Celebrity Women Who Love Dating Older Men

June 4, 2014  |  

Aaliyah sang “age ain’t nothing but a number” and these celebrity women took it to heart by falling for men much, much older than them.

Dating Older Men

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Kimora Lee Simmons

Some people have a preference when it comes to picking a mate and Kimora Lee Simmons is certainly one of them. The Baby Phat founder married into hip-hop royalty by tying the knot with Russell Simmons in 1998. Eleven years and two children later, she and Simmons, who’s almost two decades older than the long-legged model, divorced. Soon she moved on to Djimon Hounsou, who’s only a mere 14 years older than her. But after five years and a son together, they split up and she moved on to investment banker Tim Leissner whom you can tell has at least a few years on Kimmie.

"Hayden Panettiere pf"

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Hayden Panettiere

Hayden Panattiere’s first big role was on a soap opera but she grabbed Tinsel Town’s attention as the indestructible cheerleader on the hit show “Heroes.” She also found herself in love with her co-star Milo Ventimiglia. Their relationship sparked a controversy because she was just 17 at the time while he was almost 30. When that relationship went sour, she found love again with heavyweight boxer Wladimir Klitschko, who was even older than Ventimiglia by a couple years. They split up but found their way back to each other and the 24-year-old “Nashville” star announced earlier this month that she’s pregnant with their first child together.

"Padma Lakshmi pf"

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Padma Lakshmi

Cookbook author and television host Padma Lakshmi was born in India but shuttled between her grandparents in her homeland and her mother in New York. At the age of 30, she married famous novelist Salman Rushdie, a man 23 years her senior. Although he dedicated a novel to her and even based one of the central characters after her, the couple divorced three years later. Eventually she was able to find love again with financier Theodore Fortsmann. They remained together until he passed away from brain cancer in 2011 at the age of 71; she’s now rumored to be dating Richard Gere.

"Mary Kate Olsen pf"

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Mary Kate Olsen

Mary Kate and Ashley Olsen grew up in the public eye. After snagging a role they shared on the 80’s sitcom “Full House” when they were barely able to talk, the twins stayed employed in the entertainment industry. As they got older, they tried their best to shield themselves from the media. Although they’re identical twins, one of them has a penchant to date older men. Mary Kate has been romantically linked to Olivier Sarkozy, a man almost 20 years her senior since 2012. Several months ago, it was announced that the couple was engaged.

"Anna Paquin pf"

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Anna Paquin

Anna Paquin landed the job of her career when she was cast as Sooky Stackhouse in HBO’s “True Blood.” On the show Bill Compton and Eric Northman fought for her love. But in real life Steven Moyer, the actor who plays Compton, had no competition. The duo hooked up when she was 28 and he was 40. They tied the knot in 2010 and are parents to a set of twins.

"Beyonce pf"

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Beyoncé

Jay Z acts younger than his age so it’s easy to forget that he’s actually 12 years older than his wife Beyoncé. The duo first collaborated in the studio together and soon their working relationship blossomed into much more. The couple did their best to keep their relationship outside of the media but eventually word got out that one of the hottest rappers in the game was dating an international superstar. Jay and Bey recently celebrated their sixth anniversary last month.

"catherine zeta jones pf"

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Catherine Zeta-Jones

Catherine Zeta Jones and Michael Douglas found happiness with each other, establishing the quintessential May-December romance, Although he’s 25 years older than her, the two married in a lavish ceremony just weeks after Douglas’s previous divorce was finalized and the two remained by each other’s sides through his battle with throat cancer and through her struggle with bipolar disorder. Last simmer it was reported that the duo had split up and Zeta-Jones moved out of their marital home. Working through their issues, they have reconciled and are now living together again.

"Celine Dion pf"

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Celine Dion

There’s nothing like having a partner believe in your dream. Celine Dion’s manager Rene Angelil had so much faith in the Canadian singer that he famously mortgaged his house to bankroll her debut album. Never mind that she was a teenager and he was 26 years her senior. The gamble certainly paid off. Along with having an illustrious career, Dion has been married to Angelil for almost 20 years and they have three children together.

"Heidi Klum pf"

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Heidi Klum

Singer Seal has certainly dated his fair share of models. But when he hooked up with supermodel Heidi Klum he was smitten. So smitten that he made the “Project Runway” host and judge his wife even though he’s 12 years older than her . The couple renewed their vows every year for seven years until they announced they were calling it quits in 2012. Klum was also in a long-term relationship with a man who was 23 years older than her before she married Seal.

"Katie Holmes pf"

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Katie Holmes

Who could ever forget when Tom Cruise famously jumped up and down on Oprah’s sofa because he was so in love with Katie Holmes? Too bad that excitement and joy couldn’t stand the test of time. Holmes, who is 16 years younger than her mate, tied the knot to Cruise inside of a 15th century castle in Italy soon after giving birth to their first child. But six years later, she announced they were splitting up. In one of the quickest divorces in Hollywood history, the couple made their split official a mere 10 days after her announcement.

"Tina Fey pf"

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Tina Fey

As Liz Lemon on “30 Rock,” Tina Fey continuously made joke after joke that she couldn’t land or keep a man. But in real life Fey was quite the opposite from Lemon. The “SNL” alum fell in love with and married director and producer Jeff Richmond, who is older than Fey by more than a decade, in 2001. Thirteen years later, the couple is still going strong and they have two daughters together.

"Evan Rachel Wood pf"

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Evan Rachel Wood

The heart wants what the heart wants. In the case of Rachel Evans Wood, she may look innocent and angelic but her wild side fell in love with Marilyn Manson even though the rocker is nearly 20 years her senior. They started dating back in 2007 and broke up a couple times before Manson popped the big question. Even though they probably thought their relationship would stand the test of time, they called it quits for good in 2010.

"Angelina Jolie pf"

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Angelina Jolie

Angelina Jolie caught a lot of flack when word got out that she was romantically involved with her fellow Mr. & Mrs. Smith co-star Brad Pitt, a man 12 years her senior. Many blamed her for breaking up his marriage to his first wife Jennifer Aniston. The couple stayed out of the public eye for much of the beginning until the heat died down. Before Pitt, Jolie was married to fellow actor Billy. Bob Thornton, who’s 20 years older than her.

"Megan Fox pf"

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Megan Fox

Talk about barely legal! Megan Fox had millions of teenaged boys and men drooling over her in Transformers. But Brian Austin Green has been with Fox since she was 18 and he was in his 30’s. Although they broke up a couple times, they eventfully got it together and tied the knot. Fox has been very vocal about her disinterest in dating men close to her age. “Boys in their twenties are a waste of time,” she said. “They have nothing to offer conversationally; they’re immature.”

"Mena Suvari pf"

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Mena Suvari

In American Beauty, Kevin Spacey was tempted by Mena Suvari’s character even though she was a friend of his teenaged daughter. In real life, Suvari had one thing in common with the character she played. When she was 21 years old, she married cinematographer Richard Brinkmann, a man 17 years older than her. They split up five years later.

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  • Kath

    Yes, get that dough.

  • BeautyQueen

    As a young women, i’m always cautious about dating older men. Especially when i look like a teenager to them. A lot of older men will date young women just to feel young again, then when you start aging, they want to “replace” you with someone younger. And some do it just to control these young women. Been there, done that with them thinking they can control me. I ended it with the quickness, and they knew i could see right through their act. I’m not that into dating men my age either, cause most of these Peter Pans ain’t ready.

    • Virgilia Coriolanus

      Yeah–I’d say go for it as long as the guy hasn’t dated other women who are many years younger. The point is for you to be the exception, not the rule.

  • singlelady

    I have always preferred dating older men, and men closer to my own age. I did notice a big difference, but that depends on the man. Now that I’m single & 40+ I don’t think I *want someone over 10yrs older.

    • patricia

      Unfortunately the men continue to want someone younger and younger whatever their own age or appearance.

  • MuscleMansWoman

    No shade, but I wouldn’t use the term “dating” in reference to women who has married only one older man, and have remained married to that older man to this date.

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