Older men dating much younger women has long been accepted, though sometimes disdainfully so if the man is old enough to be the girl’s grandfather. Yet, it happens time and again. But what about relationships where the woman is old enough to be the man’s mother or, worse, grandmother?
When before it was almost unheard of, women dating much younger men has become all the rage. And nowhere is this trend becoming more rampant than in Hollywood. It doesn’t hurt that the Hollywood MILFs who snag their boy toys are successful, rich, beautiful, and of course, hot. Here’s a run-down of tinsel town’s cougars with their much younger significant others.
12 Julianne Moore and Bart Freundlich (age gap: 9 years)
Her first marriage didn’t last, which is probably why she didn’t jump right into it with her next beau, director Bart Freundlich, nine years her junior. But after a son and a daughter, Moore and Freundlich finally tied the knot and have been happily married for the past 11 years.
11 Janet Jackson and Wissam Al Mana (age gap: 9 years)
After two failed marriages, Janet Jackson decided to keep her third marriage under wraps. She wed fashion billionaire Wissam Al Mana, who is nine years younger than her, in 2012, but the couple keeps the lowest of profiles. In fact, they’re hardly seen out and about, most likely due to the fact that Al Mana guards his private life very fiercely.
10 Gabrielle Union and Dwayne Wade (age gap: 10 years)
Who would think that Gabrielle Union is already in her forties? She surely doesn’t look her age, which is why she can easily get away with being married to NBA star Dwayne Wade, who’s ten years younger than Union. The couple tied the knot in August 2014, reuniting after a brief break-up. But it looks like Union has a penchant for younger men. Her ex-husband, NFL star Chris Howard was also younger than her, although by a mere two years.
9 Paris Hilton and River Viiperi (age gap: 11 years)
She’s only in her early thirties so she’s technically far from being a cougar. But since Paris Hilton dated a man 11 years her junior, she can unofficially be considered one. The 33-year-old heiress dated Spanish model River Viiperi for two years and though no one suspected that there was trouble in paradise, new photos surfaced in late July 2014 of Hilton smooching with a new guy in Malibu Beach, followed by some cryptic Instagram posts from Viiperi, hinting at a break-up.
8 Mariah Carey and Nick Cannon (age gap: 11 years)
Though they’ve recently separated, many were surprised that Mariah Carey’s marriage to Nick Cannon lasted longer than it did. With an 11-year age gap, it was one of the most unlikely pairings in Hollywood. But they defied the odds, got engaged, married, and had two beautiful children. When everyone thought it was going to last, the couple announced their separation in August 2014.
7 Courteney Cox and Johnny McDaid (age gap: 13 years)
While we all thought Courteney Cox and ex-husband, David Arquette’s age gap was pretty big at eight years, it seems like she really intends to stay true to her character in her TV show, Cougar Town. Cox began dating Snow Patrol guitarist Johnny McDaid, 13 years her junior, late in 2013 and the happy couple recently announced their engagement. McDaid seems to get along with Cox’s daughter too, so hopefully this marriage can last!
6 Robin Wright and Ben Foster (age gap: 14 years)
She had a very high-profile marriage to Sean Penn, whom she was married to for a good 14 years. And while that’s a veritable record by Hollywood standards, it didn’t last. After the divorce, Robin Wright dropped Penn from her screen name and reverted back to her original name when she was single. The House of Cards star began dating actor Ben Foster, 14 years her junior, in 2012 and they happily announced their engagement in January 2014.
5 Demi Moore and Ashton Kutcher (age gap: 16 years)
Perhaps the most publicized cougar in Hollywood, Demi Moore married Ashton Kutcher, who is 16 years younger than the beautiful actress. It seemed like a great pairing at first. Moore’s three daughters fully accepted Kutcher as their stepfather and Moore’s ex-husband Bruce Willis even walked her down the aisle. But after eight years of marriage, the pair split and it was allegedly a bad break-up.
4 Jennifer Lopez and Casper Smart (age gap: 18 years)
She has often been compared to Elizabeth Taylor, not because of her talent or beauty, but because of her many failed relationships. Jennifer Lopez has been married three times and has been engaged at least once, but she’s currently single, from what we know. But up until a few months ago, she was dating her back-up dancer Casper Smart, who’s 18 years her junior. Despite the odds, the pair dated for three whole years—a certified long-term relationship.
3 Madonna and Timor Steffens (age gap: 29 years)
The material girl seems to love boy toys because she’s almost always dated men who were younger than her. The two men who fathered her children are years younger and there’s an even bigger age gap with her last two relationships. Madonna dated her back-up dancer, who’s 30 years younger than her and she’s currently dating choreographer/dancer Timor Steffens, who’s only slightly older than her ex. Steffens is 29 years Madonna’s junior.
2 Sharon Stone and Martin Mica (age gap: 30 years)
At 56, Sharon Stone oozes more sexuality than an average 25-year-old with a supple body and pretty face. And not only does she appeal to male audiences of all ages—it seems she prefers dating in the younger age group as well. Stone was once romantically linked to Christian Slater who was 10 years her junior. But if that wasn’t eyebrow-raising enough, she’s currently in an on/off relationship with Martin Mica, an Argentinian model who’s 29 years younger than the sultry actress.
1 Susan Sarandon and Jonathan Bricklin (age gap: 31 years)
After a failed marriage and broken long-term relationships with men who were more or less in her age range, Susan Sarandon probably decided to date men from another generation. Her longest relationship was with Tim Robbins, whom she lived with for 21 years, giving her two sons. Her current boyfriend is her business partner Jonathan Bricklin, who’s—wait for it—31 years her junior. They’ve been dating for almost a year, so let’s see if this one’s for keeps.