Sugar Daddies vs. Sugar Babies

Ask me on any random day to list the Top 5 People I Respect and you're bound to get a slightly different answer. However, usually the list will include some combination of Kenneth Copeland, Al Sharpton and Anna Nicole Smith in no particular order.

You see, I love a good old fashioned hustler. And while the two aforementioned gentlemen are certainly pillars of game, perhaps no one in history has been more shameless about the relentless pursuit of self-enrichment no matter the moral cost than Anna Nicole Smith.

Now is the time I should probably admit I was Today Years Old when I found out Anna Nicole Smith has been dead for 13 years. Talk about an absolute gut punch - brutal way to start the weekend. That said, I REALLY enjoyed those first two paragraphs, so the blog will proceed as planned.

For my millions of high school readers who may not be familiar with Anna Nicole Smith, a quick synopsis. AnNiSmith, as her loyal fans call her, was a former 1993 Playboy Playmate of the Year. With a simple Google search, one can get very familiar with her work.

While most people would be content to rest on those laurels, Anna was very clearly not 'most people.' Her life's work reached it's apex in 1994 when she married oil billionaire Howard Marshall. At 89 years young, Howard was a measly 62 years his bride's senior - a tiny gap any reasonable and committed duo could easily bridge. The happy couple is pictured below on their wedding day - clearly so in love and excited to get married, they literally couldn't wait for their guests to arrive.

Sadly, ol' Howitzer Howie died the next year in 1995. A completely unnecessary and offensive court battle ensued between AnNiSmith and the State over the rights to Marshall's estate, which obviously should should have been 100% hers to take. The case ascended all the way to the Supreme Court, and went back and forth for years. I won't get into the details of the various settlements (mostly because I don't understand them), but suffice to say Anna got screwed. Her infamy and resulting media coverage from the whole affair proved much more lucrative than the actual marriage ever would. She died in 2007 - rest in peace, sweet princess.

Which brings me to the real topic of today's blog. You see, while Anna was an especially shameless and devoted pioneer, she was certainly not the first and absolutely would not be the last. The world is rife with these kinds of arrangements, 93% of which are confined to Hollywood (which has done a phenomenal job of convincing us peasants how normal and healthy such relationships are). My favorite recent example was Dennis Quaid (66) marrying some 27 year old vixen (pictured below). The marriage was a perfect bookend to the actor's career, whose most noteworthy role was 2002's The Rookie. A film about a way-too-old pitcher who still had his fastball and found his way into the Big Leagues. Har har har. Nice job, Quaider.

My question is simple - and I genuinely mean this out of pure curiosity: Which half of these picture-perfect couples have the more embarrassed family/friends on wedding day?

Before we get to the answer, just in case your finger is hovering over the big red CANCEL button: This question goes both ways. Don't think for one second I forgot about the female Sugar Mommies. I see you Madonna! Though to be fair, the women are usually much smarter than the men and ditch their pool boy play toys before actually tying the knot and giving them any access to the trust fund.

For the sake of the argument, let's throw out the "who is paying for the wedding?" factor. We'll assume it's the sugar daddy/mommy - money isn't an object. We'll also say that no pre-nup exists.

Since I am in fact a man, I'll put myself in the two most noteworthy male wedding positions: Father of the Bride, and the Groom's Best Man.

FATHER OF THE BRIDE:

On one hand, you're probably happy that your little girl will be financially taken care of for the rest of her life. There's nothing worse in 2020 than a late 20s / early 30s daughter who still is on their parent's phone bill and needs rent money. Business decision wise, it's a smart move.

That said, it has to be hard knowing that everyone thinks you raised a soulless gold digger. Not saying that love can't exist across generations - but let's be real. It's rare. Self-doubt creeps into your mind, and you wonder where you went wrong. Did she learn nothing about Greed in Wednesday night CCD classes??? Passing your little baby off to the grinning son of a bitch who looks like one of your poker buddies and knowing that he could buy your house with his pocket change has to be emasculating. He's the captain now.

You probably have to get blackout drunk and challenge him to a shirtless wrestling match at the reception. It's likely your last opportunity to assert your dominance in front of your daughter. Adding insult to injury, he pins you faster than a Rick Pitino restaurant romp and doesn't even have to straighten his tie. You take the black SUV car service (which he paid for) home while your wife sits in the front seat Googling divorce attorneys. EMBARASSMENT LEVEL: 8.4 / 10

THE BEST MAN

If you're under the age of 25 (you're not) you might think getting married to some young hottie is TOTALLY BADASS. You might even be jealous of your best friend. Damn - what I would give to lock down a tasty babe like that! Neat! And to be fair, you'd be right. For approximately 26 days.

Then reality hits you, and you realize your boy will likely be bankrupt and an alcoholic by the next election cycle. She will posterize him quicker than Jordan on Alonzo Mourning. Send him into an uglier retirement than Lamar Odom.

You beg him to back out. You spent $3,000 at the Vegas Spearmint Rhino hoping he'd fall in love, but the procedure didn't take.

Now everybody thinks you're a bad best friend. You get up there for the best man speech sweating like a pig in a butcher's shop. You simply cannot joke about the obvious in front of the woman's family. Everybody knows you're fuller of shit than a Coachella port-o-potty. You say some sweet nothings about honor and trust and devotion and sit the fuck down. The idea of this guy waking up next to this girl as she farts her way though a Tik Tok dance while he goes to work has you reeling in second hand embarrassment. Everybody is thinking "what an idiot". But at least you're not him. EMBARASSMENT LEVEL: 5.6 / 10

It's settled - the Dad by a country mile. Hug your friends and daughters, and have a great weekend.