25,000 B.C., Tuesday

Cave paintings discovered in Lascaux, France depict two cave men. The first one is being berated by his unruly cave wife for being a lousy hunter and the second one is draped in animal pelts, surrounded by adoring cave hotties (also draped in animal pelts) who are ambitiously working to satisfy his primitive Sugar Daddy needs.

Ironically, a second set of cave paintings from the same region depict the aforementioned disgruntled cave wife living large in the upper west side after her divorce attorney got through shellacking her non-pelt-providing cave husband.

134 A.D., The Golden Age of Rome

Roman Emperor Antoninus kicks Sugar Daddy dating up a notch when he commissions the city’s top engineers to invent the hot tub, the smoking jacket and Vodka. Following in his steps future Emperors go on to pioneer the creation of the convertible, the American Express Platinum Card, the cigarette holder and Jello shots.

922 A.D. Feudal Japan

Japanese men realize that the guy who can afford the best rice wine and fish heads is the same one hogging all the best women. They band together to form an elite ruling class called the “Sake Daddies” and vow to win these women back by showering them in silk robes and pearls – the Geisha is born!

The Sake Daddies also hire artisans to carve thousands of small ivory sculptures in order to immortalize their exploits. Go figure.

Henry VIII, The King Of Hearts?

1522 England

Henry VIII showed western civilization how a real Sugar Daddy lives by initiating what will later become known as “the rotation.” Henry kept so many Sugar Babies waiting in the wings that HBO eventually gave him his own series. He had a good run but died, not from loneliness, in 1547.

1790 America

Yes indeed, George Washington was a PROLIFIC Sugar Daddy. He was also so adept at keeping his arrangements on the down low that the only things history remembers him for is chopping down the cherry tree and having wooden teeth.

George’s single greatest contribution to the Sugar Daddy lifestyle was establishing the “Don’t ask, don’t tell” policy. After a few pints he was known to quip to friends that “What Martha doesn’t know won’t hurt her.” Washington also pioneered the concept of Brown Sugar which the Rolling Stones later immortalized in their classic hit.

1876 Cambridge, Massachusetts, United States

Once again, sex is responsible for the greatest invention of the 20th century, the telephone. Alexander Graham Bell realized that if Sugar Daddies were to live the lifestyle with any degree of convenience, they were going to need a quick and easy way to contact their Sugar Babies without dispatching a loose-lipped courier or taking a high-profile carriage ride across town.

Although married to Mabel Hubbard for more than 45 years, Bell learned early on that tech geeks make the best Sugar Daddies. Legend has it that he preferred the pay-as-you-go approach for his Sugar babies as opposed to a fixed monthly budget due to the fact that he was busy fighting off more than 600 lawsuits that challenged his patent on the telephone. However, it should be noted that he later went the extra mile and invented the metal detector after one of his playmates lost her custom broach during a romp in on Mass beach.

Is the Jackie of All Trades better than the dream team of specialist Sugar Babies? Is it more enjoyable to have one Sugar Baby that can ski the black diamond slopes as well as she can fill out a Brazilian t-back, or to have a virtual arsenal of Sugar Babies, each one equipped with her own special skill set?

Multiple Choice

The answer to that question depends on the Sugar Daddy and of course, the depth of his pocket. For the average man, handling two women is like trying to drive two cars, it sounds great on paper but there is a lot of stopping and starting.

But the Sugar Daddy is anything but average. He is the master of industry, the man who made his first million before he was 30, the very same guy who got his pilot’s license just because the grouper in the Bahamas tastes better than the variety they serve in Miami.

Of course more is better. Or is it?

Lance (not his real name) has been seeing the same Sugar Baby for two years. He’s the out-of-town guy that shows up like Santa Clause when he wants to unwind. The majority of nights with his girl are spent out on the town, not clubbing till 5:00 a.m. but more along the lines of wine bars and Jazz clubs. He likes the stability and the consistency of the relationship.

Did I mention that Lance is also happily married with two children?

“I really don’t want to start talking about right and wrong here,” Lance said candidly. “All I can tell you is what works for me. Having more than one Sugar Baby would be ludicrous. Jasmine (obviously not her real name) is my solace, my getaway and someone I trust to keep our arrangement just between us.”

A lot of Sugar Daddies are like lance. They don’t need to be the king of Sugar Mountain, but they still like the arrangement scene. For the record, Lance’s marriage is rock solid by all practical definition. He has no intention of leaving his wife or leaving Jasmine (still not her real name). He’s a happy man.

Lance has a rather consistent financial arrangement with Sugar Baby. He deposits a specific amount of cash into a checking account every month and that takes care of Jasmine’s rent, phone and essentials. When he comes into town there are nights out, some shopping, but it’s a rather conservative deal.

Which brings us to Cameron. He’s got a lot of time to fill since selling his software company but now he lives his life like he’s the subject of a documentary on living like a rock star. For Cam, the cameras are always rolling.

He’s got a Hatteras that costs more than most people’s homes, has never been married (and seems to be keeping it that way at least for the foreseeable future), and has lots of friends. His only Achilles heel is boredom.

Cam keeps three Sugar Babies in rotation at all times. He’s the perfect delegator. He’s got a travel baby, a club baby and even one he keeps around because she’s a deep water certified scuba diver (really). For a stretch there was even one Sugar Baby in the mix whose sole qualification was that she was a Maxim Girl.

He’s not exactly paying the freight for all three but they all do very well. It’s a pay-as- you-go arrangement as opposed to a defined monthly budget. The girls make out with lots of news clothes, spa days, salon days, flat screen TV’s, bathroom renovations, and anything else you can think of that costs money.

“I’ll admit I am a chronic type A,” Cam Said. “Whether I’m working or playing it’s at full speed. It’s just the way I am.”

As unorthodox as either arrangement may sound, it’s all a matter of perspective. If they were to switch places even for a brief period of time, Cam would be so bored he’d start another software company and Lance’s head would just explode.

So in the end, which arrangement is better? The answer is both and neither. It all depends on the Sugar Daddy and what he’s looking for out of his arrangement (or arrangements).

There’s a first time for everything, but letting on that you’re the rookie never helps. Experienced people, especially wealthy men, only want to associate with other experienced people. Confidence is the key, and a little role playing doesn’t hurt either.

EVERYONE acts and postures, especially in business and social situations. People act like they don’t care when they really do, they act like they’re millionaires when they can’t even pay for lunch, and they act as if they don’t have a problem in the world when they’re really knee-deep in crocodiles.

Know How To Fake It

Fake it until you make it. If you come off like a bumbling geek you run the risk of being the little girl in the school yard with pigtails and braces that no one wants to play with.

Know what people are going to say before they say it and you’ll gain a formidable advantage. Give a little thought to the questions that may come up in conversation with your rich Sugar Daddy at the formative stage of the arrangement.

In any given dynamic, people ask the same five to seven questions at the very most. In your case, there are only one or two questions you need to prepare for so as not to be exposed as a novice. For instance. . .

How long have you been a Sugar Baby?

This is a good one because it’s probably the most commonly asked. Go for something whimsical and don’t take the question too seriously.

“My whole life.”

Great answer! It sets the tone for the relationship and lets Sugar Daddy know you’re serious about being taken care of. Also try the reversal;

“How long have you been a Sugar Daddy?”

This is also a dynamite response because it gets Sugar Daddy talking about himself. Men, above all else, love to talk about themselves.

Possibly he may ask. . .

“Do you do this type of thing often?”

No problem, it’s a variation on the same question. Once again, humor works best.

“Not often enough apparently.”

You just knocked it out of the park. Sugar Daddy is riding high because you just stroked his ego and you came off smoother than Mata Hari. You’re officially running the show.

Another great tactic is to take the initiative and jump in before Sugar Daddy starts asking questions.

“So, do you seduce many women or am I special?”

You may initially think you can’t say this without laughing; it’s a line by every definition of the word. However, with just a little bit of practice it’s a lethal opener. You’re grabbing the high ground and simultaneously giving Sugar Daddy the opportunity to compliment you on how special you really are. It’s a loaded question. You already know where the conversation is going.

Take advantage of every situation to shroud yourself in mystery. Be aloof, create the persona you want to be. You’re embarking on a fresh start with a new benefactor so make the most of the opportunity.

When the Good Ship Sugar Daddy leaves the dock and an enviable arrangement has been established, give yourself a pat on the back for being a consummate professional.

Best of all, you’re only a rookie once and you’ll never be that little girl with pigtails and braces again.

Whoever said you can’t have it all was probably the same person who said money can’t buy happiness. These are two legendary rationalizations designed to keep everyone suspended in a state of perpetual malaise. In reality, you can have the best of both worlds without sacrificing your integrity.

Our parents raised us to believe that you can’t buy love, well you can’t. But unless you’re able to get out there and interact with a variety of people, love isn’t going to miraculously roll up upon your doorstep. But whether it’s love or a scorching NSA thrill ride that you’re looking for, the fact of the matter is that things cost money.

The Best Things In Life Aren't Usually Free

Sir Mix-A-Lot, probably one of the greatest philosophical minds of the 21st century, put it best when he wrote, “The honey gets runny when the money gets funny.”

So who are you going to listen to, your parents or Sir Mix-A-Lot?

An old business cohort of mine was one of the shallowest, narcissistic pigs ever to walk the earth. He had medium good looks, liked to work out so his body was solid, but he was completely unremarkable. However, he always had the hottest looking girlfriends. His secret; spend, spend, spend.

Howard (maybe his real name, maybe not) paid for EVERYTHING. He was the first guy I ever knew who bought a car for a girlfriend. It was a lease actually (the car not the girl) but that was only a small part of his largesse. He bought so much jewelry for his dates that a rep from the jewelry store would come into the office once every couple of months with a suitcase full of baubles and booty for Howard to stockpile. His spending was grandiose but completely premeditated.

There were weekends in Cabo, $700 dinners in the middle of the week and NUMEROUS shopping sprees. We all thought he was nuts.

Ironically, his money served as an effective vehicle that allowed him to gain repeated exposure to some of the classiest, most sophisticated women in the city. After years of pushing misogynism to the absolute limits, some class and manners actually rubbed off on the guy. He eventually hung up his six guns and married an Elle Macpherson look-alike.

Last I heard they had two kids and were doing just fine.

The point is that Howard wasn’t looking for love, and the girls who dated him were just into him for the money and the excitement, but the dynamic he created (unintentionally) set the stage for an inevitable romance. You can only rub two sticks together for so long before they catch fire.

So the moral to the story, if there is one, can be interpreted a few different ways.

One way to look at it is that Howard was a schmuck who burned through a lot of cash because no woman in her right mind would date him. The fool was repeatedly separated from his money in an irresponsible spending spree that lasted through three presidential administrations.

Another way to look at it is that Howard was lucky enough to be able to pay for an Ivy League education in how to treat a lady right.

Not every man needs to run out and embark on a wild Sugar Daddy spending spree like Howard, but maybe, just maybe, if a guy repeatedly complains that he can’t get a date, he just might be spending his money in all the wrong places.

Live a little and the possibilities are infinite.