Hollywood is no stranger to older men dating younger women, but it’s only in recent years that the term “Cougar” made its way into our vocabulary. While men seem to get better looking and more desirable with age, women have often been overlooked in the entertainment industry as soon as the appearance of the first signs of aging. No longer getting the lead role in films, it seemed like Hollywood’s double standard for female actors was something that would never change.
However, there have been a few celebrities that refused to go the way of the Dodo bird when they started to stretch beyond their peak years. Rather than submitting to the standards put forth by society, they chose to make their own rules as to what was acceptable behavior for a woman of a particular age.
While many thought of a woman dating a younger man as a small triumph for the entire sex, not all of these relationships ended with a “happily ever after.” Just as there are younger women being burned by older men, the same can be true for those that have gone the “Cougar” route. While an older woman dating a younger man should presumably exude the confidence of having the upper hand in the relationship, there have definitely been some famous women that haven’t exactly come out on top. Check out our list of 15 celebrity cougars that got burned, and see how it’s not always a good idea for a woman to date a younger man.
14 Courteney Cox
When Courteney Cox married David Arquette, fans thought it was an interesting match, even though they witnessed the chemistry between the pair in the Scream film series. With him being seven years her junior, audiences wondered what the real appeal was in this seemingly odd couple relationship. While she exuded the quirky Monica character on Friends, she offered more sophistication off-screen, which completely differed from the over-the-top personality offered by David Arquette. The public quickly came to accept their marriage, and were quite shocked once it came to an end after eleven years. While the world thought David Arquette would be the one to have difficulty moving on, Courteney seemed to be the one that got burned after the demise of their marriage. Not only has he moved on to start a completely new family, but Courteney’s new relationship has made headlines for its on-again off-again status.
13 Gabrielle Union
When Gabrielle Union and Dwyane Wade became an official item, people looked at them like they were a well-suited couple, regardless of the fact that he was nine years her junior. As a beautiful and successful actress, she seemed to be the best match to his sports celebrity. However, their relationship wasn’t always filled with romance and stability, which became evident when they took a break from their relationship. Instead of taking that time to do some self reflection and grow as a person, Dwyane Wade infamously made a “Break baby” during their time apart. Gabrielle ultimately got back together with Dwyane and they went on to marry, but the fact that she was burned during their time apart still seems to stay on the forefront of her mind. In an interview with People magazine in June 2015, Gabrielle conveniently left out the child Dwyane fathered during their time apart, and only referenced his other children and nephew.
12 Kate Hudson
Nick Jonas has famously made comments about all his celebrity crushes, including Besties Amy Schumer and Jennifer Lawrence. However, it was the comments he made about crushing on Kate Hudson after seeing her in the film, Almost Famous, that must have caught the eye of this leading lady. The two became romantically linked after numerous photos came out showing the pair on different dates, with Kate Hudson donning a much younger look – including a racy, sheer top on one infamous outing. With the actress fourteen years older than Nick Jonas, women looked at this relationship with hopeful eyes since he had expressed such fascination with the actress prior to their dating. However, the relationship didn’t last long, and he was quickly linked with other women (closer to his own age). Rather than appearing as a sexy woman still able to gain the attention of younger men, Kate became a cautionary tale as just another notch on Nick’s bedpost.
11 Kaley Cuoco
When Kaley Cuoco married the younger Ryan Sweeting, fans of The Big Bang Theory star had a few reservations about the engagement. The fact that they only dated for six months before saying, “I do” definitely raised a few eyebrows. Yet, when pictures of the wedding showed Kaley glowing in a beautiful pink wedding gown, fans tried to keep an open mind. However, things didn’t stay picture perfect for long, and the pair ended up divorcing after less than two years of marriage. Although Kaley had a prenup in place prior to the wedding, she wound up battling Ryan in court after he requested spousal support. While it’s typically a given when a younger woman requests spousal support when divorcing her older husband, it is a definite burn when it’s reversed.
10 Diane Lane
Diane Lane is an actress that seems to be exempt from the stereotype in Hollywood that forbids women of a certain age to be portrayed as sexy. Starring in films like Under the Tuscan Sun and Unfaithful, she has broken barriers in Hollywood for what age a woman can still be considered desirable. Translating into her personal life, she married the younger actor, Josh Brolin, and fans thought they were a perfectly matched couple. With Diane Lane known for her sex appeal, who better than her to make the sexy No Country For Old Men star settle down. However, the marriage was filled with numerous ups and downs, including a domestic battery arrest in 2004 and swirling cheating rumors that ultimately led to divorce. There were numerous cheating rumors throughout the marriage, including an incident with a woman at a bar in New Orleans and a leaked picture of Brolin kissing his married costar, Marley Shelton. Rather than looking at Diane Lane as a female hero, audiences started to think she was just another woman who got burned by a younger man.
9 Susan Sarandon
When Susan Sarandon married a man twelve years her junior, she instantly became a fascination for those in Hollywood. Tim Robbins might be best known for his starring role in Shawshank Redemption, but he is also known for his baby face looks and youthful energy. However, after twenty-three years of marriage, the couple announced a split. Tim Robbins ended up giving an interview with The Telegraph where he mentioned going through some struggles, which he referred to as a “midlife crisis” where he started to reevaluate his life. While fans thought Susan Sarandon had finally found the key to holding down a younger man, the split proved that even a younger man can go through a “midlife crisis.”
8 Heather Locklear
Heather Locklear is no stranger to heartbreak, since her divorce with Richie Sambora resulted in nasty tabloid headlines that brought to light the inappropriate relationship he was having with her then-best friend, Denise Richards. For a woman that has been through that kind of heartache, it’s no wonder she would choose to go a different route in her dating life. Rather than choosing an older man, she became romantically linked with the younger David Spade. In the wake of her divorce, it seemed like this was a match that would bring some fun and spontaneity to her life. Instead, it was coined as a “rebound hookup” for David Spade, who is known for his long list of beautiful celebrity romances. So, Heather Locklear looks like just another name on his list, which includes Playboy Playmate, Jillian Grace, who gave birth to his illegitimate baby girl.
8. Linda Hogan
When Linda Hogan was first introduced to audiences through the reality show, Hogan Knows Best, she didn’t exactly come off as a super likeable character. The show tended to lean towards Hulk being the love-starved husband, while she was portrayed as cold and frigid. However, once cheating rumors began to swirl and the infamous sex tape of Hulk Hogan having sex with his friend's wife during his marriage to Linda was leaked, people started to look at Linda more sympathetically. Yet, public perception is a fickle thing, and Linda starting to date the nineteen-year old friend of her children was definitely the spark audiences needed to turn against her. Linda and Charlie Hill continued their relationship until he was twenty-four-years old, and the couple even got engaged. Despite Linda looking more like a fool than a cougar due to the lavish lifestyle she afforded Charlie during their relationship, the real blow came after their split. Charlie Hill actually sued her for $1.5 million, citing he wasn’t paid for the menial labour he performed during their relationship. While cleaning the yacht and digging outside in the yard might seem like just another day for an older man, younger men seem to expect to get paid.
7 Melanie Griffith
Antonio Banderas is an actor that seems to increase in sex appeal as he ages. While it seems impossible to improve upon the sexy lead actor from The Mask of Zorro and Desperado, the salt-and-pepper hair tends to add a more distinguished look. On the other hand, time wasn’t as friendly towards Melanie Griffith. Married for nearly twenty years, she may have started off as the perfect blonde counterpart to go with his sexy dark looks and accent; by the time of their divorce, fans started looking at Antonio Banderas with a nod of agreement as to why they split. Public perception has turned against Griffith in the worst way, which begs the question of who would want her at this late age. Conversely, the world roots for Antonio as to what starlet will be the new counterpart for this Puss In Boots star.
6 Chelsea Handler
The volatile on-again off-again relationship between Chelsea Handler and André Balazs may have sparked a new interest into younger men for the actress. While André Balazs was eighteen years her senior, she went a completely different route when she was romantically linked to the rapper, 50 Cent. It seemed like an odd pairing that was almost unbelievable, but women could definitely see the appeal of dating a younger man. That appeal went away once Chelsea had to compete with his younger ex-girlfriend, Ciara. Allegedly, Ciara expressed interest in getting back together with 50 Cent, which caused the two to go their separate ways.
5 Sandra Bullock
When Sandra Bullock won the 2010 Best Actress in a Motion Picture Drama at the Golden Globes, it was her acceptance speech that made people think the actress really had the right idea when she married the younger Jesse James. At the close of her acceptance speech she said, “To my husband, there’s no surprise that my work got better when I met you. Because I never knew what it felt like for someone to have my back. So, thank you.” While it seemed perfectly romantic at the time, it became a mockery of the sanctity of marriage once the public became aware of all the affairs he was having behind her back.
Madonna has never been known as the type of girl that has been drawn to an older man. On the contrary, both of her marriages have been with younger men. While her marriage to Guy Ritchie, ten years her junior, resulted in a son and an eight-year long union, the couple didn’t exactly split on good terms and they are still fighting over co-parenting their son Rocco. When details emerged regarding their split, Guy Ritchie allegedly made some comments about Madonna that were a definite burn. Saying that he would call Madonna “It,” was just a small part of how he allegedly used defamatory language against the pop star. An inside source gave a statement to the Mirror, stating, “She doesn’t understand that her refusal to grow old gracefully makes her look desperately sad. Guy just didn’t need the grief.” If it doesn’t get worse than that, then it’s unclear what a really negative comment might be against the aging pop star.
3 Vivica Fox
While some cougars get burned and then quickly learn their lesson about dating younger men, Vivica Fox seems to be a glutton for punishment. When she appeared on the red carpet with 50 Cent, people commented on her revealing dress with the same gusto given to the infamous Versace J-Lo dress. However, the talk over the dress lasted longer than the actual relationship, and the two split unceremoniously while he was already linked with a new starlet. She was also romantically linked to Robert Ri’chard, who was twenty years her junior, and also played her son in Chocolate City. In 2003, Fox was dating the twenty-four-year old Washington Redskins player Darnerien McCants, but the two split after only six months of dating. While a male celebrity linked to so many younger women would probably get the thumbs up from his peers, public perception of Vivica Fox has become negative in that she doesn’t seem able to keep a man or at least maintain the attention of a younger man.
2 Jennifer Aniston
After Jennifer Aniston and Brad Pitt divorced, audiences wanted so desperately for the star to find a true “happily ever after” like her ex seemed to do with Angelina Jolie. So, when she started dating John Mayer, nine years her junior, fans were hopeful that she would finally find happiness. At the time he started dating Jennifer Aniston in 2008, the world hadn’t yet given John Mayer the title of careless playboy that he has today. Famous for his kiss-and-tell antics, the two split after dating for only about a year. While he didn’t quite burn her as bad as Taylor Swift, who he called out for “cheap songwriting,” he did elude to Jennifer Aniston’s age when he said “I think she’s still hoping it goes back to 1998.”
1 Demi Moore
When making a list about cougars that got burned, there’s no way to leave out Demi Moore. The ultimate cougar in Hollywood, Demi Moore seemed to get even more attractive as she aged. While the fresh-faced beauty she was with the short-haired character in Ghost was already attractive, fans saw her as an ultra sexy long-haired version in films like Striptease and Charlie’s Angels: Full Throttle. When she became romantically linked to Ashton Kutcher, fifteen years her junior, she became the envy of middle-aged women everywhere. While the couple started off with a seemingly endless amount of admiration on Ashton’s part, things changed as the relationship grew longer. Toward the end of their relationship, there were a number of cheating scandals that made tabloid headlines, including a front cover US Weekly with a twenty-two-year old claiming to have had sex with Ashton while he was with Demi Moore. In a scenario where age would be a hot button issue for an older woman dating a younger man, the ultimate burn would be for him to leave for a younger woman. Yet, leave he did, and with a woman twenty-one years younger than her, no less.