Some of the most intriguing romances in Hollywood history have been the ones involving a relatively large age-gap. While memes about Leonardo DiCaprio and his fixation over 20-year-old women keep rolling out, many have found love even in such unconventional equations. In this piece, we have listed some of the top male Hollywood stars with partners who are decades younger.

1. Leonardo DiCaprio

The latest 25-year-old model in DiCaprio’s life, who is 49, is Vittoria Ceretti, with whom he has been linked since August 2023, when they were spotted enjoying 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 certain rumours about their engagement, owing to a sparkly diamond ring worn by the Italian model on that finger, insider sources have denied such claims, mentioning that they enjoy each other’s company and are getting to know each other on a deeper level.

2. Brad Pitt

The Fight Club actor, 60, has been dating jewellery designer Ines de Ramon, 31, since late 2022. After his divorce from Angelina Jolie, he was seen with several other women, including Emily Ratajkowski. The couple was first spotted together in November 2022, enjoying a Bono concert in LA, after the designer and her husband, The Vampire Diaries alum, Paul Wesley, quietly separated earlier that year. PEOPLE magazine reports that the two were introduced to one another by a mutual friend. At the LA premiere of Pitt’s film Babylon, the couple was seen mingling with other invitees, often with their arms around 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 involved with supermodel Gigi Hadid, 29, since 2023. The actor known for his role in A Star is Born, was first spotted with Hadid in October 2023, dining together at Via Carota in New York City’s West Village. The couple was first spotted kissing in March 2024, at dinner with Hadid’s friends, Queer Eye's Tan France and Antoni Porowski. What started as a casual fling, considering their busy lives and the fact that both the stars have children with previous partners, has evolved into a more serious relationship in recent times.

4. Al Pacino

The 84-year-old movie star went viral when his rep revealed to US Weekly that he was expecting his first child (his fourth overall) with girlfriend Noor Alfallah, 30, back in May 2023. They were first spotted together at Felix Trattoria, 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 led to rumours of a split, but they confirmed that they are still together and have reached an agreement regarding custody over their son.

5. Robert De Niro

De Niro, 80, has been in a more or less private relationship with 65-year-old martial arts instructor, Tiffany Chen, since 2021. They were reported to have first linked at the set of The Intern in 2015, during which period the Taxi Driver actor was still married to Grace Hightower, whom he divorced in 2018. The pair were spotted together on a European vacation, in 2021, but have been quite low-key about their romance. In May 2023, they welcomed their first child together, Gia (De Niro’s seventh). Despite internet outrage, the actor claimed that it was a planned pregnancy.

6. Tobey Maguire

Much like DiCaprio, the Spider-Man star is notorious for dating women much younger women and the newest addition to his list is 20-year-old model, Lily Chee. The actor, 49, was seen together with Chee at Michael Rubin’s White Party, celebrating Fourth of July, which is one of New York’s most star-studded social events. Their viral pictures from the party have taken the internet by storm but there is no official confirmation about their relationship from either of the two.

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