This marriage proves pretty surprising, considering Hefner’s rather public dismissal of holy matrimony when former girlfriend, Holly Madison, was attempting to cement her acquisition of the legendary sugar daddy. Madison sought just three things, a baby, a diamond ring as big as her boobs, and a promise that she would be rich forever. Too bad she received none of those things. So Holly and Hefner went their separate ways. Enter a new set of girlfriends: Kristina Shannon, Karissa Shannon, and the bride-to-be, Crystal Harris. In truly classic playboy fashion, it was out with the old and in with the new.

Kristina and Karissa, the twenty-year-old twins who took the place of Bridget Marquardt and Kendra Wilkinson, didn’t stick around for long. By January of 2010, the girls had moved on from their then eighty-three year old boyfriend, leaving just Crystal Harris to keep the sugar daddy company.

Typically, Hefner kept his mansion stocked with beautiful women to snap up the previous girlfriend’s position whenever one left, but this time, he left it with just him and Crystal. It didn’t take long before the two had established a monogamous, one-on-one relationship that led to an engagement in December 2010.

Although the sugar daddy lifestyle as Hugh Hefner knows it has concluded, his sugar daddy ways are far from over. Hefner, at eighty-four, is more than sixty years older than his twenty-three-year-old fiancé. Furthermore, you can bet that Crystal Harris will be up to her fake breasts in diamonds, pink golf carts and tiny puppies as long as they both shall live. The excellent news for Crystal Harris is that even if their marriage doesn’t work out, Hefner has refused to sign a prenuptial agreement. That means, even if they turn into enemy exes, he’ll still be her sugar daddy. It looks as though Hefner will continue to be a sugar daddy, but, for now, now he’ll be a monogamous one

The sugar daddy officially gives up bachelorhood in June of 2011, ruining the dreams of playmates everywhere. Good luck to the future Mr. and Mrs. Hefner and here’s hoping that, this time, it works.

To the average person, it would seem that this was not Charlie Sheen’s year. If any other American man got himself axed from career that managed to keep him relevant and paid him more money than he could ever spend in fifty-seven lifetimes, he would probably cry himself to sleep. Not Charlie, though. Charlie did what any respectable forty-something celebrity would do. He went off the deep end, ranting and raving to anyone who listen (and televise) and tried to turn his somewhat mediocre television career into a stand-up comedy routine. He did something else though, something far more interesting and newsworthy. Charlie fetched himself a pair of earthly goddesses to spend his money and feed his sexual appetite.

Basically, in Charlie’s own words, he’s winning. To sum it up, yes he lost his job, but on the other hand, he has too much money to know what to do with and a new set of blondes to help him with that pesky problem. He doesn’t need any more money and besides, he’ll probably be making royalties off the reruns of his portion of the show for a very long time. No worries for Charlie as he has his money and a pair of hot blondes to boot. It looks like Charlie knows what he’s talking about, he really is winning.

Oh yes, Charlie Sheen has a real shot at becoming the best of all sugar daddies. He’s starting out relatively young. He’s only in his forties, you know. Furthermore, he’s already been practicing for some time. His second wife, Denise Richards, is a solid five years younger. Not necessarily impressive, but it was a first step into sugar daddy stardom. His third wife, Brooke Mueller, is twelve years younger. This marriage proved something; maybe Charlie Sheen was still wearing floaties, but was ready to jump into the deep end of the pool. The goddesses, Rachel and Natalie, tore those floaties off and jumped in the pool with him as they  both come in at twenty-four, a solid twenty-one years younger. It seems like not only is Charlie winning, he’s winning the jackpot.

Sure there are still six more months left in this year, but it’s a pretty indisputable win for Charlie. It looks like there can be no competition for this sugar daddy of the year. In fact, there may never be competition, once Hugh Hefner is officially off the market this summer. The only opponents that Charlie will have to watch out for are his two boys, Max and Bob. Growing up in that household is almost certainly going to prime them for the future. Watch out Charlie, you’ve got twenty years before you’re served up a double dose of the only thing that could tear you down from your pedestal.