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A Pictorial Review Of Famous "December" Women

By Mieka Strawhorn | Celebrity | July 31, 2018 |

By Mieka Strawhorn | Celebrity | July 31, 2018 |


There’s nothing notable, new, or exciting when you see an old ass dude with a woman half his age dangling from his arm. Starting at about middle-age, men can legally date a “halfer” with nary an eye batted. Case in point: 43-year-old Leonardo Dicaprio recently enjoyed a yacht trip in Saint-Tropez with his 21-year-old girlfriend Camila Morrone and her mother, 42-year-old Lucila Sola whose boyfriend, Al Pacino, is 78! In Hollywood, as in real life, the May-December romance (or even in some cases, April-January) between an older man and a younger woman, is evergreen.

It’s a creepy dynamic that’s prevalent the world over — for reasons we’d probably all rather not think about too much. Yet, when the script gets flipped, and you see a woman “d’un certain âge” strutting around with some young buck at her heels, it comes off as a baller move rather than a clichéd inevitability.

In Hollywood, women who tend to date men much younger than themselves, often display outrageous and exhilarating levels of dontgiveafuckatude. There’s probably a lot to be said here about overcoming the power dynamics of men declining to date a woman more successful/rich/talented than themselves. But that’s for a Sociology Today article, not this stupid post I wrote as an excuse to look at a bunch of sexy pictures of Cher leading Val Kilmer around by the elbow. Cher herself has said that the reason she dates younger men, is that they aren’t intimidated by her. Men her own age just can’t deal with her Cher-ness. So for Cher, it’s not so much a preference, it’s who’s willing to stand in her shadow.

Before we move on, please let us dispense of the term “cougar.” It’s stupid and pejorative. These women aren’t predators, and they sure as hell aren’t hungry or desperate. How gross would it be if we decided to call Leo and his ilk “lions” because they stalk young women? I mean, I guess animal-wise, Leo the Lion is a bad example, but you get my point. When all parties are of age, what’s good for the goose, is good for the gander.

Here’s a gallery of famous women who weren’t trying to wait around for some middle-aged putz to work up the nerve to ask them to dance.

Heidi Klum is currently dating 28-year-old Tom Kaulitz who is in the band Tokio Hotel. Heidi is 17 years his senior. It’s not the first time Heidi’s opted for some younger strange. She dated now 33-year-old Vito Scnhabel for three years.


Speaking of Vito, he was once with serial younger-man-haver Demi Moore. Here’s Demi with her now ex-husband Ashton Kutcher, who is 15 years her junior.


Did you know that Joan Collins is 31 years older than her husband Percy Gibson!? They’ve been married since 2002. Also of note, Joan will have a role in the upcoming 8th Season of American Horror Story. The Dame’s still got it!


Another legendary Dame, Elizabeth Taylor, also had a much younger man later in life. Larry Fortensky and his feathered mullet were married to Liz from 1991-1996. Liz was 20 years older than Larry. Here’s Liz, Larry, and Sir Elton John.


Jennifer Lopez and Madonna are both prone to the particular charms of a younger man. Here’s Jenny From The Block with 12-years-younger Casper Smart. She’s now engaged to Alex Rodriquez who is only 6 years younger.


Madonna also used to date A-Rod and Madonna is 10 years older than JLo. I’m very bad at math, so you do it this time. Here’s Madonna with a model she may still be dating, Kevin Sampaio, not giving a single fig that he is 27 years younger.

Gabrielle Union is 45 and her husband, NBA player Dwayne Wade, is 36. The age gap isn’t very big but I just really love her outfit in this picture.


After being married to Sean Penn, who could blame Robin Wright for seeking a man with slightly less baggage. She was engaged to Ben Foster who was only 2 years old when Fast Times at Ridgemont High came out (and 14 years younger than Robin). Now she’s with a super hot French fashion executive named Clement Giraudet. But since he’s European the internet won’t tell me how old he is. Which is good really. It’s none of our business.


She’s happy, he’s happy, and age ain’t nothin’ but a number.