40 Celebrity Men Who Date Younger Women

Truth be told, we can’t get enough of celebrity relationships. We love to see who’s dating who, who just got engaged, and everything in between. We love seeing couples in love. But something we frequently scratch our heads at is when some of the most popular celebrities date people half their age over and over again — seriously, what do you talk about?

We know the “older men are sexier” is a cliched mindset as old as time, but sometimes celebrity men take on that mindset way too much and roll with it. All jokes aside, there are many wonderful, healthy relationships that have larger age differences — and that’s fine!

But we can’t help but be a bit confused when celebrities like Tobey Maguire, Leonardo DiCaprio, Wilmer Valderrama, and Steven Tyler continually date women nearly half their age.

Sometimes it ends with a happily ever after — like George Clooney and Michael Douglas. Or it gets, er, inappropriate — ahem, Hugh Hefner.

Check out which A-list male celebrities continuously date women anywhere from 10 years younger to more than half their age.

A version of this article was originally published in Nov. 2021. 

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Tobey Maguire

After his divorce from Jennifer Meyer, Tobey Maguire has only been linked to people a lot younger than him, like his ex-girlfriend, model Tatiana Dieteman, who was 17 years his junior. He has also been linked to model and influencer Mishka Silva, who is 30 years his junior, and in 2024, he was linked to model Lily Chee, who is over 20 years his junior.

Leonardo DiCaprio

If there’s one thing people know, it’s that birthday boy Leonardo DiCaprio apparently doesn’t date women after they turn 25.

It’s been a big topic of conversation, especially since he’s been in a relationship with 27-year-old model Vittoria Ceretti throughout the 2020s.

He previously dated model Camila Morrone, who is 23 years younger than him. He’s also dated quite a few younger women in the past, including model Nina Agdal, who was 17 years younger.

Rod Stewart

Rod Stewart almost exclusively dated women nearly or over 20 years younger than him. The most notable are model Rachel Hunter, who is over 20 years younger, and baby mama Kelly Emberg, who is 14 years younger than Stewart.

Jason Statham

Jason Statham and Rosie Huntington-Whiteley have been happily together for over a decade, but many still criticize the relationship for its nearly 20 year age difference. Before this relationship, we sense a bit of a pattern. He also dated actress Sophie Monk, 13 years younger, and actress Kelly Brook, 12 years younger.

George Clooney

Famous heartthrob George Clooney was known as a playboy who could never settle down. That is until he tied the knot with Amal Alamuddin, who is 17 years younger than him. Before Alamuddin, he dated Stacy Keibler for a couple of years, who is almost 20 years younger, and Elisabetta Canalis, who is 18 years younger than Clooney.

Jerry Seinfeld

Jessica Seinfeld and Jerry Seinfeld have been married for 21 years and have an 18 year age difference. Before that, he was linked to writer Jennifer Crittenden, who is 15 years younger, and Shoshanna Lonstein, who is over 20 years younger.

Donald Trump

So we won’t touch on his affairs or past controversy. Let’s talk about Donald Trump’s marriages and long-term relationships where the age difference was a bit bigger than expected. His current wife and former First Lady, Melania Trump, is nearly 24 years younger than him. Donald also was married to Marla Maples, who is 17 years younger than him.

Harrison Ford

Harrison Ford is another Hollywood titan who has a thing for younger women. Harrison Ford and fellow actress Calista Flockhart have been married for 11 years and have a 22 year age difference. Before Flockhart, Ford dated Minnie Driver, who is 28 years younger, and was linked to Star Wars co-star Carrie Fisher, who is 24 years younger.

David Foster

Before marrying Katharine McPhee, who is over 30 years younger than him, David Foster dated a few more women quite younger than him. Foster was linked to Selma Blair, who was over 20 years younger, Yolanda Hadid, who was 15 years younger.

Michael Douglas

Michael Douglas’s marriage to Catherine Zeta-Jones got a bit of backlash because of their 25 year age difference, but they seem to still be on cloud nine over 20 years later. Before Zeta-Jones, he was linked to Love Actually starlet Martine McCutcheon, who is over 20 years younger, and news reporter Elizabeth Vargas, who is 18 years younger.

Bruce Willis

Bruce Willis has been married to model Emma Heming Willis for nearly 15 years, and they have a 23 year age difference. He’s also been linked to adult model Karen McDougal, who is 16 years younger and was engaged to fellow actress Brooke Burns, who is over 20 years younger.

Sylvester Stallone

Sylvester Stallone has been happily married to Jennifer Flavin for over 30 years, but did you know that they have a nearly 30 year age difference? He’s also been linked to Peggy Trentini, who was 14 years younger, and Angie Everhart, who was over 20 years younger.

Kelsey Grammer

Frasier star Kelsey Grammer tied the knot with writer Kayte Grammer back in 2011, not caring about their 16 year age difference. But Kelsey has married women a lot younger than him before. Kelsey used to be married to Camille Donatucci Grammer, who was 13 years younger.

Sir. Paul McCartney

Sir Paul McCartney has been married quite a few times in his life to many talented women. But we noticed a bit of a pattern with his dating life. For instance, his current wife Nancy Shevell is nearly 20 years younger, one ex-wife Heather Mills is 25 years younger, and was even linked to Renée Zellweger, who is nearly 30 years younger than him. And that’s just the tip of the iceberg.

Jeff Goldblum

Despite his first two marriages being close in age, Jeff Goldblum has frequently dated women younger than him. For the past nine years, Goldblum has been dating Emilie Livingston, who’s 30 years younger than him. Before Livingston, he dated models Tania Raymonde and Lydia Hearst, both over 30 years younger than him as well.

John Mayer

At 32, John Mayer was romantically linked to 19-year-old Taylor Swift. Over a decade later, Mayer was seen on alleged dates with actress Kiernan Shipka, who is 22 years his junior.

William Shatner

William Shatner was married to Elizabeth Shatner for nearly 20 years, who was 27 years younger than William. And before his nuptials, he was in a long-term relationship with actress Nerine Kidd, who was nearly 30 years younger than Shatner.

Al Pacino

Al Pacino’s last two serious relationships had significant age differences. From 2009 to 2018, Pacino was dating actress Lucila Sola, who was over 30 years younger than him. Then from 2018 to 2020, he dated actress Meital Dohan and he was nearly 40 years her senior.

Joaquin Phoenix

Back in 2013, Joaquin Phoenix dated Allie Teilz, who is nearly 20 years his junior. And back in 2001, he had a fling with Anna Paquin, who was newly 18. Now, he’s engaged to fellow actress Rooney Mara. Despite having a ten-year difference, they seem as happy as can be with each other and their child.

Wilmer Valderrama

Either you know this all too well or this is news to you, but Wilmer Valderrama dates girls way younger than him. For instance, he dated Demi Lovato, Mandy Moore, and Lindsay Lohan when they were under 18 and he was well into his 20s.

Hugh Hefner

Hugh Hefner exclusively dated women far too young for him, some as young as 18 when he was in his eighties.

One such partner was his wife before he died, Crystal Hefner, who was 60 years younger than him when they got together, and adult model Anna Sophia Berglund, who was nearly 60 years younger as well.

Several of Hefner’s exes and staff have spoken out against him in the years since his death.

Tyga

Now Tyga is quite young himself, but he seems to have a thing for those even younger. He’s typically dated models younger than 25 like Demi Rose and reportedly Val Mercado. His most well-known relationship was with Kylie Jenner, who started dating her at age — er — 16 when he was 24.

Jim Carrey

Carrey dated fellow actress Ginger Gonzaga after meeting on the set of Kidding. They had a 22 year age difference. Before that, he dated make-up artist Cathriona White for three years, who was over 25 years younger than him.

Johnny Depp

Johnny Depp has dated many starlets from Winona Ryder to Vanessa Paradis. But his latest, tumultuous marriage to Amber Heard had a significant age difference of 23 years. His last substantial age difference was when he dated supermodel Kate Moss and he was 10 years her senior.

Steven Tyler

Steven Tyler has dated quite a few women over the years. Within recent years, he was engaged to TV personality Erin Brady, who was 22 years younger than him. Now, he’s been dating Aimee Preston, who’s nearly 40 years younger than him. But they have seemed happy together the past seven years.

Eddie Murphy

Eddie Murphy, the father of 11, has a pretty controversial dating history. His fiancée, model Paige Butcher, is nearly 20 years younger than him, but neither of them seems to mind. He’s also dated TV personality Rocsi Diaz, who was over 20 years younger than him, and Amber Rose, who was 23 years younger than him.

Dane Cook

Dane Cook has routinely dated women much younger than him, and his wife since 2023, Kelsi Taylor, is no different, with an age gap of 27 years. Before Taylor, Cook was reportedly in a three-year relationship with former Playboy Playmate Amanda Cerny, who was 21 years his junior.

Zach Braff

Former Scrubs actor Zach Braff made headlines in 2019 when he and actress Florence Pugh announced they were dating. The couple then received an outpouring of hate given their 21-year age difference. In August 2022, Pugh announced their split and explained why they kept it private in an interview with Harper’s Bazaar.

“We’ve been trying to do this separation without the world knowing because it’s been a relationship that everybody has an opinion on,” Pugh told the magazine. “We just felt something like this would really do us the benefit of not having millions of people telling us how happy they are that we’re not together.”

Adrien Brody

Adrien Brody hasn’t exclusively dated women much younger than him, but there have been quite a few. His ex Lara Lieto was 20 years his junior, as well as Keira Knightley, who’s 12 years his junior.

Sean Penn

Sean Penn’s last three relationships had large age differences. Most recently, he was married to actress Leila George, who was 32 years younger than him. Before that, he dated Minka Kelly, who was 20 years younger, and Charlize Theron, who was 15 years younger.

Now, he’s seemingly dating Valeria Nicov, a model in her 20s, when he’s in his mid-60s.

Scott Disick

After splitting from Kourtney Kardashian in 2015, Scott Disick was linked to a string of much younger stars including Bella Thorne, who is 14 years younger than him, Sofia Richie, 15 years his junior, and Amelia Hamlin, 18 years his junior.

Channing Tatum

After his divorce from Jenna Dewan, Channing Tatum went on to date Jessie J, who’s eight years his junior, Zoe Kravitz, who’s nine years his junior, and Inka Williams, who’s 19 years his junior.

Gerard Butler

Gerard Butler made news in 2025 for allegedly dating 29-year-old model Penny Lane, per The Sun. Reminder: this is a 25-year age difference, and not the first time he’s dated someone much younger than him.

From 2014 to 2020, he dated Morgan Brown, who was 17 years his junior. Along with that, he dated Mãdãlina Ghenea (18 years his junior), Martina Rajic (20 years his junior), Goga Ashkenazi (11 years his junior), allegedly Lindsay Lohan (16 years his junior), and Rosario Dawson (10 years his junior).

Jake Gyllenhaal

Jake Gyllenhaal infamously dated a 20-year-old Taylor Swift for a couple of months when he was 29, which is a romance and age gap fans have continued dissect in the years since.

Since 2018, he has been dating Jeanne Cadieu, who is 16 years younger than him.

Nicolas Cage

Nicolas Cage’s last two major relationships have had serious age gaps. Before his wife Riko Shibata, who’s nearly 30 years younger than him, he married Alice Kim Cage, who was 19 years younger than him.

Dennis Quaid

After separating from Meg Ryan, Dennis Quaid married a woman 17 years his junior and, after their split, wed Laura Savoie, who is 39 years younger than him, in 2020.

David Schwimmer

While David Schwimmer has normally dated people younger than him, his two relationships that have raised the most eyebrows was with Zoe Buckman, who’s 19 years his junior, and Tina Barrett, who’s 10 years his junior.

P. Diddy

Sean ‘Diddy’ Combs began dating singer Cassie when she was just 19 while he was 36. She has since accused him of physically and sexually abusing her throughout their 10 year relationship.

While he was on and off with Cassie, Combs dated model Gina Huynh, who was half of his age and also accused him of abuse. He also dated Amber Rose, who is 14 years his junior.

James Marsden

In late Oct 2023, James Marsden was seen smooching a 25-year-old model named Frederique Brons, which happened after his breakup from singer Edei, who was 25 years his junior. He also dated Rose Costa, who was 14 years younger than him and was linked to Suki Waterhouse, who is 18 years his junior.

Gavin Rossdale

After his marriage to Gwen Stefani, Gavin Rossdale has only been linked to women around half his age.

In 2017, he was dating Sophia Thomalla, an actress who was 27 when they got together (and he was 51 years old). Along with that, Courtlyn Cannan, who was in her late twenties, and he in his late 50s when they got together.

Same thing with his current girlfriend, Albanian singer Xhoana Xheneti, who was 33 when she and Rossdale started dating (with him being 57).

Clint Eastwood

Clint Eastwood was 66 years old when he married 30-year-old Dina Ruiz in 1996. The couple later separated in 2014. Since then he has been linked to Christina Sandera, who is reportedly 30 years young than him.

He previously welcomed a baby with actress Frances Fisher, who is 21 years his junior, in 1993, among a string of other age-gap romances.

Alec Baldwin

Since 2012, Alec Baldwin has been married to Hilaria Baldwin, who is 26 years younger than him. But this wasn’t his first age-gap romance.

In the early 2000s, Baldwin was briefly linked to his Shortcut to Happiness co-star Jennifer Love Hewitt, who is 21 years his junior, and was linked to Kristin Davis, who is 16 years younger.

Ryan Seacrest

Ryan Seacrest was almost twice now-ex-girlfriend Aubrey Page’s age when they started dating in 2021. He and the model, who is 23 years younger than him, split in early 2024.

Prior to that, he was in a 7-year relationship with Shayna Taylor, who is 17 years younger than him. And he was linked to former Miss Teen USA Hilary Cruz, who is 14 years younger than him.

Don Johnson

Melanie Griffith was just 14 years old when she first started dating future husband, Don Johnson, who was 22 at the time.

The Miami Vice star would go on to have many more age-gap romances including a rumored relationship with Jennifer Connely, who is 21 years younger. He was also rumored to have dated Jodi Lyn O’Keefe, who was 18 when she began playing his daughter on Nash Bridges, while he was 47.

Since 1999, he has been married to Kelley Phleger, who is 21 years his junior.

Bradley Cooper

Since late 2023, Bradley Cooper has been happily coupled up with Gigi Hadid, who is 20 years younger than him.

He is nine years older than the mom of his daughter, Irina Shayk, who he dated for four years. Prior to dating Shayk, Cooper dated Suki Waterhouse during her early 20s. The exes are 17 years apart.

Fred Armisen

Yes, Fred Armisen is on this list too. There’s his ex-wife Elisabeth Moss, who was 16 years his junior, along with exes Abby Elliott, who’s 20 years his junior, and Natasha Lyonne, who is 12 years his junior. He’s now married to Riki Lindhome, who is 13 years his junior.

Josh Hartnett

Josh Hartnett’s wife Tasmin Egerton is 11 years his junior, plus he dated Sophie Lie, who’s 10 years his junior, and Gemma Ward, who’s nine years his junior.