Like Leonardo DiCaprio, many of his Hollywood friends—including Orlando Bloom, Tobey Maguire, and Brad Pitt—have also been romantically involved with partners decades younger than themselves.

DiCaprio is currently smitten with his girlfriend, Italian supermodel Vittoria Ceretti, who is 24 years his junior. The 27-year-old runway star and the 51-year-old Hollywood actor have been dating since 2023. Standing 1.77 meters tall, Ceretti is among the world’s leading supermodels and was previously married to DJ Matteo Milleri from 2020 to 2023.

Bloom, a close friend of DiCaprio, recently drew attention after being spotted with much younger model Luisa Laemmel, who is 21 years younger than him. The 49-year-old actor and the 28-year-old model were seen leaving together after attending the Super Bowl at Levi’s Stadium in California on February 8. Witnesses said the pair sat side by side in the VIP section, chatting intimately throughout the game. The Pirates of the Caribbean star is believed to be dating again more than six months after his split from singer Katy Perry.

Maguire, 50—one of DiCaprio’s closest friends—was also spotted attending the 2026 Super Bowl with a much younger companion, 20-year-old model Mishka Silva. The Spider-Man star watched the game with Silva from a private suite. Photos later circulated on social media, sparking buzz due to the fact that his rumored girlfriend is only a year older than his daughter.

Previously, Maguire dated model Tatiana Dieteman, who is 17 years younger, from 2018 to 2021. He was formerly married to jewelry designer Jennifer Meyer, with whom he shares a 19-year-old daughter, Ruby, and a 16-year-old son, Otis.

Pitt, a longtime friend of the Titanic star, is currently in a passionate relationship with jewelry designer Ines de Ramon. She is 29 years younger than Pitt and, like him, is divorced with no children. The couple have been dating since 2022 and are reportedly living together at Pitt’s new mansion in Los Angeles. The 62-year-old actor was previously married to actresses Jennifer Aniston and Angelina Jolie.

Another famous friend of DiCaprio, actor Bradley Cooper, is also dating someone significantly younger—supermodel Gigi Hadid. Cooper, 51, and Hadid, 30, have been together since 2023 and are reportedly planning to get married. Sources say that despite their 20-plus-year age gap, the two share a deep connection, including the fact that both are single parents to young daughters. Cooper previously dated supermodel Irina Shayk, with whom he shares an 8-year-old daughter, Lea, while Hadid is the mother of 6-year-old Khai from her past relationship with singer Zayn Malik.