Hollywood celebs who are dating women decades younger than them(Photo Credit –Facebook/Twitter)
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Be it same-sex relationships or older actors dating younger women in showbiz, there have been some of the most fascinating love stories in the annals of the film industry. Recently, one such pair that caught the attention was the Spider-Man actor Tobey Maguire, who was spotted with Lily Chee, a model almost three decades younger than him.
However, he isn’t the only one in such a relationship. Here’s a list of all such romances in Hollywood, where the man is decades older than the woman in the relationship.
Bradley Cooper and Gigi Hadid
Popular Hollywood actor Bradley Cooper, 49, has been dating the 29-year-old American supermodel Gigi Hadid since 2023. The duo was first spotted together in October last year as they ventured out for a dinner date at Via Carota, New York City’s West Village neighborhood. While their relationship started as a casual fling, they have been going strong ever since, even packing on PDAs occasionally. Bradley and Gigi were captured kissing earlier this year when they went out for dinner with friends. Meanwhile, Bradley co-parents his daughter Lea with his former partner Irina Shayk. Gigi, on the other hand, shares the responsibilities of her daughter Khai with her ex and former One Direction singer Zayn Malik.
After his ugly divorce from Angelina Jolie, The Fight Club actor Brad Pitt is going strong with jewelry designer Ines de Ramon. The two, who have an age gap of almost three decades, were first seen together enjoying a concert in 2022. Prior to Pitt, Ines dated The Vampire Diaries’ lead, Paul Wesley. According to a report by PEOPLE, the 60-year-old actor was introduced to the 31-year-old jewelry designer by a mutual friend. Meanwhile, there are reports that state that Ines has moved in with Pitt, and the latter is even planning to ask her hand in marriage after courting her for over a year now.
Leonardo DiCaprio and Vittoria Ceretti
Leonardo DiCaprio is notoriously known for dating women under 25. At present, the Titanic star, who is now 49, has been dating the Italian supermodel Vittoria Ceretti, who just turned 26 in June. The two were first captured together during their rendezvous in Santa Barbara in August 2023. Leonardo and Vittoria reportedly met during the Cannes Film Festival at the premiere of Killers of the Flower in May 2023. The couple has been spotted together on various occasions, with reports even suggesting that the acclaimed Hollywood actor might settle down with the Italian beauty in the near future.
Al Pacino and Noor Alfallah
84-year-old Academy Award winner actor Al Pacino was first linked with 30-year-old Noor Alfallah in April 2022 as they were spotted together in Los Angeles. After a year, the couple welcomed their first child, a son named Roman Pacino, in June, which was Pacino’s fourth. Just a few days after the arrival of their baby, Noor filed for sole custody of her son, which led to rumors of their split. However, the couple rubbished such reports. In March 2024, Noor talked about her relationship with Pacino to Vogue Arabia and revealed that they connected over their mutual love for films.
Robert De Niro and Tiffany Chen
After parting ways with his wife, Grace Hightower, in 2018, 80-year-old Robert De Niro found love once again in the arms of 65-year-old martial arts instructor Tiffany Chen. While the pair first met on the sets of De Niro’s 2015 film The Intern, they were first spotted packing on PDA in 2021. The couple has kept their relationship under wraps and has refrained from speaking anything about it. In May 2023, the actor announced the birth of his seventh child, without specifically mentioning with whom. However, later, one of his co-stars confirmed that he and his girlfriend Tiffany welcomed their first child.
Tobey Maguire and Lily Chee
Not just Leonardo DiCaprio, but Tobey Maguire, popular for his role as Spider-Man, is known for dating women half his age. The 49-year-old recently made it to the headlines with news of his alleged relationship with 20-year-old model Lily Chee. The two were spotted at Michael Rubin’s White Party, celebrating the 4th of July. Their viral picture from New York’s star-studded event has taken the internet by storm. Unlike other couples on the list, there has been no confirmation about their affair yet.
Gerard Butler and Penny Lane
The 54-year-old Scottish actor Gerard Butler has reportedly found love again with Sports Illustrated model, Penny Lane, who is 25 years younger than him. The actor was spotted cozying up to the model as they enjoyed a stroll on the streets of Primrose Hill. They were later spotted at a local pub, where they were seen laughing together. Prior to the 29-year-old model, Gerard was in a nine-year-long relationship with Morgan Brown.
