success, I don’t know any.

While vicariously living through one’s children is a fallback position, it really sucks to rely on their financial support.

The moral of this story is that life is a food chain no matter how you dice it.

You have to fight for every scrap, and then live to tell a very tall tale that you and people around you can easily quantify.

It is unforgiving, savage, and brutally objective.

This is why reality television focusing on the super rich is so popular, while anxiety disorders are the most common mental illness in the U.S., affecting 40 million adults…and counting.

Now you know why people beat up on Ronny Wood…and why Daily Mail published it in the first place.

Concluding Remarks and Data Points

  • 1% (2 out of 233) became wealthy before the age of 40
  • 3% (6 out of 233) became wealthy between age 40 and 55
  • 16% (38 out of 233) became wealthy between age 46 and 50
  • 28% (66 out of 233) became wealthy between age 51 and 55
  • 31% (73 out of 233) became wealthy between age 56 and 60
  • 21% (48 out of 233) became wealthy after the age of 60

So yes, Ronnie was one lucky SOB.

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.

Inter-Generational Relationships Are Challenging Like All Other Relationships […with a few exceptions]


So let’s say you’re an attractive 30-year-old woman who’s fallen for a man of 60.

While it may provide shelter from the storm of corporate climbing and adolescent pack animals, it’s not all roses.

There are inherent risks, difficulties, and pitfalls that may prove impossible to overcome.

But most women I know who find themselves in such relationships know exactly what they’re getting themselves into, and won’t leave without a severance package or SWAT standoff.

Generational Divide

An older man may find himself in the position of surrogate parent if the younger woman is substantially younger, or the man is more traditional and/or less fluid in his approach to life.

If, for example, he spent his entire career surrounded by corporate types, adhering to stodgy cultural norms, his ability to communicate with a creative Millennial, for example, may prove impossible.

On the other hand, if he’s lead guitarist for a major rock group or an A-list actor, she’ll assume the role of surrogate parent.

Strong, Powerful Men Didn’t Get to Where They Are by Accident

Older men may have mellowed somewhat with age and maturity, but this mild-mannered guy is only a cover for a ruthless and aggressive nature that got them to where they are in life. In other words, the nice house didn’t happen without a fight.

This usually means that as long as everything is going well, you get the cool older guy. But the moment the shit hits the skids, you get a first hand look at human predation from the perspective of prey. Men will defend and protect their financial interests and prosperity over all else in their lives, including you.

Of course, gorillas do the same damn thing, so it’s not exactly news.

Taming and Older Man is a Ludicrous Pursuit

Why women like to fix older men is beyond me. I can understand trying to get a 25-year-old guy to get out of bed in the mornings, and to get a life. But older men have been there, and at this stage of the game don’t give a shit what anyone thinks about their lifestyle habits.

He’s already self-sufficient. He doesn’t need you to pave the way forward. You can’t cut him off from his friends, or interests, or in any way undermine his life. It’s already worked for him. His entire psychological framework is built around decades of experience. Give it up.

If You’re Seeing a Married Man, Love Isn’t Enough to Shake the Tree

The married guys I know with “women-on-the-side” like the no-strings-attached erotic sex, even the fantasy that love plays a major role in all of it. But understand that it’s still fantasy. All of it. Your best bet is to find a recently divorced older man of affluence, or just go the married route in exchange for college tuition and be done with it. Graduate programs run 50k. Get real.

The Sexual Equation

No matter how successful and older man is he cannot reverse the aging process. Understand that as you turn a year older he turns 7 years older [after a certain point in life]. So if you want to build a long-lasting relationship with him, you better make damn sure your sexual rhythms and desires are on the same page.

While adventure and passion are still very much on the table, things will eventually change.

Of course, it’s also important to keep in mind that a young man will eventually get bored with you, especially after he’s achieved success in his 40’s, and will often replace you with someone half your age that he won’t be bored with. It’s a cycle that tends to repeat itself a few go-rounds in life.

Parental Issues

In my case, the woman in my life’s parents refused to speak to me for the first 3 years of our relationships, assuming that I was buying her love, and at the same time, stealing her youth and opportunity.

Thankfully, it passed and we now have a wonderful relationship. But it was awkward. Be prepared for that.

Completely Different Entertainment Preferences

In many cases, taste in music is a major marker of significant age differences. In my own relationship, though, our tastes were identical.  In fact, she had more Zeppelin albums than I did. Another ironic twist of fate was that I was the one going out every night of the week, while she preferred evenings at home watching TV, painting or video editing.

I could argue that she made me grow up, and that all had to do was provide financial stability, love and commitment in exchange for a more adult lifestyle. It was a small price to pay, and probably paid for itself given my wayward leanings.


Affluent older men do NOT choose women unless they’re prostitutes. It’s the other way around. This is one of life’s biggest misconceptions about the older man/younger woman paradigm.

This being the case, she will decide whether or not she can handle the difference in age, the disparity between their respective success and power, his intransigence, the sex and whether or not he knows – or gives a crap about – Taylor Swift.



“All Middle-Aged Men Want To Be Thought Of As Cool…”


This statement is thrown around a lot these days, mostly by older women who are sick to death of older men acting like juvenile delinquents.

But I can assure you, I know just as many 40-60-something women who make them look like choir boys.


Okay, enough with the stereotyping.

It’s boring, mostly because it’s true.

Older men who can afford to “act out” [when I was a kid, they called it “acting up”], do so because they can.

And because they can, they do. Not all, but those who can afford the fallout.

This is how many gold-diggers spot their marks, by the way.

Anyone who can afford to stand out does so for reasons that have pretty much everything to do with the fact that they can do so with impunity.

The same is true of divorced older women who go on jaunts to Cancun with their single – and married – girlfriends only to come back knocked up by teenagers at beach raves.

Understand that, from an actuarial point of view, there is nothing ahead that remotely resembles “I’m getting hotter,” or “Aging is an abstraction.”

It’s in your face and it’s mouth is wide open.

What better to do than go back to a time before all the existential crap laid its wicked hands on you and stick it to time, even if you’re still sticking it to yourself.

Affluent older men [and women] do, in fact, buy sports cars and motorcycles, drug themselves silly, engage in risky sexual encounters, do stupid shit like jump out of airplanes, climb mountains and play with gold-diggers as though they were domesticated animals.

It happens to all of us at some point along the way, when time is slipping so fast you start with the opiates to slow the shit down.

Not to bury the lead here, but it’s obvious by now that both genders play the same game.

Perhaps it could be argued that for men aging is a tougher pill to swallow.

The hunter/predator/drone paradigm only works when the joints are nimble and quick to react.

But women who take on traditionally male roles suffer similar fates as time beats down the doors, wreaking havoc on once vibrant skin, teeth hair, nails and everything else for that matter.

Neither gender fares particularly well where the body is concerned.

The bottom line is this:

Older women want men  – within their age demographic – to kick the older man/younger woman habit so they can have a fair shot at settling down with one of them.

And while there are ample studies that suggest older women are just fine being alone or in the company of friends, it is only so when faced with the alternative of an average older man.

This is why we see so many of them revisiting adolescence on Spring Break before finding themselves empty, depressed and alone.

See, men are superficial enough to keep this thing going until the day they die.

Women, on the other hand, can only keep it going long enough to prove a point before moving to Florida, joining a book club, and outliving men by 10 years.

Revenge at last.

[Depending on your point of view].

“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 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.