Relationships with large age gaps are nothing new in Hollywood. However, there are some stars who have a noticeable tendency to date fellow stars who are significantly younger than they are. Leonardo DiCaprio recently made headlines after he broke up with his model girlfriend Camila Morrone soon after she turned twenty-five years old. Camila and Leo had been dating for several years, and Twitter users even predicted that he would break up with Camila because Leo has never publicly dated anyone above the age of twenty-five. The jokes on social media about Leo's most recent break-up have been ruthless to say the least.
Though the Wolf of Wall Street star's dating history is especially peculiar, he is not the only celebrity in Hollywood who tends to date people who are at least a decade younger. Sometimes, relationships with large age gaps can lead to controversy. Megan Fox and Machine Gun Kelly; now exes Zach Braff and Florence Pugh; and Aaron and Sam Taylor-Johnson have all faced criticism for the age gaps in their relationships. Continue reading to find out which celebrities have notoriously dated fellow stars who are way younger than they are over the course of their career.
8 Kate Beckinsale
Though Kate Beckinsale has mostly dated people close to her own age, in recent years, she has tended to date stars who are much younger. In 2017, she began dating former Wild 'N Out comedian Matt Rife. Then, after a brief fling with Jack Whitehall, Kate dated Pete Davidson for a few months in 2019. Most recently, Kate dated singer Goody Grace in 2020. Kate is over twenty years older than Matt, Pete, and Goody Grace.
7 Scott Disick
Reality star Scott Disick has been linked to many different women since his split from Kourtney Kardashian. Scott has reportedly dated actress Bella Thorne, influencer Bella Banos, model Megan Blake Irwin, model Sofia Richie, and Lisa Rinna's daughter Amelia Gray. All of these women are at least ten years younger than the thirty-nine-year-old father of three.
6 Wilmer Valderrama
Though Demi Lovato previously claimed that she and her ex Wilmer Valderrama did not officially start dating until after her eighteenth birthday, the lyrics in her new song "29" suggest that they may have been more than friends while she was still technically a minor. Wilmer also dated Lindsay Lohan when she was eighteen, and he was in his twenties. Wilmer's current fiancée allegedly over ten years younger than him.
5 Bruce Willis
Like many of the other celebrities on this list, Bruce Willis has been in the entertainment industry for several decades. He has been linked to many famous women, including Emily Sandberg, Nadia Bjorlin, Brooke Burns, and Lindsay Lohan. All of these women are at least a decade younger than the Die Hard actor. He is currently married to Emma Heming, who is over twenty years younger than him.
4 Diddy
Over the course of his long career, Diddy has been linked to many stars. Though Diddy has dated women closer to his age, like Jennifer Lopez, Kim Porter, and Cameron Diaz, he has also dated women who were born over a decade after he was. He dated Cassie on-and-off for about ten years. He also reportedly dated Miracle Watts, Lori Harvey, and Gina Huynh. He is now allegedly dating the City Girls' Yung Miami.
3 Sean Penn
After being in the entertainment industry for nearly fifty years, it is no surprise that Sean Penn has been in several high profile relationships. He has been married to Madonna, Robin Wright, and Leila George. Leila George is over thirty years younger than the Mystic River actor. Sean Penn has also been linked to Jewel, Scarlett Johansson, and Charlize Theron. They are all over a decade younger than Sean.
2 Sylvester Stallone
Sylvester Stallone has recently been making headlines after his wife announced their divorce after twenty-five years of marriage. Sylvester's soon-to-be ex-wife Jennifer Flavin was over two decades younger than him. Sylvester has also been linked to Angie Everhart, Peggy Trentini, and Janine Turner, who are all at least a decade younger than the legendary actor.
1 Dane Cook
Dane Cook recently announced his engagement to his now fiancée Kelsi Taylor. Kelsi is twenty-seven years younger than Dane, and some have questioned when exactly he started dating her. Dane allegedly dated Julianne Hough and Amanda Cerny when they were in their early 20s, and he was in his late 30s.
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