15 Famous Cougars Dating Younger Men

You may not believe it, but statistics show that the number of older female celebs who are or have been at some point in age-gap relationships is rapidly growing. Just a couple of decades ago, in Western culture, it was still more acceptable for a man to be dating a younger woman than vice versa. But the pancake flipped, so to say, and nowadays girls have gained the upper hand in the dating business. If is good enough for Madonna, they think, then it really must be something worth trying. To the modern woman, especially the one who’s successful and financially independent, having a relationship with someone older or of similar age is not a priority. 

Actually, women do not necessarily go hunting for younger prey on purpose. For many, things just turn out that way. These ladies feel more than comfortable in the arms of their twenty-something-year-old beaus. They all have a breathtaking smile, a pleasing-to-the-eye upper body, and, needless to say, enviable stamina in bed! The 50-year-old director of Fifty shades of Grey, Sam Taylor-Johnson, initially kept her relationship with 23-year younger Aaron a secret, but when things got serious, she came forward, and said, “People in love don’t see gender, colour or religion. Or age. It’s about the other person, the one that you love and who loves you.”

Check out our list of 15 celebrity ladies who, just like Sam Taylor-Johnson, have experienced the ‘Mrs. Robinson’ effect. 

JLo and Casper Smart – 17-Year Age Gap

The two met in 2011, and it wasn’t exactly love at first sight. For either of them. 

They kept the relationship low-key at first, but then Jenny-from-the block thought there was nothing wrong in bragging about her new lover. So, the backup dancer began popping up at all sorts of red-carpet events together with the then 42-year-old star. What drew her to him? After her separation from Marc Anthony, Lopez was upset  and felt tired and old. With Casper, she came alive again. Three marriages later, the superstar still seemed very much open to the idea of exchanging vows with a new partner. A confidante even revealed that she wanted to be with Casper forever.  But five years later, they are not an item anymore. Rumor has it the couple ended it because he went on boys. 

Kris Jenner and Corey Gamble – 25-Year Age Gap

This lady’s love story with road manager Corey Gamble shows that her children’s messed-up relationships are not the only ones making the headlines in the tabloids. There was a certain Justin Bieber connection in the beginning of their relationship back in 2015. Gamble works  with Bieber’s longtime manager and mentor, Scooter Braun, and Bieber himself has been a family friend of the Kardashian-Jenner clan like…forever. Logically, Gamble and Jenner had been running  in similar circles for quite some time before they hooked up. 

In March 2017, the 61-year-old Jenner declared she had called it quits with the 33-year-old boy toy. The reason? Nobody really knows what it was, but there have been speculations that the celebrity mom felt “humiliated” over Kourtney Kardashian’s close relationship with her Corey. 

Sharon Stone and Martin Mica – 27-Year Gap

Which living woman on the face of this planet would say “no” to dating a model? Exactly, NO ONE! For a whole year, the iconic actress Sharon Stone was melting in the arms of the beautiful Argentine model Martin Mica. We can’t blame Mica for chasing after glory or money here. Oh no! With her everlasting good looks and slim figure, Stone resembles a woman half her age (which, at the time when the two started dating in 2012, was 53!). The paparazzi pictures showing them intimately making out on beaches and during fashion shows were persuasive enough to convince everybody this was true love. However, only a year after they hooked up, Stone was single again. “It wasn’t so much the age difference,“ close friends of the actress revealed. “They just weren’t into the same things. Her passions are politics, activism, and alike, and as for Martin, he is not interested in any of those.”

Susan Sarandon and  n – 31-Year Age Gap

This talented lady is not new to the Hollywood Cougar Club. Shortly after splitting from actor and father of her son Jack, Tim Robbins, in 2009, the now 71-year-old actress started dating Jonathan Bricklin, the SpiN New York co-founder. They met while on a road trip through Chile in 2010. Although the couple tried real hard to keep their relationship as private as possible, they still received a lot of attention, mostly because of the age difference of 31 years. Eventually, the couple surrendered to the mass media curiosity, and agreed to appear on the new Morgan Spurlock’s series, Connected. That was an experience which Bricklin described as “a psychotherapy with video.”

They separated in the beginning of 2015, and although Bricklin claimed he was devastated, it didn’t take long before he started dating a 64-year old, who, reportedly, had invested in his ping-pong lounge business.

Ellen Barking  and Sam Levinson – 31-Year Age Gap

The sexy blonde launched her career in Barry Levinson’s 1982 film Diner.  The director’s son Sam was born three years later. Some find it ironic that another 26 years later, the actress started dating him. No, not Barry. The son! When their relationship became news in the early summer of 2011, the two had already been living together for two years! In an interview from November the same year, Barkin claimed this was not just a fling. “I will part ways with him  when they roll me  out in a wheelchair,” she said back then. Well, she wasn’t in a wheelchair when the intense romance ended in that same year, 2011. Currently, Barkin is dating Ben Emmerson, a British lawyer. He may not be in his prime, but is still 10 years younger than the 63-year old actress.  

Cher and Tim Medvetz – 24-Year Age Gap

She is a veteran! After splitting from ex-hubby Sonny Bono (who was 11 years older  than her), the iconic singer dated more than ten younger men. Our special attention, however, goes to former Hell’s Angels biker Tim Medvetz, whom she dated in 2012. There were even rumors that Cher intended to tie the knot for the third time. Back then, Cher was 66, and Tim – 42. The plan was to hop on the back of a chopper and take off on a road trip  that would end in Las Vegas (where else!). Actually, it was Cher’s two children, Chaz and Elijah, who had been persuading her to take the plunge, saying, “Mom, get a life! Go marry Tim!” Well, apparently, nothing of the kind happened, and officially, Cher has been married only twice. So far…

Demi Moore and Sean Friday –  24-Year Age Gap

Show us a person who hasn’t heard about the drama story of Demi Moore’s tumultuous relationship with Ashton Kutcher, and we will show you exactly where Santa lives! After their divorce was finalized in December, 2013, Moore cried a river that could have drowned the whole world. But it didn’t take long before she miraculously recovered from the emotional breakdown. The reason? She started seeing Sean Friday, a drummer in the band Dead Sara. She was 51, and he was 27. They would often be spotted exchanging passionate kisses in bars, on the beach, at parties… It seamed so real, and so everlasting! But then Sean dumped her. The evil tongues claim he did it for the same reasons Ashton did – the guy wanted to have kids. 

Linda Hogan and Charlie Hill –  29-Year Age Gap

Hulk Hogan’s ex started dating 19-year old Charlie when she was 48. They got engaged in July of 2010, but never made it to the altar. They mutually decided to end their relationship two years later. But the break-up didn’t put an end to their financial relations. It appeared that Linda was not exactly the nicest sugar mama because in 2014, Hill initiated a law suit against her. The blond toy boy filed a claim for $1.5 million, citing the heavy menial labor Hogan made him do during their four-year relationship. He accused the reality star of making him fertilize 25 acres of avocado trees, digging a creek (!), waxing the yacht, pulling the reeds from the lake, and so on. However, Linda didn’t hesitate to fire back. Her lawyer filed a lawsuit against Charlie on the grounds that he had broken the confidentiality agreement. 

Currently, Linda Hogan is single. So, guys, if you want to dig a creek, or wax something, be her guest!

Ivana Trump and Rossano Rubicondi – 23-Year Age Gap

By looking at these sweethearts you get this slight feeling of dizziness that is usually associated with too high sugar levels… and a lot of early 1990’s foaming TV soaps. After divorcing Donald Trump in 1992, Ivana Trump has remarried twice. In 2008, the ex Missus, then 59, tied the knot with the then aspiring 36-year-old singer Rossano Rubicondi. The $3 million wedding was hosted by Donald Trump at his Mar-a-Lago estate, and daughter Ivanka was her mom’s maid of honor. Less than eights months later, Ivana made an official announcement she had filed a legal separation agreement. 

Kids, this a really good example that we should think not twice, but three and even more times before we do something really stupid!

Kathy Griffin and Randy Brick –  18-Year Age Gap

The year is 2013. She is the two-time Emmy and Grammy award-winning comedian Kathy Griffin (then 51), and he is Randy Brick (33), marketing executive. Unlike many others in the same age-gap relationship situation, these two have gone against all odds and are still together. She now admits that back then, she thought Randy wasn’t but a one-night stand. And yet, they’ve been together for five years now, and still no regrets.  

“Here is the thing, I don’t want a iota of judgement from you because he’s a little younger  than I am, “ the comedian said in an interview with People. “We’ve been together five years now, and we have a great time, and he is sweet and very mellow. He is a regular guy.  He’s not like a Hollywood guy.”

OK, OK, Kathy, we heard you the first time!

Vivica A. Fox and Omar “Slim” White – 19-Year Age Gap

In 2011, the then 46-year-old actress, who, ironically enough, starred in the reality show The Cougar, received an eight-karat diamond ring from her 27-year-old beau, the Atlanta Club promoter Omar “Slim” White. Vivica revealed she had never been that happy before, and they were both eager to start their life together as a family. However, uncertainty and jealousy soon cast a cloud over the couple’s happiness. Only three months after the engagement, Fox called it quits. The explanation White came out with is certainly to be remembered. He said, “She’s a good woman. It’s just one of those situations where in life , people outgrow each other.I am highly intelligent , very wise, and one thing I hate is negativity and drama. As in every relationship, tension built up, and I finally had to walk away.” 

Omar, you’ve done the first step, fine, but get yourself prepared for what may follow. Because it can get even uglier if your next girl is as highly intelligent as you are. 

Madonna and Timor Steffens – 29-Year Age Gap

The beautiful Dutch choreographer is just one of the many boy toys the infamous Material Girl has dated through the years. FYI, her previous boyfriend was 25-year-old dancer Brahim Zaibat, whom she dated briefly in 2010. Madonna and the charming Dutch Steffens were first spotted together in public in January 2014. But days before her 56th birthday and right in the middle of their European vacation, Madonna split from Steffens. She asked him to pack his bags and beat it. Sources close to the star claimed she didn’t take men like Timor seriously. Sources seem to know her pretty well, because she traded in poor Steffens for the 26-year old Aboubakar Soumahoro.

Madonna and Kevin Sampaio – 27-Year Age Gap

After ditching the 26-year-old model with razor-sharp cheekbones and rock-hard abs Aboubakar Soumahoro in the summer of 2017, the world’s most notorious Material Girl embarked on a new amorous adventure with a new male model.This time, the object of her interest was the 31-year-old Kevin Sampaio. The guy is believed to have won her respect and trust by keeping their relationship quiet. What must have really impressed Madonna was the fact that Sampaio didn’t just go running to the press after kissing her for the first time. Shortly after they became official, she took her new lover on  a romantic vacation in Lisbon. But what happens next… We have to wait and see. But we all keep our fingers crossed for Kevin to last longer than the bubbles in Madonna’s soda drink!

Robin Wright  and Ben Foster – 15-Year Age Gap

In 2010, the Golden Globe Award winning actress ditched her hyphenated last name along with the husband it came along with – Sean Penn. Two years later, she started dating actor Ben Foster, and their engagement was announced two years later. However, things between the two went in the wrong direction, and they called it off in November the same year. But then, surprise, surprise! They reunited in January 2015. You are probably guessing right where this is going. And  are right. In August, 2015, the couple announced they were ending their second engagement. Well, it’s a shame they didn’t make it to the lucky number three!

Allison Janney and Philip Joncas – 20-Year Age Gap

This year’s Gold Globe winner for Best Supporting Actress in a Motion Picture, Allison Janney (57) has been dating her boyfriend, the production supervision Philip Joncas,  since 2012. The couple met when they worked together on Way, Way Back. Beside his producing pursuits, Joncas has shown an artistic side, too. He collects paintings and photographs. It is exactly the love of art that the two have most in common. They made their red carpet debut as a couple in 2015. Although Janney had mentioned on various occasion she didn’t believe in the marriage institution, she proudly flaunted  a large engagement diamond ring on her finger during the Emmy Awards Ceremony last year.  So, what’s next for the 58-year-old actress? An Oscar, wedding bells, or… both?

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