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?
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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 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. We can’t help but question these dating patterns, and we found a lot of men in Hollywood that date women half their age. 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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James Marsden
Image Credit: Gilbert Flores/WWD via Getty Images 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.
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P. Diddy
Image Credit: Brenton Ho/Billboard/Penske Media via Getty Images 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 had a 14 year age difference
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David Schwimmer
Image Credit: Photo by David Buchan/Variety/Penske Media via Getty Images. 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.
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Dennis Quaid
Image Credit: Rob Latour/Variety/Penske Media via Getty Images 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.
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Nicolas Cage
Image Credit: Photo by Michael Buckner/Variety via Getty Images. 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.
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Scott Disick
Image Credit: Chelsea Lauren/WWD/Penske Media via Getty Images 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.
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Leonardo DiCaprio
Image Credit: Kurt Krieger/Corbis via Getty Images 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.
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Jim Carrey
Image Credit: Gilbert Flores/Variety/Penske Media via Getty Images 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.
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Tyga
Image Credit: Swan Gallet/WWD via Getty Images 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.
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Hugh Hefner
Image Credit: Sara Cozolino/Everett Collection 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.
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Wilmer Valderrama
Image Credit: Nina Westervelt/Variety via Getty Images 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.
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Joaquin Phoenix
Image Credit: Michael Buckner/Variety via Getty Images 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.
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Al Pacino
Image Credit: Michael Buckner/Variety/Penske Media via Getty Images 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.
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William Shatner
Image Credit: Chris Carrasquillo/Variety via Getty Images 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.
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Sean Penn
Image Credit: Michael Buckner/Variety via Getty Images 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.
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John Mayer
Image Credit: Gilbert Flores/Variety via Getty Images At 32, John Mayer was romantically linked to 19-year-old Taylor Swift. Over a decade later, Mayer was seen on an alleged date with 22-year-old Kiernan Shipka.
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Jeff Goldblum
Image Credit: Nina Westervelt/Variety via Getty Images 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.
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Sir. Paul McCartney
Image Credit: Robert Altman/WWD/Penske Media via Getty Images 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.
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Kelsey Grammer
Image Credit: Paul Zimmerman/Variety/Penske Media via Getty Images 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.
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Sylvester Stallone
Image Credit: Kristina Bumphrey/Variety via Getty Images 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.
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Bruce Willis
Image Credit: Michael Buckner/Variety/Penske Media via Getty Images 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.
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Michael Douglas
Image Credit: Steve Eichner/WWD/Penske Media via Getty Images 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.
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David Foster
Image Credit: Ron Wolfson/Courtesy Everett Collection 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, Yolando Hadid, who was 15 years younger.
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Harrison Ford
Image Credit: Gilbert Flores/Variety via Getty Images 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.
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Donald Trump
Image Credit: Aurora Rose/WWD/Penske Media via Getty Images 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.
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Jerry Seinfeld
Image Credit: Paul Zimmerman/Variety/Penske Media via Getty Images 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.
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George Clooney
Image Credit: Gilbert Flores/Variety via Getty Images 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.
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Jason Statham
Image Credit: Chelsea Lauren/WWD/Penske Media via Getty Images 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.
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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.
