40 of Your Favorite Celebrities Who Just Love Those Younger Women

Sly Stallone and Jennifer Flavin (30 years)

While most actors go through their lives getting the occasional big role here and there, Sly Stallone has both written, and starred in some of the most iconic movies in history, including the Rocky and Rambo franchises, along with more cult-like flicks like Nighthawks, Cobra, and Demolition Man. And being a megastar the likes of Stallone, allows for the opportunities to date some very attractive young ladies, including one Jennifer Flavin, a woman 30 years his junior. The two have been married to since 1997, sharing three daughters together.

Diddy and Lori Harvey (28 years)

Affectionately known as P. Diddy, or Puff Daddy, or just Diddy, Sean Combs is one of the most successful and talented entrepreneurs to come out of the mean streets of New York City. Getting his start as a rapper in the early 90’s. P. Diddy was able to parlay his early popularity into a career as one of the most successful record producers of his generation, making him both famous and incredibly wealthy, and with fame and wealth come the ladies, and Diddy has had his fair share, including the much younger Lori Harvey.

Tom Cruise and Katie Holmes (16 years)

Tom Cruise has been a megastar for decades with a list of hit movies too long to name here. Tom has also been a notorious ladies’ man, dating some of the most beautiful women in the world. But Tom is a bit different that others here as he likes to be with other accomplished actors such as Kim Bassinger, Mimi Rogers, and Katie Holmes, who was 16 years his junior. While Katie and Tom are no longer a couple, they do share children together and have a very amicable relationship.

Jason Statham and Rosie Huntington-Whiteley (20 Years)

Jason Statham went from being an underrated actor in British cinema, to one of the top action heroes in Hollywood. In addition to his successful acting career, Statham is also an accomplished martial artist, a combination that has allowed him to snag some very fine ladies over the years, including a tall and statuesque blond and Victoria Secret model by the name of Rosie Huntington-Whiteley. Even though they are separated by a 20-year age gap, the couple have remained together since 2010 and share two children.

Harrison Ford and Calista Flockhart (22 Years)

When Harrison Ford and Calista Flockhart first became an item back in 2002, he was on top of the world as a legendary actor, famous for some of the most iconic movie roles in history, and she was a much younger, out of nowhere actor in a sitcom. The pairing seemed odd to say the least, and many predicted that the couple wouldn’t last through Christmas of that year. Well, the Ford/Flockhart union not only made it past that Christmas, they continue on to this day, some 20 plus years later.

Lionel Richie and Lisa Parigi (40 Years)

There is not another singer on this list that is more iconic than Lionel Richie. This man has enjoyed an unprecedented career and is widely recognized for his endless string of romantic ballads. And of course, the women love them some romantic ballads, which has enabled Mr. Richie to score many a young lady over the years, maybe none as young as his current armpiece, Lisa Parigi, a model who is a whopping 40 years his junior.

Randy Jackson and Simone (35 Years)

While the general public knows Randy Jackson as one of the panel judges on the smash hit show, American Idol, Jackson actually got his start as a jazz fusion and rock bass player, where he enjoyed incredible success for many years. The combination of his accomplishments as both a musician and American Idol judge has allowed him to snag the very attractive, singer/songwriter, Simone who also happens to be just shy of 4 decades younger than Jackson.

Bruce Willis and Emma Heming (24 years)

Besides being recognized as one of the great action stars of the last thirty years, Bruce Willis is Hollywood royalty. The actor also shared nuptials with another famous actor in Demi Moore. The couple were married for 13 years and produced several children who themselves have become famous in their own right. And even though the couple are no longer an item, they have not only remained friends, but the whole family is often together on the regular. In 2009, Willis married a much younger actor named Emma Heming, and the couple share two children together.

Al Pacino and Meital Dohan (39 Years)

Coming in as that second largest age gap on our list is the couple of Al Pacino and Israeli actress Meital Dohan. The two met in usual Hollywood fashion at an after party for a show screening. Dohan states that, at first, she kept the relationship a secret from her parents due to the age gap, but Pacino being Pacino, she went ahead anyway. But the whole thing fell apart two years later with Dohan citing the almost 40-year difference, saying she wanted to make it work, but Pacino is really just an “elderly” man at this point.

Ben Affleck and Ana de Armas (16 Years)

Ben Affleck has a notorious reputation as a ladies’ man. He’s dated the whose who in the world of Hollywood and entertainment, from Gwyneth Paltrow to Jennifer Garner to Jennifer Lopez and beyond with most of them sharing the same age range, but it seems that Anna de Armas changed all of that when they first hooked up after filming the movie Deep Water. Affleck and the brunette beauty exploded into a whirlwind romance on the quick and, as Hollywood people tend to do, professed their instant love for each other, regardless of their 16-year age gap.

Jeff Goldblum and Emilie Livingston (30 Years)

If you’re a Gen X’r, you will know Jeff Goldblum from any number of box office hits including The Fly, Jurassic Park, and Independence Day. If you are a millennial, you might recognize Jeff Goldblum for his recent, quirky appearances in television commercials. Mr. Goldblum was also one half of a Hollywood power couple for years as the husband of another Hollywood royal, Jeana Davis. These days, Mr. Goldblum has been bitten by the “younger woman bug” and hooked up with Emelia Livingston, some three decades his junior.

Richard Gere and Alejandra Silva (34 Years)

Richard Gere has not only been one of Hollywood’s most popular leading men, he’s also a been the target of woman the world over, looking for an opening so that they can get their hands on the handsome megastar. In comes a Spanish beauty, Alejandra Silva. At 34 years of age, she is young enough to be Gere’s granddaughter, yet she was able to swoop in and grab up the legend, who, it turns out, was a long-time family friend.

Dane Cook and Kelsi Taylor (26 Years)

Dane Cook, the popular stand-up comedian who makes his living by making people laugh, had to act quickly to make sure that he wouldn’t become the laughing stock of his critics for marrying a Pilates instructor, 26 years his junior. He and his future bride did so by joking on each other about their age gap to diffuse things with Cook hoping that he’ll be able to hold his young children while on his deathbed, while Taylor quips about the importance of having kids while young.

David Hasselhoff & Hayley Roberts (28 years)

Things have got to be a bit uncomfortable when your new bride is only nine years older than your daughter, but that is exactly where former Baywatch star, David Hasselhoff, finds himself after tying the knot with a the much younger, autograph seeking Welsh model, Haley Roberts. Yes, the two met when the 39-year-old Roberts tracked down the 67-year-old actor at his hotel, looking for an autograph for which Hasselhoff wanted her phone number in exchange. The two have been together ever since.

Heidi Klum & Tom Kaulitz (17 years)

Now, we are all for gender equality, and seeing as how this list is dominated by older men with younger women, we had to toss in an older woman to provide some balance which leads us to the near 50 year old supermodel, Heidi Klum, grabbing herself up a much younger musician from Germany, Tom Kaulitz. The two only dated for roughly a year before tying the knot in 2019 and by all accounts are a very happy couple.

Don McLean & Paris Dylan (48 years)

American Pie is one of the all-time great hits of the 1970’s. There was a minute when you couldn’t turn on your radio without hearing the catchy lyrics, and it has since found its way into historical lore and reincarnation via endless television commercials that use it to hawk their products. And writing such an iconic tune opens up your world to fame, wealth, and an array of very attractive and very young females. Introducing Paris Dylan, the 26-year-old model and regular on social media who bagged herself a legend, despite their 74-year age gap.

David Foster and Katherine McPhee (34 Years)

With a quick glance at our next couple, one might assume that famed musician, composer, and producer, responsible for writing, and producing hits for the likes of Whitney Houston and Michael Bublé, as well as composing the scores for many hit movies, just picked up a much younger armpiece to show off at parties, but Katherine McPhee is a successful singer/songwriter in her own right. Despite their 34-year age difference, the couple boast of a very happy marriage where they often work together on a variety of music projects.

Bob Saget and Kelly Rizzo (23 Years)

Bob Saget has enjoyed a very successful life as both a stand-up comedian and sitcom star. He was originally married to a woman his own age, Sherri Kramer, throughout the 80’s and 90’s until the couple split up in 1997. This left Bob a perpetual bachelor for the next 20 years until he was introduced to the much younger Kelly Rizzo through a mutual friend. Unfortunately, the couple was only able to share a brief four years together when Saget passed away suddenly in 2022.

Gavin Rossdale and Sophia Thomalla (24 Years)

Life is not always easy for an aging rockstar. You don’t sell out stadiums like you once did, and the young and sexy woman that used to show up at your hotel for a tryst have moved on to becoming worn down, soccer moms. But all is not lost for Gavin Rossdale who, at the age of 52, is still reeling em in, like the German model Sophia Thomalla, a woman half his age. However, the pair only lasted a year before she was caught making out with a famous German soccer player, leaving Gavin out in the cold.

Sean Penn and Leila George (32 Years)

In his lengthy career in Hollywood, 62-year-old Sean Penn has made the rounds with the ladies. From his often publicized, tumultuous relationship with Madonna, to his marriage and divorce from Robin Wright Penn, Sean has done just fine. And Penn has kept the streak going with Leila George, the beautiful, 30-year-old Australian actress. Unfortunately, George surprised Penn with divorce papers a year into their nuptials, with Penn admitting that the combination of alcohol, drugs, and his obsession with politics ruined their union.

Robin Thicke and April Love Geary (18 Years)

The split of Robin Thicke and his partner of 21 years, Paula Patton, was heavily publicized and traumatic for the pair, with Robin working desperately to save a marriage that was fraught with infidelity on his part. But with the divorce of a megastar singer, comes the younger ladies, and the ink wasn’t even dry on the paperwork when one April Love Geary popped into the picture to grab up the crooner. The two are happily married and share three children together.

Dolph Lundgren and Emma Krokdal (38 Years)

Dolph Lundgren is best known as the mindless Russian fighter from Rocky V, but did you know that this Swedish star has a Master’s degree in chemical engineering? But even being a highly intelligent, handsome, successful actor does not save you from the many head shakes you will receive from marrying your 24-year-old, physical trainer. Even though Krokdal is actually the same age as Lundgren’s daughter, he claims that they are a “perfect match” and they are already planning their wedding.

Michael Douglas’s and Catherine Zeta-Jones (25 years)

Both Michael Douglas and Catherine Zeta-Jones were at the top of their acting game when they began dating, but that didn’t stop the couple from receiving extensive criticism for their quarter of a century difference in age. Turns out that Douglas and Zeta-Jones have gotten the last laugh as, even though they did experience a temporary split around 2013, they reconciled and are still going strong more than 20 years later.

Billy Joel and Alexis Roderick (32 Years)

Billy Joel has never had a problem getting an attractive woman, after-all, he was married to supermodel Kristie Brinkley, and even though he has now made it into the sexagenarian age group, it’s difficult to let go of those young and successful hotties, hence his latest marriage to a 33-year-old, former Morgan Stanley executive and all-around beauty, Alexis Roderick. This is not a whirlwind romance; the couple have been together since 2009 and are expecting their first child.

Dennis Quaid and Laura Savoie (39 Years)

Is it true that the fourth time is a charm? This may be the question 68-year-old Dennis Quaid is asking himself with his recent marriage to the 39-year-old Laura Savoie. Savoie is not like the typical yoga instructor or wannabe actress, she has a Master’s degree in accounting from Notre Dame, not an easy get. And she loves Quade for his “love of life.” It will remain to be seen whether or not Quaid can make this one last, but the odds aren’t bad.

John Stamos & Caitlin McHugh (23 years)

The Fuller House star and his wife, 33, tied the knot on Feb. 3, 2018, in Studio City, California. After almost two years of dating, Stamos, 56, proposed Oct. 22, 2017, at Disneyland, one of McHugh’s favorite places. The pair first met while filming an episode of Law & Order: SVU in 2011, but it wasn’t love at first sight.

Mickey Rourke & Anastassija Makarenko (34 years)

There was a time when Micky Rourke was one of the most sought after, leading men in Hollywood, thanks to his incredibly good looks and smooth charm. But, after many years out of the limelight and in the boxing ring where Rourke would compete, both his looks and his charm were gone. However, Micky still had enough swagger to land a very young, beautiful woman Anastassija Makarenko, some three decades younger than the “Pope from Greenwich Village” actor. The two would remain a couple for six years before they split, leaving Rourke as a bachelor ever since.

Mick Jagger & Melanie Hamrick (44 years)

Besides being rock royalty, Mick Jagger just loves to have him some kids. Prior to meeting his latest conquest, 33-year-old ballerina Melanie Hamrick, the 76-year-old crooner already had seven children from previous relationships. And of course, at the ripe age of 76, Mick is a grandfather five times over. Jagger’s oldest child is roughly a decade older than his new bride, who, in 2016, gave birth to the Rolling Stones front man’s eight child, Deveraux Jagger.

Steven Tyler and Aimee Ann Preston (41 Years)

As the front man for one of the most renown rock bands in history, Aerosmith, 74-year-old Steven Tyler has been rocking arenas for decades while enjoying all the perks that one might expect of someone of his status, including dating beautiful, younger woman. In an effort to keep things consistent, Tyler hooked up with his very attractive, 35-year-old personal assistant, Aimee Ann Preston. They’ve been together as early as 2014 and appear to be going strong to this day.

Zach Braff and Florence Pugh (21 Years)

Actor and filmmaker, Zachary Israel Braff, has been a household name from his time playing J.D. on the hit television sitcom, “Scrubs” in the early 2000’s. He first met fellow actor Florence Pugh online, and the two then worked on a film together where they clicked and began dating. This led to criticism from online trolls for which Pugh responded that she was old enough to date who she wanted, regardless if that person was a quarter of a century older than she. The couple managed to make things work for three-years before calling it quits.