Some of the most interesting romances in Hollywood history have been those where the age difference was relatively large. Memes about Leonardo DiCaprio and his obsession with women 20 years younger continue to surface, but many people have also found love in such unconventional equations. In this article, we list some of Hollywood’s top male stars whose partners are decades younger.
1. Leonardo DiCaprio
The latest addition to DiCaprio’s life is 25-year-old model Vittoria Ceretti, who is 49 years old. She has been linked to him since August 2023, when they were spotted spending time together in Santa Barbara, California. They reportedly met at the Cannes Film Festival during the premiere of Killers of the Flower Moon in May 2023. Despite some rumors about their engagement due to the dazzling diamond ring worn by the Italian model on that finger, insiders have denied such claims, mentioning that they enjoy each other’s company and are getting to know each other deeply.
2. Brad Pitt
The 60-year-old Fight Club actor has been dating 31-year-old jewelry designer Ines de Ramon since late 2022. Following his divorce from Angelina Jolie, he was spotted with several other women, including Emily Ratajkowski. The couple was first spotted together enjoying a Bono concert in LA in November 2022 after the designer and her husband, The Vampire Diaries alumnus Paul Wesley, quietly split earlier that year. PEOPLE magazine reports that the two were introduced to each other by a mutual friend. At the LA premiere of Pitt’s film Babylon, the couple were seen mingling with other invitees, often hugging each other. Fast forward to 2024, Ramon is said to have moved in with the actor and they are quite happy together.
3. Bradley Cooper
Bradley Cooper, 49, has been romantically linked to supermodel Gigi Hadid, 29, since 2023. The actor, best known for his role in A Star Is Born, was first spotted dining together with Hadid at Via Carota in New York City’s West Village in October 2023. The couple was first spotted kissing at dinner with Hadid’s friends, Queer Eye’s Tan France and Antoni Porowski, in March 2024. Given their busy lives and the fact that both stars have children from previous partners, what started out as a casual fling has turned into a more serious relationship in recent times.
4. Al Pacino
The 84-year-old movie star went viral when his rep told US Weekly that he is expecting his first child (his fourth overall) with girlfriend Nour Alfallah (30) in May 2023. They were first spotted together at Felix Trattoria in Los Angeles in April 2022. They welcomed baby boy, Roman Pacino, in June 2023, but Alfallah soon filed a request for sole custody, with ‘reasonable visitation’ for Pacino. This sparked separation rumours, but they confirmed they are still together and have reached an agreement regarding custody of their son.
5. Robert De Niro
De Niro, 80, has been in a more or less private relationship with martial arts instructor Tiffany Chen, 65, since 2021. They were reportedly first linked on the set of The Intern in 2015, during which time the Taxi Driver actor was still married to Grace Hightower, whom he divorced in 2018. The couple were spotted together on a European vacation in 2021, but have kept pretty low key about their romance. In May 2023, they welcomed their first child, Gia (De Niro’s seventh). Despite the internet outrage, the actor claimed it was a planned pregnancy.
6. Tobey Maguire
Just like DiCaprio, the Spider-Man star is also notorious for dating girls much younger than him and the latest name on his list is 20-year-old model Lily Chee. The 49-year-old actor was spotted with Chee at Michael Rubin’s White Party, one of New York’s most famous social events. Their viral pictures from the party have taken the internet by storm, but neither of them has made any official confirmation about their relationship.
