The Inter-Generational Dating Equation [and make no mistake…it is an equation of both heart and common sense]

irrational_man2From the movie, “Irrational Man”

I have cited an article from “Mother Jones,” but I did found something worthy of mention in the context of the older man/younger woman meme.

What happens when you get older is that people expect more from you in the way of cash. It’s how most guys validate themselves after time has taken it’s pound of flesh and what’s left is an investment portfolio.

With this in mind, younger women who date older men usually do so for the lifestyle.

This is not to say that they don’t appreciate the other qualities [i.e., maturity, experience, appreciation, etc…], but without the security, we’re pretty stuck dating women who look like they walked off the set of an arthritis commercial.

There are exceptions, of course, but not many.

Just run the actuarial numbers and this will start to make sense.

Anyway, I have an acquaintance who dates a much younger woman.

He pays her a set stipend each week in exchange for a girlfriend experience.

But guys who front-load like this are on thin ice.

They guide their decisions by the old bird in the hand mantra as if the bird in question weren’t a Tyrannosaur in drag.

The only way to avoid inevitable catastrophe is to let the relationship evolve over time, to stop pretending that your “girlfriend experience” is just a transaction.

This is because, after a while, it starts to feel real – to you, not her.

That’s the rub.

It’s fine to help someone out after you’ve gotten to know them well and trust their intentions.

But NEVER, EVER use your imagination when dealing with someone of motive.

As for the dollar bills in question, it’s been my experience that such men pay anywhere from $6000-$8000/ month – up to about $300,000/year for services rendered – at which point they usually marry with a golden parachute built into the pre-nup.

Is it prostitution?

Yes, of course it is.

My friends usually pay their women in cash and receive sexual favors in return.

But it’s also what’s referred to as a functional relationship by today’s standards among the older moneyed class.

The abnormal and maladjusted ones fall in love and live happily ever after, but I digress.

Successful Older Men Don’t “Choose” Younger Women


As covered in my new release, Urban Dystrophy [@Amazon], older men don’t point a finger and “choose” who they date, unless the woman in question is a prostitute with a voracious pimp.

There are no guns to anyone’s head,  no coercion, no blackmail…and more often than not, no voodoo.

There are simply two people standing in the same space with motives of their own.

But no matter what those motives happen to be, women call the shots. Period. End of discussion.

The last time I felt deceived into believing that I called the shots was back in my 20’s, fueled by piss, vinegar and testosterone in equal measure.

Since that time, things have changed…for the better, frankly.

To say the very least, I’m happy not to be a woman in her 50’s scouring the earth for Prince Charming.

With this in mind, author Renee Fisher recently penned a tongue-in-cheek article titled, “Why Older Men Should Date Younger Women.”

In it she posits 10 reasons why such paradigms “work.”

I will list them and follow with a reality-as-I-know-it discussion.

While I don’t have academic credentials working with people involved in age gap relationships, I have at least 3 doctorates in practical experience.

Before I start, allow me to offer some perspective on where Ms. Fisher is coming from…

She begins with “Women over the age of 50 have been complaining ever since their 50th birthday parties that men their age prefer younger women.”

This is what’s referred to as a set-up, as in you’re being set up to see things from a certain perspective, especially if you’re a female Baby Boomer who’s dating experiences mirror hers.

So here goes:

1. Younger women are universally hot and want sex all the time, except when they are reminding you to take your meds, cooking you great meals or sitting with you in front of the TV, watching all your favorite sports teams in action.

COMMENTS: While it is true that young women are universally hot, it has been my experience that sex happens at the same frequency it does in age-relevant relationships. I might also add that i am usually the one reminding the younger women in my life to take their meds, to learn how to cook, and to seek counseling for texting addiction. Nothing’s a panacea. 

2. Younger women can explain all of the latest music, social media trends and technology to you in a way you can completely understand and appreciate.

COMMENTS: My girlfriend is a computer geek, and while I’m fluent in most geek-speak, getting her to explain something is like pulling teeth from a dragon.

3. Younger women would prefer to be in bed by 9 P.M., rather than going out to a trendy club.

COMMENTS: In spite of the obvious satire here, the younger women I’ve known are into health and fitness and enjoy evenings in front of computers, not bartenders.

4. Younger women take a sincere interest in learning everything they can about the ’50s and ’60s and ’70s.

COMMENTS: Why would I care whether or not someone took an interest in my generation’s formative years? All I have to do is keep an eye on my classic rock collection before it ends up in someone else’s classic rock collection.

5. Younger women love to give massages (while they are naked), apply medicinal salves and ointments to you (while they are naked), and are masters at cleaning your ears and cutting your hair (while they are naked)

COMMENTS: The only women of any age I know who do this are paid in cash.

6. Younger women are attracted to men who are paying alimony and/or child support.

COMMENTS: Younger women are attracted to men who can afford to pay their bills, all of them.

7. Younger women become easily aroused by nose and ear hair and reruns of “Gilligan’s Island.”

COMMENTS: Like women of all ages, grooming is something everyone expects to the same degree, and the last I checked, my girlfriend and I watch the same television shows. 

8. Younger women know all the latest clothing styles, but prefer men who wear shorts, black socks and Crocs.

COMMENTS: At this writing my entire wardrobe consists of John Varvatos, Vince and Prada. 

9. Younger women are universally hot and stay that way, no matter what.

COMMENTS: By the time I’m 80, my girlfriend will still be incredibly hot. So yes, she’s spot-on here. 

10. The most compelling reason for the older man/younger woman scenario is the maturation rate of women vs men.

COMMENTS: The suggestion that sexual attraction to younger women somehow denotes immaturity is the same reason our planet hosts billions of human inhabitants.

In this sense, yea, we should probably all be in therapy.


“When you live as long as affluent men do, as well as they do, you can’t help but expect more out of life. A successful career is one thing, but just because you can afford beachfront property doesn’t mean you want to spend it with someone who reminds you that one day soon you’ll be buried underneath it.” Urban Dystrophy, Chapter 25, May/December.

Ronnie and Sally Wood at The Races


I’ve covered this couple in another blog [search bar], but I thought it was worth further mention, given Sally Wood’s illuminating comments.

Among them:

Speaking of their age gap, Sally told the Telegraph: ‘Um, well, I know it’s there. And I wish it wasn’t, but it is. I think I had to say “I can’t do this because of the age”, or I just had to let it go and take it all on board. At no point, years ago, did I say to myself: “I think I’ll go out with someone twice my age”, but that is what has happened.’

Up Next!

Affluent Older Men Remain Targets of Scorn for Dating Beautiful Young Women […as if we give a crap]

CIDRpEqWcAAOIPoDuncan Bannatyne, 66 & Nigora Whitehorn, 35

The fact that Bannatyne is rich and his girlfriend a native of Uzbekistan is all people need to know before piling on.

The familiar refrain from women is laced with the same tired adjectives: ““Cringe” “puke” “vomit” “creepy” in any order.

From young men it’s the all-too-familiar realization that “rich guys still get the girls.”

And feminists consider it a complete betrayal: “Women prostitute themselves and somehow betray those women who, for example, choose to tough it out in the workplace.”

I understand the vitriol, the envy.

I understand that it’s life out of order, and that it is threatening to those who want a predictable, linear story.

But that world is long gone, except in smaller enclaves outside of big cities where groups like Quakers live as people did 200 years ago.

From all of these stories – and there are more than I could possibly count in a lifetime – there are a few things I’d like to share with the detractors:

To young men —

1] Rather than hurling invective at your older brethren, you should relish the fact that in exchange for a life well lived, you earn bigger dividends down the road.

To young women —

2] For those with enough youth and beauty to barter, the 60-hour work week is a thing of the past.

To feminists —

3] Life’s a food chain.

Ageism Strikes…Again.

In this summer 2015 photo released by the Vermont Governor's Office, Gov. Peter Shumlin and his fiancee Katie Hunt pose for a photograph in Burlington, Vt. The governor's office said Thursday, Sept. 17, 2015, that Shumlin, 59, and Hunt, 31, were recently engaged and plan to marry within the next year, although they have not chosen a specific date. (Vermont Governor's Office via AP) MANDATORY CREDIT

Vermont Gov. Peter Shumlin, 59 and his fiance Katie Hunt, 31

The fact that this is a “story” at all speaks to the lingering ageism in the same world that’s witnessed Olympian Bruce Jenner morph into Caitlin, and gay marriage legalized.

So what’s up with this?

Let’s turn to some of the article’s comments for more insight:

“She doesn’t look 31. She looks older. Seems less shocking that way.”

“He must have money.”

“I would not be happy if I was her parents.”

“He’s a pig. He’s very wealthy so yeah… Right move on her part!”


There were one or two supportive remarks, but that’s it.

So what does this say about us as a society?

It says that there are lots of pissed off older women who feel left behind, and just as many young men who feel that they can’t compete with older men of affluence and power.

See, nobody’s competing with Caitlin Jenner.

The Case for Dating Men in Their “60’s”


It’s not uncommon to see successful 58-62-year-old urban men dating and/or marrying women in their mid to late 30’s.

By standards that have evolved over the past decade, 37 and 60 are considered age-appropriate.

It’s a simple formula: 1/2 one’s age plus 7.

Of course, it could also be 1/2 one’s age minus 7, and still meet normal parameters.

In either case, the women are hardly 17 for God’s sake.

With this as a backdrop, I have posted a link to an Elle Magazine article I think you’ll find interesting.

I’ll follow it’s bullet points with comments of my own based upon real life urban experience.

“Old men are polite and thoughtful and young guys are generally self-centered.” Megan Megan O’Brien, founder of the marketing agency Beauty Brander, almost exclusively dates men in their sixties and older.

Her reasons?

1] I like a man’s man.

The synopsis: “To a man in his 60’s it’s the norm to treat a woman like a LADY.”


Older men I know are far more appreciative of the young women in their lives because they know that authentic love is no longer a disposable asset.

2] They don’t play games.

The synopsis: “The bullshit factor dramatically declines as the years of their age rise.”


Time becomes a far more valuable commodity when it becomes more scarce, forcing demand through the roof. Therefore, “sealing the deal” with a younger woman becomes a far more likely outcome.

3] They are more thoughtful.

The synopsis: “Leaving love notes in your purse for you to find later is another common trait of a more mature man…..just because.”


To older men, younger women are kind of like time capsules that transport us back to a time when life was more spontaneous and carefree. Younger men have precisely the opposite effect on older women for obvious reasons.

4] They have their shit together.


The synopsis: “He’s spending more time and attention on your relationship [than at the office].”


He doesn’t have to spend as much time at the office [see#4]. Most men in this situation work from a laptop and a cellphone for a few hours and call it a day.

5] He will be proud to be with you.

The synopsis: “Most guys in their thirties think they’re doing YOU a favor by holding your hand and saying that you look beautiful.”


When you’re young, youth and beauty are boundless resources, so you take them for granted.

But older men have already been laid more times than they can possibly count, so they focus on other aspects of the relationship.

This, of course, will then lead to even more sex – only this time with someone who’s name they remember.


Two-Marriage Rule the “Natural” Course Among a Certain Demographic

Al-Pacino-and-Lucila-SolaToday’s testimonial is going to infuriate a lot of people, but what I’m about to tell you is the absolute truth.

In my world, it is commonplace for young men to marry and procreate with their college sweethearts, before divorcing them once the kids are grown, money’s in the bank, and younger women are coming out of the woodwork.

This is where the Two-Marriage Rule comes into play.


When a man reaches a certain age – and level of achievement – he expects payback.

The translation of “payback” goes something like this:

Scenario One:

“I’ve done it all: Married out of college, had kids, made money…and now what? My kids are gone, I’m semi-retired and what I’m sleeping next to looks nothing like the woman I married. But I don’t want to leave my wife because I still love her, in spite of the fact that I’m not exactly thrilled about the sex. She’s also beginning to make me feel old and irrelevant. What I need is a mistress in order to keep my marriage in tact. Then I’ll have everything.”

Scenario Two:

“I’m leaving my wife for a beautiful young woman I met at an art opening, who makes me feel the way I did when I met my current wife back at Georgetown.”


In both scenarios, the theme is the same: The man wants what he once had in order to feel the way he once felt.

Neither scenario is exclusive to men, by the way.

Women often have affairs because their own physical and emotional needs are not being met, which brings me to the question of why is everyone so damn bored?


From the perspective of older men, the reasons are academic:

1] An age-appropriate wife of 50-something is not the same as an age-appropriate wife of 20-something.

In the former, the man begins to visualize tombstones.

In the former, he gets a new lease on life with 1000 times the cash.

From the perspective of older women, the reasons are more complex:

1] While age-appropriate mates in their 50’s don’t trigger existential meltdowns the way they do in men, they do trigger boredom when men begin to take their wives for granted.


The Two-Marriage Rule

For men who marry and procreate out of college, there should be an agreement between the couple that after 25 or 30 years together, the marriage is null and void.

The couple can then decide to either renew it or walk away without financial consequence, enabling the man to live with a younger woman in relative comfort for the balance of his life [and vice-verse].


Life kinda’ sucks where marriage is concerned.

No one can be everything to everyone all the time, particularly after enough of it has passed.

People get bored, and because most of us are entitled, we expect more.

On the other hand, there are couples who are willing to age gracefully, allowing time to exact its pound of flesh without a fight.

Their expectations are more balanced, and their lives a linear trajectory that reads like a novel – beginning, middle…end.

Of course, I don’t personally know any of these people, but I’m told they exist.


While older men derive vitality from beautiful young women, older women experience precisely the opposite in the company of young men.

However, women are far better at acceptance, which they encourage in one another through their uncanny ability to bond with other women.

If men were better at this both genders would experience the same longevity, with a slight advantage to men who find young women who aren’t gold-diggers.

I’ll leave you with this article from the Telegraph:

Why Women Should be Dating Older Men in Their 50’s and Beyond…

Portrait of serious man

You might also enjoy the following Facebook group:

The Huffington Post article lists ten reasons why women should date older men.

I’ll add to the narrative:

1] Maturity

2] Gray hair

3] Good in Bed

4] Loves kids, but doesn’t want to burden you with his own.

5] Makes – and sticks to – date plans.

6] Physically fit.

7] Financially stable.

8] Knows he’s going to0 pay on the first date.

9] Well-traveled.

10] Doesn’t want you to mother him.


Okay, so for the past 4 and a half years I have lived with a woman half my age.

I’m not bragging, believe me.

Nothing is a panacea no matter what it looks like from the outside.

For one thing, it gets annoying when people refer to her as my daughter.

Thank God the ID thing finally stopped.

This is all part of the drill.

My ex was age-appropriate and often mistaken for a my mother, so we’re even.

With this in mind, why would a woman so young be interested in a man so much older?

While many will pontificate on her ulterior motives, I can assure you that she can find wealthier men all over Houston.

With this said, it boils down to the following 5 items:

1] Common interests.

We met through the art world, which means we met under circumstances of common interest, rather than a bar where anything and everything can – and usually does – happen under circumstances best left to local law enforcement.

We are also avid fitness and music enthusiasts.

When we first met I noticed that her classic rock collection rivaled mine – and mine is serious by most standards, believe me.

2] Sex.

To be perfectly honest with you [and I hate admitting this, by the way], there was a time in my life when I could not have cared less whether the woman in bed with me reached climax.

It was all about me, my needs, my conquest.

Today, it’s the opposite. It’s about her pleasure first, which I’ve found to be more fulfilling.

I don’t have anything to prove to myself beyond what I already know.

Being experienced – and appreciative –is a big deal in the bedroom.

3] Financial stability.

I know most people want to automatically make this #1, but it isn’t.

Contrary to popular belief, young woman don’t like blowing the best years of their lives on someone they’re not attracted to.

But it is also true most men in their 20’s and 30’s are still living at home, and a night on the town usually involves kegs, sliders and sports under fluorescent light.

With this as a backdrop, financial stability takes the edge off of life, and allows women time to step out of survival mode.

3] Maturity.

While some women enjoy getting wasted, sleeping with strangers, and partying all night long, others prefer a refuge from what feels like all out war to be a better alternative.

4] Knows who he is and what he wants.

When I was 27 I had no idea what I wanted to do with my life.

I liked a lot of things, but couldn’t seem to settle on any one.

This included women.

Enough said on this one.

5] Has the time to devote to a relationship. 

This one certainly ties into the 3rd item on my list, but it’s important to note that the relationship itself is on equal footing with everything else in an older man’s life.

He doesn’t have to climb the corporate ladder all over again.

This time in life is his to share with someone else.

He isn’t “on the road” every five minutes trying to satisfy the demands of a corporation bleeding him soulless.

At this juncture, he is the corporation and anyone who suggests otherwise can deal with his middle finger.


The is no perfect relationship, no matter what the difference in age happens to be.

Whether it’s an older man with a younger woman, or an older woman in the same situation, it’s all about making the pieces fit.

It’s a more conscious process than it was back in the days when a smile sealed the deal.

Now it’s about who we’ve become, who we are, and what we want.

This takes about as much of the guesswork out of life as one can reasonably expect from human beings.

For many younger women, that’s more than enough.

Rise of the “Kidult”


“Kidult” [Wiki]: In the early 21st century, there was reporting that for an adult to have interests traditionally expected only from children is not necessary an anomaly. The entertainment industry was quick to recognize the trend, and introduced a special category, “kidult,” of things marketable for kids and adults alike. Enormous successes of films such as Shrek and Harry Potter, of books traditionally targeted for teenagers and the fact that Disneyland is among the world’s top adult (without kids) vacation destinations seem to indicate that “kidulthood” is a rather mainstream phenomenon. And unlike puer aeternus, “rejuveniles” successfully marry adult responsibilities with non-adult interests. When Christopher Noxon appeared on The Colbert Report on June 29, 2006, he remarked that “There’s a big difference between childish and childlike”.


“Normal” people look at guys like me and wonder what happened?

“Is he ever going to grow up?”

“Why is he not out-of-shape?”

“Why doesn’t he have an age-appropriate girlfriend? Is he intimidated by women his own age?”

“Is the young woman in his home a gold-digger, or did her father not love her enough?”

“Why doesn’t he have children?”

“Is he too selfish, narcissistic and self-absorbed to share his life with others?”

“Why doesn’t he dress more conservatively like other men his age?”

“Why does he dress like that?”

“Why doesn’t he think like we do?”

“Why is he trying to be 20 all over again?”

Oh lord, I could go on…


To be perfectly honest with you, I have always been this way.

For one thing, I have always been my own man.

I worked for myself, set my own schedule, led my own life.

All I had to do was be good at what I did, treat my clients well, and pay a CPA to keep me out of jail.

After a while the freedom and independence this afforded me became part of my identity.

The lifestyle made me more resilient, self-reliant. Those acquired attributes are just part of the process of independence.

And while it hasn’t always been easy, the pay-off covered the periodic turbulence–10-fold.

To all the men my age who continue to live life as fully–and intensely–as we did back in the day, congratulations.

You’ve officially earned a legion of haters who wish they had the balls to have done exactly the same thing.

It takes courage to grow up and become who you really are.

~ e.e. cummings


For more reading on this topic, the following article by Robert Firestone Ph.D. is illuminating.





Typical habitat of the “Kidult.”