40 Famous Men Whose Girlfriends Keep Getting Younger and Younger

Steven Tyler is one of the most iconic rock ‘n’ roll stars ever. Over his decades with Aerosmith, he has garnered many awards and a lot of attention, especially for those that he struts around with on his arm.

One of these just so happened to be his assistant, Amy Ann Preston. This young professional was romantically linked with the rockstar despite their 41-year age gap.

Leonardo DiCaprio has been in the entertainment industry since he was a young kid, and because of this, all eyes have been on him during his entire dating life. With his undeniable talent on screen, it’s no surprise that Leo has found his way into some pretty public relationships.

One of these relationships is with the beautiful Camilla Morrone, who has been seen around town with him. This couple has a 23-year gap, but it doesn’t seem to phase them one bit.

Al Pacino has been a pretty consistent feature in Hollywood for decades. Always the bachelor, he has been linked to several other famous actresses when it comes to romantic relationships.

Though many of these women were closer to his age, it seems that for right now, he’s settled on dating Israeli movie star Meital Dohan — who is 39 years his junior.

Over his illustrious and lengthy career, Sean Penn has been married several times to some pretty big names. Among those, of course, are Madonna and Robin Wright, but once those relationships were over, it seems Sean turned to the younger crowd.

In doing this, he found himself in a pretty public relationship with a much younger woman. Layla George, who was linked to him in 2019, is 32 years younger than the A-list actor.

Dennis Quaid, after having three failed marriages, still wanted to have a meaningful relationship. So the 65-year-old actor found a way to make his dating life more private and eventually ended up proposing to a much younger woman.

Just four months after meeting Laura Savoie, he popped the question despite their 39-year age gap. Since then, they have tied the knot and seem to be very happy together.

Both Tom Cruise and Katie Holmes have made their mark in Hollywood — on the big screen and the small screen. Before Katie, though, Tom had other relationships with the likes of Nicole Kidman and Mimi Rogers.

Eventually, though, Tom Cruise found himself falling for a young woman, 16 years younger, to be exact. Yet, it didn’t seem to bother either of them one bit. Although the couple did part ways, the age difference was not the culprit.

Pete Cook may not be a name that everyone recognizes, but this architect was launched into the limelight when he became Christie Brinkley’s husband. After they divorced, Pete began dating women a little bit younger than his ex.

In fact, he found himself falling for Alba Jancou, who’s just 21 years old. This means they have a 39-year age gap and that his significant other is younger than his daughter. That didn’t stop him from proposing to his beloved girlfriend, though!

Zach Braff seems to have a thing for younger women now but he didn’t always. He had been romantically linked to big stars including Kirsten Dunst and Drew Barrymore, but eventually, he found love in a much younger actress.

Zach Braff has been in a relationship with Florence Pugh since 2019 — despite their 21-year age gap. The Black Widow star and her beau have had to defend their relationship on numerous occasions but they seem to have an undeniable connection.

Michael Sheen has recently been making waves on the show Prodigal Son, but that isn’t the only place many people feel he rocks the boat a bit. After his marriage to Kate Beckinsale ended, Sheen found himself involved with a beautiful, young woman named Anna Lundberg.

The couple seems to be happy and making it work, though there is a 25-year age gap. They even welcomed a baby in September of 2019.

Following his very public divorce from Camille Grammer on the hit reality TV show Real Housewives of Beverly Hills, Kelsey wanted a more low-key relationship.

Eventually, the 64-year-old actor met Kayte Walsh, who is 25 years younger than him, and they quickly fell for each other. Before long, the pair was walking down the aisle and becoming man and wife.

It seems that many Hollywood stars, after having a traumatic breakup, turn to partners that are the complete opposite of the person they just left. That’s the case with the musician Robin Thicke, who had a pretty intense breakup with his previous wife, Paula Patton.

Still, it must not have been too tragic because months later, Thicke began to date a new woman, model April Love Geary. They seem to be pretty smitten with each other, especially considering the fact that they’ve welcomed three children together.

Dane Cook is a pretty popular comedian who likes to keep things on the edge. Maybe that’s why he opted to go for a younger woman, Kelsi Taylor, when he began dating. However, it seems to be working because they’ve been together for quite a while.

After initially meeting each other at a game night at Cook’s house, the two quickly developed a relationship, and even with a 26-year age gap, they still have a lot in common.

There are lots of great stories when it comes to romantic entanglements, and how a couple meets. David Foster and Katharine McPhee first met when Katharine was a contestant on the fifth season of American Idol. Because Katharine was going to be performing a song that was originally written by David, he stopped by to help her practice.

With David as her mentor, the two developed a friendship and eventually, in 2018, announced their engagement. Of course, the media focused on their 34-year age gap rather than the relationship itself.

Sean Combs has been in showbiz for decades, and because of this, he has been attached to several high-profile relationships with the likes of Jennifer Lopez. One of the longest, though, was with the singer Cassie.

When this relationship eventually fell apart, the entrepreneur began dating Lori Harvey. The two had a 28-year age gap, and that may be why the relationship only lasted three months.

The relationship is long over, but it seems that Wilmer Valderrama has a thing for younger women. In the past, his preferences gained a lot of attention, especially when it came to his six-year relationship with singer Demi Lovato.

With a 12-year age gap, the couple still seemed to be able to manage their differences. However, the two broke up eventually and moved on with their lives. Today, Wilmer is engaged to Amanda Pacheco — with whom he shares a child.

Hearing Sylvester Stallone’s name automatically conjures up images of a sweat-clad boxer punching a slab of meat. Perhaps his most iconic role, Rocky, also introduced him to his sweetheart — who he’s been with for over two decades!

Stallone met wife Jennifer Flavin on the set of Rocky V when he was 42, and she was 19. After 24 years together, they seem to have absolutely no issues with their 22-year age gap.

Though Mel Gibson has had some pretty controversial moments over the past couple of decades, he’s still one of the most iconic actors in Hollywood. Because of his place in the entertainment industry, any relationship he has gains a lot of attention.

That includes his relationship with Rosalind Ross, who is 35 years younger than him. This large age gap could be a problem for some, but it doesn’t seem to be for them.

Ben Affleck has recently been making headlines for rekindling his famous relationship with J.Lo. They seem to be happy, but in between the time of Affleck’s divorce from ex-wife Jennifer Garner and now, he has had several relationships with younger women.

One of those was with a Saturday Night Live producer, Lindsey Shookus. Though the age gap was minimal, just a measly eight years, it might have been a deal-breaker. The relationship didn’t last, but Ben did move onto other younger women.

Chris Pratt has become quite the leading man over the past several years, and this has made his romantic relationships that much more press-worthy. After he and his ex-wife, Anna Faris, split, Chris eventually found a new love.

Although they are 11 years apart, Pratt and Katherine Schwarzenegger eventually sealed the deal by walking down the aisle and exchanging vows. They have since welcomed a child together.

With several marriages under his belt, Billy Joel still didn’t lose hope and continued looking for “the one.” After both his marriages to Christie Brinkley and food writer Katie Lee ended, he found love again with his fourth wife.

Dating a woman half his age seems to be working out just fine. The musical genius exchanged vows with Alexis Roderick in 2015, and the two have been enjoying life ever since — despite their 32-year age gap.

We’re back to Ben Affleck! After his divorce from Jennifer Garner, the star had several consistent relationships with younger women — though all of them obviously ended considering that he and J.Lo have been making headlines for getting back together.

Still, some of Ben’s previous relationships are worth mentioning. He was romantically linked to Ana de Armas, a Cuban movie star who happens to be 16 years younger than the award-winning actor.

Scott Disick rose to fame as the boyfriend of Kourtney Kardashian on the hit reality television show, Keeping Up With the Kardashians. Eventually, though, Scott and Kourtney ended their on-and-off relationship — and Scott finally moved on.

In 2017, Disick decided to let the world know that he had been dating Lionel Richie’s daughter, Sofia Richie, who’s 15 years his junior. This is a unique relationship because Richie is also close friends with many of the members of the Kardashian family. As of 2020, however, they’re no longer together.

Alec Baldwin has been a fixture in the Hollywood scene for decades and has had several high-profile relationships, including his stormy marriage to actress Kim Basinger. When that relationship ended, many people were desperate to see who the next woman on his arm would be.

Alec eventually met Hilaria Thomas — and the two, despite their 26-year age gap, instantly clicked. So much so that they ended up tying the knot. They now have four children together.

It must be hard to maintain a marriage when the spotlight is always on you. Josh Duhamel was married to musician Fergie for eight years when they decided to split.

Since this breakup, Josh has been linked to several people but most recently to model Audra Mari. 21 years younger than Josh, Audra was crowned Miss World America 2016.

Harrison Ford has played many iconic roles and has been the subject of many tabloid stories regarding cheating. But perhaps, after finding love with Calista Flockhart, all of that is behind him.

Calista Flockhart, who is 22 years younger, and Harrison have been together since 2002 and share a child. It seems that the age gap may have worked its magic in this case.

Nicolas Cage had already been married twice before he finally met his third wife, Alice Kim. These two met at a sushi restaurant where Kim was a waitress, and they hit it off. Eventually, they got married.

Whether it was the 20-year age gap or simply because their relationship just wasn’t working, the two eventually split up. But, this wouldn’t be the last younger woman that Cage would attach himself to.

Jeff Goldblum tried his hand at marriage a couple of times throughout the ’80s and failed on both accounts. Though each marriage ended on its own accord and for different reasons, it seemed that Jeff was out of luck when it came to love.

That was until 2014 when Jeff Goldblum met Emilie Livingston. Emilie — who is 30 years younger than Jeff — has stood by him since, and they even have two children together.

Bruce Willis and Demi Moore made for one of the most iconic ’90s couples. Still, their marriage eventually ended, although the two remain friends to this day. In any event, Moore and Willis went their separate ways. Eventually, though a decade after the divorce was over, Bruce would find new love.

Although Willis had different relationships over the years, none of them stuck until he met Emma Hemming, who is 24 years younger than him. The two fell head over heels for each other — so much so that they got married in 2009 and have welcomed two children ever since.

Lorenzo Lamas may not be as big a star as some of the others, but he had his run on hit television shows like Falcon Crest. After four failed marriages, it seemed that Lorenzo was perpetually going to be the single bachelor — that is, until he met Kenna Nicole Smith.

After being introduced to each other through his godmother, Lorenzo and Kenna eventually began dating despite their 27-year age gap. Soon, their relationship blossomed into marriage, and now, the two are inseparable.

74-year-old actor James Woods has had plenty of time in the limelight when it comes to romantic relationships. With two previous marriages, it seemed as if he was done with that aspect of his life.

Until he met Sarah Miller, of course! Despite their 42-year age gap, Woods and Miller just can’t resist each other. The critically-acclaimed star recently sparked engagement rumors when he was spotted at a restaurant with his 32-year-old girlfriend — who was sporting a huge diamond on her ring finger.

After his marriage to Alice Kim ended, Nicolas Cage began dating again. This time, though, he thought he would try a younger woman to see if that could make things work. So, at the Independent Spirit Awards in 2020, he made his relationship with Riko Shibata public.

The two have a 30-year age gap. Still, that doesn’t seem to bother them much, as just a month after making their debut, the two tied the knot.

It looks like Sofia isn’t the only Richie to make the list! Lionel Richie has been singing romance songs for decades and, naturally, has had many romances himself. But, back in 2014, when Lionel began dating Lisa Parigi, he kept it extremely quiet.

It wasn’t until 2021 when the relationship was suddenly put on blast, and people began discussing the 40-year age gap. Even with all the backlash on social media, though, the two remain deeply in love.

Over the last several years, Brad Pitt has been in the public eye due to his divorce from Angelina Jolie. With so much being exploited by paparazzi and tabloid press, you might think that Brad would stay away from any type of romantic entanglement.

But, in 2020, he was seen out and about with a new woman named Nicole Poturalski. This German model seems to be Brad’s new love interest despite their 29-year age gap.

Dolph Lundgren got his start in the movie industry as a Russian boxer in one of the Rocky sequels. Since then, he has been in several movies and continues to work to this very day.

However, his romantic relationships have fallen under the radar until his newest one with a Norwegian personal trainer named Emma Krokdal. This relationship has found its way into the news thanks to the couple’s 38-year age gap.

Vincent Cassel is a French actor known for his roles on both television and in films including Westworld and Ocean’s 12. He’s not only popular for his movie roles, where he tends to play a tough guy, but he’s also known for his real-life romantic relationships.

He and his current wife have a 30-year age gap. The couple dated for three years before tying the knot in August 2018. Soon after, they welcomed a baby girl to the world!

John Stamos was — and still is — a heartthrob whether or not he has finally settled down. In any case, he and his wife met while filming an episode of a television show in 2015. They soon began dating and eventually got married.

With a 22-year age gap, many thought that this relationship was doomed to fail, but the two of them are still madly in love. They have one child together, named Billy.

Richard Gere is one of those actors that almost every woman has had a bit of a crush on at one point or another. But, in 2015, Alejandra Silva seemed to nab him up. The two dated for a while before making their relationship public.

Maybe this was because of the 34-year age gap, or perhaps it was just because they wanted to have a little private time to themselves. The two finally married in 2018 and have had two children since.

After a very public and messy divorce with his rockstar wife, Gwen Stefani, Gavin Rossdale didn’t waste any time to get back into the dating scene. In 2017, he began seeing German model Sophia Thomalla.

The relationship only lasted a year, however. Everybody couldn’t help but talk about the 24-year age gap and the fact that Gavin was dating a woman that was a year younger than his oldest daughter.

Matthew McConaughey may strike some as a perpetual ladies man, but in 2007, he met someone who would change that — Camila Alves. Clearly, something stuck because they tied the knot in 2012.

Despite the 14-year age difference, the two seem to be very much in love — so much so that they have even welcomed three children together!

Though Tony Benett’s glory days are way past him, it seems like he is still in the business of producing new sensations by getting married for the third time in his life. Bennett married Susan Crow in 2007.

Rumor has it that they have been dating for some 20 years before finally tying the knot. They first met when Crow was in her 20s, attending one of Benett’s concerts. What’s even more surprising is that Bennett met Crow even before she was born – as a fetus when her mother attended a concert of his. The 40-year age gap didn’t stop them, however, from ending up together.

The iconic anti-hero is married to a woman who is 20 years younger than him. Apparently, they have been married since 2010. The two met on the set of the film Transformers: The Dark Moon.

They only made it official a year later, however. Another year had to go by until both decided that they are ready to take their “official” status to the next level or settle down as we like calling it. The 20-year age gap is clearly not an issue in this relationship.

Dubbed as the most famous duo in the music world, Jay-Z and Beyonce can definitely be called the ultimate king and queen of the contemporary pop scene. They first met in early 2000 but didn’t start dating until 2001. They got married in 2008 in secret.

Since then, as rumors had it, there have been cheating incidents and other scandalous affairs that decorated the couple’s relationship. Yet despite their rough journey together, they managed to keep the package together and even have three kids. Needless to say that their 11-year age gap hardly puts a strain on their relationship.

Jimmy Page, the lead guitarist of Led Zeppelin and the twice-married rock legend, is 46 years older than his girlfriend Scarlett Sabet. The couple met in 2014 when Page stopped by a bookshop where Sabet was reading her poetry.

Apparently, Page was really moved by Sabet’s words and one thing led to another. The couple has been dating for six consecutive years since around that time at the bookshop. It appears that the 46-year gap between the two ain’t gonna stop’em!

Houston, who is better know

n as Mark Evans from Sister, Sister, is twenty years older than his (really) young wife. Dickey was only 19 years old when she married Houston. Given his wife’s tender age, ugly rumors have spread about the onset of their relationship.

Some claimed that Houston began dating Dickey before she was an adult. These rumors were denied by Houston. We wish them nothing but a long and happy married life and may their 20-year gap never do them apart.

Tenon, who actually started his career as a football player in college and ultimately ended up in the film industry, met his future wife Viola Davis by accident when he overheard her saying she wanted to meet someone “special.”

They have been married since 2003 and even adopted a daughter together, Genesis, in 2011. It seems like the 12-year gap between the two hasn’t really stopped them from having a wonderful relationship for so many years now.

Professor X’s, or rather Patrick Stewart’s wife is 38 years younger than him. Stewart, who is also known for playing Captain Jean-Luc Pickard in the Star Trek franchise, met Ozell, a Jazz singer, in 2008 through a mutual friend. The two dated for five years and finally decided to get married in 2013.

The only difficulty they had, reportedly, is Ozell meeting Stewart’s children who were relatively close to her in age. Other than that, it seems that despite the 38-year gap, these two love birds do get along just fine.

Despite the huge difference in age, the couple has been married for over ten years now. The two met on a flight from Houston to Louisiana in 2007. Tambly, who was a fan of Cross, got excited by noticing the actor sitting not too far from her.

Four years later, in 2011, they got engaged and ultimately married a year later. The way it seems, despite the 19-year age gap their relationship has been going strong nonetheless.

Warren Beatty, a notorious Hollywood bachelor, changed his ways for good when he met Bening. Bening was 33 years old and Beatley was 54 years old when he cast her for a role in his movie Bugsy in 1991.

Although he promised that he wouldn’t hit on her until the filming was over, he broke that promise towards the end and asked her out for dinner. It didn’t take long for the couple to realize that it was it as they got married a year later. Additionally, their 22-year gap had no effect on their relationship as they have been together ever since.

Bob Saget who is best known for his role in Full House, married Kelly Rizzo who is 23 years younger than him. Rizzo, in case you didn’t know, is a food and travel blogger who also hosts Eat Travel Rock streaming series.

Saget met Rizzo in 2015 through a mutual friend. Saget then sent her a direct message via Instagram and it all took off from there. Three years later they decided to get married and it seems like the 23-year gap between them doesn’t stop them from enjoying each other’s company.

Silverfox George Clooney had gone on record saying that he was never going to get married. He would perpetually be a Hollywood bachelor, but in 2013, his outlook on marriage changed when he met a beautiful, young attorney.

Amal Alamuddin and George began dating and a year later, they became husband and wife in Venice, Italy. It seemed that the 17-year age gap didn’t make any difference whatsoever to their relationship.

Sometimes in Hollywood, you can find love on the sets of films. That’s what happened between Michael Fassbender and Alicia Vikander, who played a married couple in the movie, The Light Between Two Oceans.

The 11-year age gap doesn’t seem to make any sort of difference as, one year later, the two got married in Spain. Clearly, their age difference is a bigger deal to the media than it is to them!

Randy Jackson was a well-known music producer before becoming a judge on the popular singing competition show, American Idol. Once he stepped into the limelight, though, he opened himself up for interest in the romance department.

This includes his relationship with musician Simone. The two have a 35-year age gap between them, but this doesn’t seem to stop them from enjoying each other’s company.

From starring in the hit horror show The Walking Dead to playing father to Dean and Sam in Supernatural, Jeffrey Morgan has been everywhere. But, when it comes to romantic endeavors, his relationship with fellow actor Hilarie Burton is the thing that got the most attention.

The couple began dating in 2009 and a decade later, walked down the aisle. It seems that the 16-year age gap has made no difference to them, even when it came to starting a family.

Perhaps one of Hollywood’s most dazzling couples, Michael Douglas and Catherine Zeta-Jones have been together for over two decades. When they initially started dating, there was a lot of talk about the 25-year age gap and its effect on their relationship.

Clearly, their age difference has nothing on them, as they’ve been happily married for quite a long time — despite having to face serious issues over the years.