It takes a lot to make a relationship, whether you’re an average Joe, or a famous star who graces the stage and screen. Some relationships are based on mutual interests, which usually means you’re both in a similar age group. However, a lot of the denizens of Tinsel Town prefer to date way younger. Join us for our roundup of some of the Hall of Fame’s most active male daters, and their young lady partners.
Steven Tyler — Aimee Ann Preston (41 Year Difference)
Aerosmith frontman Steve Tyler is no stranger to the limelight, and all the attention it brings. While people are interested in him, they’re just as interested in who he’s dating.
One of his famous consorts is former assistant Amiee Ann Preston. Tyler and Preston got together even though they have a 41-year difference in age. Despite being together for a while they never officially married.
Leonardo DiCaprio — Camila Morrone (23 Year Difference)
A rare example of a child star transitioning into a successful adult actor, Leonardo DiCaprio has been in the industry a long time. This also means his love life has been followed closely and even poked fun at by voices such as Ricky Gervais.
His current relationship is with Camilla Morrone, going strong since 2017. There’s a 23 year age difference between them, but it doesn’t bother them one bit.
Al Pacino — Meital Dohan (39 Year Difference)
A veteran actor, known for Scarface, Al Pacino has been a staple of Hollywood for years. Although he enjoys his independence, he’s known for dating various famous actresses.
At the moment he’s with Meital Dohan. The two have a 39-year difference in age. That said, he has dated older women, but for now he has a spark with Ms Dohan. Say hello to his young girlfriend.
Sean Penn — Leila George (32 Year Difference)
Sean Penn has been married many times, and to some famous women like Robin Wright and Madonna. Those relationships certainly didn’t last. Now however it appears he’s aiming younger.
He ended up in a very publicized relationship with Layla George, a woman he is 32 years senior to. The two seem happy together despite the gossip. He also hasn’t acted much recently. Perhaps he’s ready to settle down.
Dennis Quaid — Laura Savoie (39 Year Difference)
Dennis Quaid hasn’t been successful in love. He’s been divorced three times. But it looks like his luck has changed. The 65-year-old has been more private in recent years, but we know he’s dating much younger now.
He’s now with Laura Savoie, whom he’s 39 years older than. After only four months he proposed and the two have since been happily married.
Tom Cruise — Katie Holmes (16 Year Difference)
A more well-known pair on this list, Top Gun star Tom Cruise and Katie Holmes are Hollywood A-Listers, whether on the big screen or small. Note that Cruise dated others before Holmes-like Nicole Kidman and Mimi Rogers.
Cruise eventually ended up with the woman 16 years his junior. It didn’t bother them. Eventually, though they broke up, but the age gap wasn’t the cause.
Pete Cook — Alba Jancou (39 Year Difference)
Pete Cook isn’t a well-known actor, instead, he’s an architect. He became famous when he married Christie Brinkley. After their split, Cook started dating women quite a lot younger than his ex.
He ended up dating Alba Jancou, who is only 21 years old. Therefore the age gap between them is 39 years! Infact, she is even younger than his daughter, but that didn’t stop their marriage. Their relationship is still strong.
Zach Braff — Florence Pugh (21 Year Difference)
Scrubs star Zach Braff has often dated women in his age group, such as Hollywood actresses Kirsten Dunst and Drew Barrymore. However after those relationships didn’t work out, he found someone younger than he is.
Even though he is 21 years older than her, Braff has been in a relationship with Florence Pugh since 2019. Pugh is known for Black Widow. Her and Braff have often justified their relationship. But they do have an obvious spark.
Michael Sheen — Anna Lundberg (25 Year Difference)
Shooting to new heights on the show Prodigal Son, Micheal Sheen has been making waves elsewhere with his love life. After splitting with Kate Beckinsale, he got together with a young lady, Anna Lundberg.
There’s a big age gap between the two, 25 years in fact. However, they’re making it work and had a healthy child together in 2019, in the month of September.
Kelsey Grammer — Kayte Walsh (25 Year Difference)
After a widely publicized breakup with Camille Grammer on the show Real Housewives of Beverly Hills, Kelsey Grammer decided to go under the radar.
After a while he met Kayte Walsh. He was 64 years old at the time, and she was a full 25 years younger than him. The sparks flew regardless and soon after the two got married. A happy ending after all.
Robin Thicke — April Love Geary (18 Year Difference)
Robin Thicke of Blurred Lines fame, or infamy, sought someone the opposite of his ex-wife, Paula Patton, after a nasty divorce. It seems he wanted someone very different to be able to move on.
Only a few short months after the divorce, he found someone new, runway model April Love Geary. Despite being 18 years apart in age, the two seemed happy together. Happy enough to have three children together so far.
Dane Cook — Kelsi Taylor (26 Year Difference)
Dane Cook is a well-loved comedian known for his edgy, abrasive and loud style and hot takes. Perhaps that’s why he went for a lady his junior. Kelsi Taylor and Cook have been dating for a long time now.
Taylor and Cook met at a football-watching party at his house, and only grew closer from there. Despite being 26 years older than her, they have a lot of mutual interests.
David Foster — Katherine McPhee (34 Year Difference)
How a couple met is always a great story to them. David Foster and Katharine McPhee met when McPhee was featured on season five of American Idol. McPhee was actually going to sing a song written by Foster. So he helped her practice. From there it was a one way trip to love.
The relationship went so well they announced they were engaged in 2018. The journalists couldn’t help by fixating on the 34-year age difference.
P. Diddy — Lori Harvey (28 Year Difference)
Puff Daddy AKA P. Diddy AKA Sean Combs is a showbiz superstar and a veteran of the industry. As such he’s no stranger to the tabloid. He counts J-Lo among a list of past relationships.
When he and J-Lo eventually split up, the entertainment titan ended up with Lori Harvey, and a 28-year age difference between them. Sadly the relationship only lasted a short three months.
Wilmer Valderrama — Demi Lovato (12 Year Difference)
Well known for playing Fez in That 70s Show, Wilmer Valderrama got together with former Disney star Demi Lovato. The two caused a buzz when they got together for a six-year relationship, and due to the vast difference in their ages.
There’s a 12 year difference between them, but they still managed to keep it smooth before peacefully parting ways. Valderrama is currently engaged to Amanda Pacheco, and they have a child.
Sylvester Stallone — Jennifer Flavin (22 Year Difference)
Sylvester Stallone of Rocky fame actually met the love of his life while shooting the series. This isn’t the first relationship on our list that started as business. They’ve been together for over 20 years now!
Stallone met his now wife Jennifer Flavin while filming Rocky V, when she was 19 and he was 42. They’ve spent a full 24 years together, that’s more than the age difference between them.
Mel Gibson — Rosalind Ross (35 Year Difference)
Mel Gibson, an acclaimed actor and director, is a controversial figure that’s either loved or hated, but still a staple of the Hollywood business. It just makes sense his love life would be as controversial. So what’s the deal?
Gibson got together with Rosalind Ross, who is 35 years his junior. This big difference could be an issue for some, but Gibson doesn’t mind one bit.
Ben Affleck — Lindsay Shookus (8 Year Difference)
Ben Affleck has been in the news lately, not just for his stellar performances as Batman, but for getting back together with J-Lo. He did take a page from Bruce Wayne’s book though, and was a playboy for a while.
During that period he dated SNL producer Lindsey Shookus, with an admittedly small age gap of either years, but that may have been an issue anyway. They split quite quickly.
Chris Pratt — Katherine Schwarzenegger (11 Year Difference)
From sitcom funnyman to full blown action star, Chris Pratt is now a leading man in Hollywood, well known for films series like Jurassic and Guardians of the Galaxy. This has also made his love life more noteworthy. After splitting with Anna Faris, he found someone new.
Despite being 11 years older than her, Pratt got with Katerine Schwarzenegger and after a time the two got married. Since then they’ve even had a child together.
Billy Joel — Alexis Roderick (32 Year Difference)
Billy Joel can count “marriage veteran” on his CV, as he’s had quite a few. Despite the first few of them not working out, he never stopped trying. After his marriages with Christie Brinkley and foodie Katie Lee concluded, he found his fourth love.
There’s a whopping 32 year age difference between them, but it seems to be working. The rockstar married Alexis Roderick in 2015, and the two have been happily married ever since.
Ben Affleck — Ana De Armas (16 Year Difference)
Yup, a repeat name on this list, it’s Ben Affleck. We did say he had a few relationships! Post-Jennifer Garner, Affleck had a few younger women on his arm before getting back together with the one, J-Lo.
One relationship of note is the one he had with Cuban actress Ana de Armas. The age gap between them was significant, being a full 16 years. Still they seemed to be happy and parted on good terms.
Scott Disick — Sofia Richie (15 Year Difference)
Scott Disick, although not too well known at first, rocketed to fame as the partner of Kourtney Karadashian of Keeping Up With the Kardashians fame. Their relationship was famed for its “On-Off” nature, but eventually they parted amicably for good.
A couple years back in 2017, Disick made public his relationship with Sofia Richie, Lionel Richie’s daughter. There’s a 15 year age gap between them. Complicating things was the fact that the Richie and Kardashian families were friends.
Alec Baldwin — Hilaria Thomas (26 Year Difference)
Perhaps the best known Baldwin bro, Alec has been a mainstay in Hollywood for decades, and had the publicizing of his love life to show for it. His relationship with Kim Basinger was noted for its tumultuous nature. After it was over the paparazzi were eager to see who he got with next.
Eventually he got together with the 26 year younger Hilaria Thomas, and the two really hit it off, eventually getting married and having four kids.
Josh Duhamel — Audra Mari (21 Year Difference)
Being constantly in the spotlight must strain a relationship. It appears this was the case when Josh Duhamel and Fergie ended their marriage after a long eight years. What, or who, was next for Duhamel?
Since splitting, Duhamel had a few relationships with women his junior, the most recent being world famous model Audra Mari, who is a whole 21 years younger than him. She also lays claim to the title of Miss World America 2016!
Harrison Ford — Calista Flockhart (22 Year Difference)
You may know him as Indiana Jones or Han Solo, but did you know he was a casanova off screen as well? Perhaps he’s finally settled down though, with Calista Flockhart.
Ford is a whole 22 years older than Calista Flockhart, but the two have been in a relationship since 2002, and have a kid together. It seems the age difference wasn’t a problem in this case. The two are often spotted together on red carpets, as happy as the day they met.
Nicolas Cage — Alice Kim (20 Year Difference)
Nic Cage, loved for his intense and sometimes whacky performances, had been married two times before meeting his third wife Alice Kim. They met at a sushi spot Kim was waitressing at and felt a spark. Eventually they tied the knot.
Unfortunately the two eventually divorced. No one knew whether it was the 20-year age difference, or because they just didn’t have enough in common. She wasn’t the last younger woman Cage would get with though.
Jeff Goldblum — Emilie Livingston (30 Year Difference)
Reddit favorite Jeff Goldblum had a few marriages in the 1980s, but wasn’t successful. The marriages ended for different reasons, and amicably enough, but Goldblum couldn’t seem to catch a break. It would be some time but there was light at the end of the tunnel.
In 2014 however, his luck changed. He met Emilie Livingston, who is 30 years his junior, but has stuck with him ever since. They have two kids together. Finally a happy ending for a much loved actor.
Bruce Willis — Emma Heming (24 Year Difference)
Demi Moore and Bruce Willis were a power couple of the 1990s, then to everyone’s shock, their marriage ended. Note though that they remained on friendly terms, but went their own ways. Willis ended up finding a new relationship.
Willis had a few relationships post-Moore, but none lasted too long. That was until he met Emma Hemming, whom he is 24 years older than. The two entered a whirlwind relationship, got married and had two kids together.
Lorenzo Lamas — Kenna Nicole Smith (27 Year Difference)
Not a well known name, Lorenzo Lamas still found fame in the TV business on shows like Falcon Crest. He went through four unsuccessful marriages, and it seemed like he was destined to be alone, before he finally got with Kenna Nicole Smith.
Lamas met Smith through his godmother and started a relationship even though there was a 27-year difference between them. Eventually they got married, and they’ve been going strong ever since.
James Woods — Sara Miller (42 Year Difference)
Old timer James Woods has obviously had a lot of time in the spotlight and with it his romantic relationships. He had two marriages that ended, and so everyone thought perhaps he was done with love.
Turns out this wasn’t the case, as he got together with Sarah Miller. There’s a 42-year difference between them, but the two are like giddy teens with each other. Rumors flew when Woods was spotted at a restaurant with the 32-year old, and a big diamond ring on her finger.
Nicolas Cage — Riko Shibata (30 Year Difference)
Another one for Nic Cage, this relationship came up after he left Alice Kim, and the age gap was even bigger this time, a whole 30 years! It became official when he made his relationship with Riko Shibata public at the Independent Spirit Awards in 2020.
Neither seem worried about the 30 year difference, in fact just a month after making it public, the two got married! The two are still together to this day.
Lionel Richie — Lisa Parigi (40 Year Difference)
We spoke about a Richie before on this list, but this time we’re talking about the main man himself! Lionel Richie is perhaps best known for his love songs, so it makes sense he’s a Valentino himself. That said, in 2014 when he started a relationship with Lisa Parigi, he kept it pretty hushed.
The relationship became unexpectedly public in 2021, when people began discussing the 40-year difference between the two. Despite the scrutiny, the two are still happily together.
Brad Pitt — Nicole Poturalski (29 Year Difference)
Following his divorce with Angelina Jolie, Brad Pitt’s love life has been under a lot of attention. With all the scrutiny you’d think Pitt might avoid relationships altogether, but that isn’t so! The paparazzi have their work cut out for them.
In 2020 Pitt got together with Nicole Poturalski. The German model is very happy with Pitt despite the large 29 year age difference between the two. They’ve been spotted together all over Tinsel Town.
Dolph Lundgren — Emma Krokdal (38 Year Difference)
This star made his big breakout as Ivan Dragnov, the Rocky villain! Since then he’s gotten consistent work in many, mainly action, films and series. He’s also quite the science buff.
Despite his fame, he’s managed to keep his relationships quite low key, until his latest one with a personal trainer from Norway named Emma Krokdal. The reason for the buzz is the 38 year age difference between the two.
Vincent Cassel — Tina Kunakey (30 Year Difference)
Vincent Cassel is a well-known actor hailing from France. Under his belt are acclaimed pieces of media such as Ocean’s 12 and Westworld. He’s particularly noted for playing strong men, but also for his interesting real love life.
He and his wife have a big 30-year age difference between them. The duo were together for three years before getting married in August 2018 and having a child. It’s a little healthy and happy girl.
John Stamos — Caitlin McHugh (22 Year Difference)
John Stamos has long been regarded as a handsome idol, even after settling down. He and his current spouse met when filming a TV show in 2015. They quickly began a relationship which eventually led to marriage.
The 22 year age difference led many tabloids and pundits to speculate that the relationship wouldn’t last, but the two are still happily together and have a kid together named Billy.
Richard Gere — Alejandra Silva (34 Year Difference)
Richard Gere is an actor that you just can’t help but love, and more than a few people’s first celebrities crushes we’ll bet. In 2015 however he broke hearts after getting together with Alejandra Silva. The pair dated for some time before declaring their relationship publicly.
No one is sure whether the secret was because she is 34 years younger than him, or because they just didn’t want the attention. They got married in 2018 and have since had two kids.
Gavin Rossdale — Sophia Thomalla (24 Year Difference)
After a widely publicized and stormy breakup with popstar Gwen Stefani, Gavin Rossdale hit the ground running to get back into the dating world. In 2017 he began dating Sophia Thomalla, a German model.
The two seemed happy enough, but unfortunately, the relationship only lasted a single year. The media just couldn’t stop talking about the 24 year age difference, and the fact that Thomalla was younger than Rossdale’s oldest daughter.
Matthew McConaughey — Camila Alves (14 Year Difference)
Alright, alright, alright, what list of ladies men would be complete without Matthew McConaughey? He was a budding bachelor and heart breaker for many years. However he settled down in 2007 when he met Camila Alves, and the two wed in 2012.
Even though there’s a 14 year age gap between them, the duo seems very happy. In fact they’ve already had three kids over the past decade. Who would have thought he could be tamed?
Tony Benett — Susan Crow (40 Year Difference)
Even though his heyday is done, Tony Benett still seems to cause a stir by getting married for a third time in his long life. Bennet wed one Susan Crow in 2007.
It’s said that the two dated for about 20 years before eventually getting married. They met when Crow was in her 20s, but what’s interesting is that Crow’s Crows mother attended one of Benett’s concerts when she was pregnant with Susan! The 40 year age difference was irrelevant to them.
Jason Statham — Rosie Huntington-Whiteley (20 Year Difference)
Hardcore action star Jason Statham is married to someone 20 years his junior. The two have been together after meeting while filming Transformers: The Dark Moon.
They only went public a year after. It was still a whole year more before they were prepared to make it official and get married. The age difference appears to be no issue at all as the two are still happily together, often photographed smiling on the red carpet.
Jay-Z — Beyoncé (11 Year Difference)
Undoubtedly the strongest power couple in the music industry, Jay-Z and Beyoncé met in 2000, but only started dating a year later in 2001. They were wed in secret in 2008.
While still together, the two have had an at times rocky relationship, with rumors of cheating and other incidents. That said, they’ve managed to stay together and have three children. The 11 year age difference appears to be the least of their worries.
Jimmy Page — Scarlett Sabet (46 Year Difference)
Definitely one of the biggest gaps on this list, Led Zeppelin lead guitarist Jimmy Page is a whole 46 years older than Scarlett Sabet, his current girlfriend. They met in 2014 at a poetry reading in a bookshop.
Sabet’s words made a real impact on Page, and from there the rest is history. The age difference wasn’t enough to keep them apart, and the two have been happily together ever since.
Marques Houston — Miya Dickey (20 Year Difference)
Houston of Sister, Sister fame is a whole 20 years senior to his wife Miya Dickey. Dickey was just 19 when she and Houston tied the knot. Because of her age, scaladnous rumors have spread about the ignition of their relationship.
Some say Houston began his relationship with Dickey before she was legal, but he has disputed these claims. Even though the two are going strong year on year, the age gap is not an obstacle for them.
Julius Tenon — Viola Davis (12 Year Difference)
Julius Tenon began his career in college football, but eventually broke into the film industry. That is where he met his wife-to-be Viola Davis. He accidentally overheard her say she was looking for someone special, and he became that person.
They got married in 2003 and adopted a daughter together named Genesis. She was welcomed to the family in 2011. The 12 year age difference has had no negative effect on their relationship.
Patrick Stewart — Sunny Ozell (38 Year Difference)
Captain Picard or should we say Partick Stewart’s wife is a whole 38 years his junior. Stewart, of X-Men and Star Trek fame met Sunny Ozell through a friend in 2008. Five years later in 2013 they were wed.
According to Ozell, the only difficulty was meeting Stewart’s kids who are similar to her in age. Despite the huge age gap, the two get along very well and are happy. A few videos of them playing around have even gone viral.
David Cross — Amber Tambly (19 Year Difference)
Even though there’s a big difference in their ages, the pair has been wed for over a decade now. The duo had a chance meeting on a flight between Louisiana and Houston in 2007. Tambly, a fan of Cross’ work noticed the actor sitting a few rows over from herself.
A couple years later in 2001 they announced their engagement and got married in 2021. Despite the sizable difference in age, the two are going strong and happily married.
Warren Beatty — Annette Bening (22 Year Difference)
Warren Beatty, a well known Playboy, toned it down after he got together with Bening. Beatty was 54 years old and Bening was 33 years old when he approved her for a role in his 1991 film Bugsy.
Warren Beatty and Annette Bening (22 Year Difference)
Even though he said he wouldn’t ask her out until after the production, the flirting was too much and he asked her out to dinner. It wasn’t long before they realized they were a good match and got married a year later.
Bob Saget — Kelly Rizzo (23 Year Difference)
Full House star Bob Saget entered a marriage with Kelly Rizzo, with a 23 year age difference between the two. Rizzo is a well known foodie and traveler that hosts the Eat Travel Rock streaming series.
The two were acquainted in 2015 through a mutual friend. Saget then slid into her DMs on Instagram, and it skyrocketed from there. Three years after they were wed and it seems like the 23 year age difference isn’t an obstacle.
George Clooney — Amal Alamuddin (17 Year Difference)
George Clooney was famous for saying he’d never be wed, and that he’d stay a Hollywood playboy, but in 2013 his attitude changed when he met attorney Amal Alamuddin. Seems he tempted fate!
The pair started dating and then 12 months later they got married in Venice, Italy. It seemed that the 17 year age difference between them had no negative effects on their marriage at all. The two have been happily married since.
Michael Fassbender — Alicia Vikander (11 Year Difference)
Sometimes life imitates art. This happened when Alicia Vikander and Michael Fassbender played a married couple in the film The Light Between Two Oceans.
The 11 year age difference is certainly one of the smaller ones on this list and it had no impact on their relationship. The two were wed in Spain, and have been happily together ever since. It seems only the media cared about the age gap after all!
Randy Jackson — Simone (35 Year Difference)
Famed producer and later judge on the US singing show American Idol, Randy Jackson really opened his love life up to scrutiny when he gathered fame.
And there was a lot for the media to scrutinize about the fan favorite’s love life. Particularly the 35 year age difference between him and partner Simone. Not that they mind the attention. The two are still gladly together and going strong.
Jeffrey Morgan — Hilarie Burton (16 Year Difference)
Known for playing charismatic anti-hero Negan in The Walking Dead, and Mr Winchester, father to Sam and Dean in Supernatural, Jefferey Dean Morgan has done it all. When it comes to love however, his partnership with actress Hilarie Burton caused a lot of buzz.
The two started their courtship in 2009, and ten years later they were wed. The weighty 16 year age difference between the two wasn’t an issue, and they even started a family.
Michael Douglas — Catherine Zeta-Jones (25 Year Difference)
Definitely an A-list pairing, Michael Douglas and Catherine Zeta-Jone have been together for over 20 years now. When they first started their relationship, there was a lot of discussion of the 25 year age difference and the effects it might have had.
The buzz was much ado about nothing, because the two have been happily involved for a long time, even though they have had their challenges, but don’t all couples?