Cougar Hunters: 10 Celebrities Who Love Dating Older Women

Age ain't nothin' but a number in Hollywood—as the celebrities on this list clearly demonstrate. We often hear tales of age gaps between high-profile couples, but there are a select few male stars who have made cougar hunting a veritable pastime. From George Clooney’s heyday to Nick Jonas today, here are 10 actors who just can’t seem to stay away from their older female counterparts.

Now, while sometimes these age-gap relationships last for eternity, other times (read: most times) it just doesn't work out. So if you're ever feeling the urge to find yourself an older woman in the limelight, here are a few famous fellas who have gone down that path before. 

Here are 10 of Hollywood’s most notorious cougar hunters!

Ashton is currently happily married to Mila Kunis, but before they reentered each other's lives (after originally meeting as kids on That '70s Show), Ashton was famously married to Demi Moore for eight years—which is a lifetime in Hollywood. As she recounted in her 2019 tell-all, “He was 25. I was 40. But I'm telling you: we couldn't feel it."

In 2011, they decided to end their marriage; they were separated for a year before the divorce was finalized. Ashton was accused of cheating on Demi several times, but reports were never confirmed. Turns out a 15-year age difference might not be the easiest thing for a couple to navigate.

Before finally finding true love with Jessica Biel, Justin Timberlake had to date around a bit. He dated actress Cameron Diaz from April 2003 to December 2006, and with an age gap of eight years between them, it's kind of remarkable that it lasted that long. Whether you found it endearing or eyebrow-raising at the time, now we can all look back and laugh (in a friendly way) when we realize that his current wife is actually two years younger than him!

He also dated several other famous older women, including Alyssa Milano (eight years older) and Fergie (five years older)

Nick Cannon and Mariah Carey's marriage lasted for six years—though maybe it seemed longer due to the 10-year age gap between them. But it all ended in 2014 when Nick Cannon decided to, ahem, spread his paternal wings and have children with other women.

Since then, he's become the king of multiple paternity suits and even expanded his mogul status by fathering multiple children in a single year...right after pronouncing himself celibate! Including the twins from his marriage to Mariah, his current total of kids is 12—with six different women. Honestly, you can only admire both his work ethic and...reproductive skills?

Ben Foster and Robin Wright have had a tumultuous relationship over the years, with the sizeable age gap (15 years!) between them likely complicating matters even further. This extraordinary couple met on the set of 2011’s Rampart, and despite separating briefly in 2014 and 2015, they seemed to be going strong—until they announced the end of their engagement in 2020.

Foster and Wright have moved on from each other since ending their long-term relationship. Ben, who first rose to fame in films such as Hostage, Alpha Dog, and X-Men: The Last Stand, is now married to actress Laura Prepon, best known for her cult-classic TV show That '70s Show, as well as Orange is the New Black. On the other hand, Robin Wright has found love with fellow actor Clement Giraudet, the luxury fashion executive at Saint Laurent Paris.

Ryan Gosling, the dreamy star of The Notebook, has dated several older women, including Sandra Bullock (16 years his senior). After meeting in 2002, their relationship only lasted 18 months before the stars went their separate ways.

But almost a decade later, Ryan began a romance with another older Hollywood star - Eva Mendes (six years his senior). Fast forward, and the two are still together; the couple has two beautiful daughters together. 

Derek Hough is an internationally recognized Latin and ballroom dancer who found his way to fame through the popular show Dancing With the Stars. He dated actress and model Shannon Elizabeth—12 years his senior—for some time in 2008.

He was also rumored to have dated the beautiful Kate Hudson, who's just five years his senior, after her split with Matt Bellamy in 2014. He's since retired from hunting cougars, however; he's currently engaged to Hayley Erbert, a 28-year-old dancer he met on Dance With the Stars that same year.

Aaron Taylor-Johnson and his wife, Sam Taylor-Johnson, who is twenty-three years his senior, continue to prove that age is nothing but a number. The couple met while working on the film Nowhere Boy—Samantha was the director, and Aaron starred as John Lennon when he was a teenager.

They've since been married for more than a decade and have two daughters and one son together, who at times have starred in their mother’s works. While people’s opinions may vary about the age gap within their marriage, it has only grown stronger with time and has set an example for couples around the world—you're never too young or too old to find love!

Despite being one of the greatest guitarists in Hollywood, John Mayer is arguably more famous for all the famous women he's dated and scorned. And while he's become famous more recently for dating women who might be too young for him (Taylor Swift called him out in her 2010 hit, "Dear John" and again in 2022's brutal "Would've, Could've, Should've"), in his younger years, he had a reputation for dating older women.

He dated Cameron Diaz, five years his senior, in 2007 after her breakup with Justin Timberlake, and then Jennifer Aniston, eight years his senior, from 2008-2009.  And it sounds like age had everything to do with the latter breakup; he told Playboy in 2009 about Aniston, "I'll always be sorry that it didn't last. In some ways, I wish I could be with her. But I can't change the fact that I need to be 32."

Nick Jonas, of The Jonas Brothers fame, has dated several famous older women, including actress Kate Hudson (13 years his senior) and Australian actress Delta Goodrem (18 years his senior, sheesh). His relationship with Kate was very brief, but he dated Delta for almost a year before they decided to part ways. 

He briefly dated Olivia Culpo, actress and Miss Universe 2012, who is actually his exact same age. And he's now quite famously married to Priyanka Chopra, who is the youngest of all the cougars he's dated—a decade his senior. The two welcomed a baby via surrogate in January 2022. 

Tony Parker, the famous French NBA player, was married to the stunning Eva Longoria, seven years his senior, for four years.

The two were deeply in love for several years before Tony’s affair with his teammate’s wife (Erin Barry, the wife of Brent Barry) came to light in 2010, which inevitably lead to a rather messy divorce.