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).

Imagine you’re a beautiful shining star, luminescent and bright, sending beams of radiant light and energy out into the universe for millions of light years. You are impressive and unforgettable in every way, but an astronomer has yet to discover you. The only thing standing in your way of being noticed is that you are surrounded by tens of thousands of other bright, shiny stars.

Sugar Babies are a lot like undiscovered shining stars; they are beautiful, unique and radiant, but they are surrounded by thousands of other Sugar Babies trying to attract the attention of that perfect Sugar Daddy.

Her bikini is already packed

If you know what Sugar Daddies look for in Sugar Babies you’ll be able to set yourself apart from the rest of the thousands of other shining stars in the night sky.

Sugar Daddies Want Convenience

Convenience and efficiency constitute the driving force behind Sugar Daddy Dating. Remove either one of these elements and the Sugar Daddy, as well as the Sugar Baby, are back to throwing darts at a board.

Stress the convenience of your situation when corresponding with your Sugar Daddy. Use terminology like, “available for spontaneous get-togethers,” or “my bikini is already packed.” As always, be yourself and make sure your personality comes through in the process.

Sugar Daddies Crave Approval

The Sugar Daddy is usually a self-made man, nothing was ever handed to him and the reason he has attained a certain degree of success is because of innovation, dedication and concentration. Express an interest in his business pursuits without being too invasive and let him know you’re impressed.

Sure he may have made his fortune in coat hangers or tube socks, but an empire is still and empire no matter how you slice it. Give your Sugar Daddy a pat on the back, or at the very least, an understanding nod. Acknowledge his accomplishments and it will come back to you ten-fold.

Sugar Daddies Require Certain Skills in a Sugar Baby

Beauty will get your foot in the door, but the Sugar Baby who can spin more than one plate at a time ups her appeal and her longevity.

By talent we’re not referring to your ability to debug a home computer.

Sought after Sugar Baby talents include;

Keen Fashion Sense – Sugar Daddies generally don’t have time to keep up with what’s hot and what’s not in terms of fashion. Demonstrate your ability to navigate the men’s department at Barneys or Nordstrom’s and you’ve been promoted from Sugar Baby to fashion consultant. This particular skill set works on several levels because if you’re shopping for him, well, you’re not going home empty-handed either.

I-Phone Blackberry Proficiency – There is no single greater aggravation to a Sugar Daddy than the non-texting, no e-mail having, technologically illiterate Sugar Baby. The Sugar Baby/Sugar Daddy dynamic hinges on text messages, e-photos and other quick, short and sometimes erotic communications. Keep up with the latest in e-communications.

Activity Planner – Sugar Daddy’s are busy people, and without the right Sugar Baby to show them how to have a good time there is a distinct possibility they’re going to miss out on all the fun. It’s up to you, the free-spirited and vivacious Sugar Baby to know the best clubs, restaurants and romantic hideaways. Show me a Sugar Baby who knows where to rent Jet Ski’s at 11:00 p.m. on a Friday night at the Jersey Shore and I’ll show you a Sugar Baby who’s got wealthy suitors lining up around the block.

Sugar Daddies Love Independent Sugar Babies

No one likes clutchers. Sugar Daddies in particular are dynamic and independent, and since like attracts like, it only makes sense that the Sugar Baby who resides at the center of her own universe is going to get the guy. Independent Sugar Babies bring excitement, experience, charm and social skills into the equation.

Sugar Daddies, wealthy men, established men, call them what you will, have discriminating taste and are fiercely competitive. They need to know they’re getting the very best.

Plan your moves, exercise your creativity and blow them all away with your newfound Sugar Baby talents. You’ll be happy you did.

My Mother was the epitome of old world conservative, or so it seemed until you met her Mother.

My Grandmother loved to tell stories about how she conveniently lost messages when “boys called on the phone” for my Mother. As far as she was concerned, suitors were supposed to come for family dinners and dates were supposed to be chaperoned. My Mother had her own ideas.

In the Sugar Daddy dating scene, going online will get you ahead

My Mother, in turn, believed it was irreverent for my sister’s dates to honk when they pulled into the driveway as opposed to coming to the front door and introducing themselves. The reality of the situation was that they were just terrified of my Father, and rightfully so.

The one thing the two generations had in common is that their perspective on how men and women were supposed to interact was steeped in dogma and outright ridiculousness. How anyone had five minutes of fun under those circumstances is a mystery.

There are 6,000,000,000 people on the planet, give or take, and the only thing that the average man or woman needs in order to be happy is to connect with about ten or twelve of them (500 to 1,000 if we’re talking about Charlie Sheen).

We don’t drive to work in horse-drawn carriages anymore, doctors stopped using leeches to cure headaches a while ago and we now know that the Sun is going to rise every morning whether or not we pray to it.

The dating concept deserves the same upgrade as every other aspect of Western civilization.

The Sugar Daddy scene is dating perfected. It’s effective, safe and delivers what it promises. The pretense, posturing and misrepresentation of hit-and-miss dating have been removed, leaving the Sugar Daddy and Sugar Baby alike with pure, unadulterated expression of mutual needs.

Last time I checked honest communication was supposed to be the cornerstone of successful relationships.

Sure, Sugar Daddy dating is all about NSA (no strings attached), but in reality two people having the time of their lives on an adrenaline-fueled thrill ride are more likely to find romance than two people on a date chaperoned by my Grandmother.

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.