Quite a few public figures have notably dated younger people. While some famous women, like Kris Jenner, are currently linked to men decades younger than them, several male celebrities have made headlines for their dating habits, especially football coach Bill Belichick.
Bill is dating his girlfriend, Jordon Hudson, who is 49 years his junior. Despite the criticism they’ve received over their age gap, the couple haven’t let it affect their relationship.
Below, Hollywood Life has compiled some of the most famous men who are dating younger women.
Kash Patel
Kash Patel started dating his girlfriend, Alexis Wilkins, in 2023, and they’ve been going strong ever since. The FBI director and the country music singer have kept their relationship away from the public eye, but Alexis was present during Kash’s swearing-in ceremony in early 2025. That February, Alexis shared a photo from the event on her Instagram, and she gushed about being “beyond proud” of her boyfriend.
According to Daily Mail, Kash and Alexis first met in October 2022 at a ReAwaken America event, and they started dating about two months later.
Kash and Alexis have nearly 20 years between them, with an age gap of 18 years.
Bill Belichick
As previously noted, Coach Belichick has been dating his girlfriend, Jordon, since 2023. They didn’t go public with their relationship until 2024.
According to TMZ, Jordon and Bill met in February 2021 while on a flight to Florida. The outlet published a selfie of the two of them mid-air, smiling for the camera. At the time, Jordon was attending Bridgewater State University. Bill and Jordon stayed in contact as friends before they eventually formed a romantic connection, per the outlet.
Bill and Jordon have an age gap of about 49 years.
Leonardo DiCaprio
It’s no secret that Leonardo DiCaprio tends to date women years younger than him. As of 2025, the movie star has been in a relationship with his girlfriend, Italian model Vittoria Ceretti. They were first linked in 2023, nd they have a 23-year age gap between them.
Before Vittoria, Leo briefly dated Gigi Hadid, who is 21 years younger than him, and he was in a relationship with ex-girlfriend Camila Morrone for five years. They had a 23-year age difference.
Michael Douglas
Michael Douglas has been married to his wife, Catherine Zeta-Jones, since 2000. The spouses started dating in 1999 and have a 25-year age gap. They share the same birthday: September 25.
Catherine and Michael celebrated their 25th wedding anniversary in November 2025, and the Terminal actress shared pictures from their ceremony on Instagram.
“25 years ago today, I walked down the aisle,” Catherine captioned her carousel post. “The intoxicating aroma of flowers, the glow of the candles, the resounding harmonious Welsh choir and you at the end of the long walk waiting for me, looking at me the way only you can. I love you today as I did then. Thank you, sweetheart.”
Sean Penn
Sean Penn has been dating his girlfriend, actress and model Valeria Nicov, since 2024. She is currently 30 years old, which makes Valeria 35 years younger than the One Battle After Another actor.
Bradley Cooper
Bradley Cooper, 51, has been dating supermodel Gigi Hadid, 30, since 2023. The couple first sparked romance rumors after being spotted on a dinner date in New York City and have remained together ever since. Despite their 20-year age difference, their relationship has continued to grow more serious, with Hadid describing their dynamic as “very romantic and happy” in a 2025 Vogue interview. The pair have made several public appearances together, including at major events throughout 2025 and 2026, and are still going strong.
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