Okay, so eightysomething Hugh Hefner and his twentysomething girlfriend number one Holly Madison have apparently called it quits because he refused to allow her to weasel her way into his will so she could be supported for the rest of her life. I’m sorry, I phrased that wrong. I mean, they broke up because he didn’t want to marry her and knock her up.

Anyway, I learned of this tragedy by reading the most pathetic story ever in which Hugh admits to being “down in the dumps” over the split despite the fact that his personal assistant Mary (who is much closer in age to Hef) promised him that there is a bevy of young girls who are willing to be his new girlfriend(s).

Holly Madison is apparently taking the split in stride as she and Hef’s two other girlfriends (Bridget and Kendra) work on spin-offs to their E! reality show “The Girls Next Door.”

Who’s next on Hef’s radar? Apparently, 19-year-old twins Karissa and Kristina Shannon are living in the Playboy Mansion and are poising themselves to be the very last girlfriends Old Man Hefner will ever have. Hope they brought extra Depends.

In the article’s wistful and uber-pitiable last line, Hefner insists, “It’s a big house. And I’m not going to live alone. I’m definitely not going to live alone.”

Am I the only one who sees this as so miserable it ceases to be funny? Here is a man who is essentially being used by young women as a way to advance their careers while a woman who is his age and who has been by his side for most of his life (Mary) is reduced to a mere employee because she doesn’t have fake tits and blonde hair. Meanwhile, girls spend the best years of their young lives pretending to enjoy sex with a man who must have to have Viagra on a continuous IV drip in order to get it even halfway up.

I’ve heard lots of people say that plenty of dudes would love to be in Hugh’s position when they’re 80 years old, and I’ve heard plenty of other people say those girls know exactly what they’re doing when they move into the mansion. It’s a win-win situation for everyone, they argue. And I suppose that could be true. But can I just say I am so glad I spent my twenties making out with hot young guys, and now that I’m an old married lady, I’m so glad I get to get old with someone?

Talk about win-win.

— Jennifer Mathieu

This article appears in Oct 9-15, 2008.