Leonardo DiCaprio, GF Vittoria Ceretti cross paths with Robin Thicke during bike ride

Leonardo DiCaprio and girlfriend Vittoria Ceretti enjoyed a laid-back day in New York City this week, where the couple’s bike ride included an unexpected reunion with one of the actor’s longtime friends, Robin Thicke.

The Titanic star, 51, and the Italian model, 28, were photographed riding Citi Bikes through the city before stopping to chat with Thicke, who happened to cross paths with the couple on a sidewalk.

Keeping a low profile, DiCaprio, Ceretti and the “Lost Without U” singer all wore dark sunglasses as they caught up during the chance encounter.

DiCaprio and Thicke have shared a friendship for decades. According to Entertainment Tonight, the two first became close in the early 1990s when DiCaprio joined the cast of the sitcom Growing Pains, which starred Thicke’s late father, Alan Thicke.

The friendship has continued over the years, with DiCaprio attending Thicke’s wedding to April Love Geary in Cabo San Lucas, Mexico, in May 2025.

The New York outing also offered another glimpse into DiCaprio’s relationship with Ceretti, whom he has been dating since they were first linked in August 2023.

The pair initially sparked romance rumors after they were photographed together in Santa Barbara, California, enjoying a casual outing with iced coffees and ice cream.

Earlier this year, the couple made their awards show debut at the 98th Academy Awards. Although they skipped the red carpet together, they were seated side by side inside the ceremony, where DiCaprio was nominated for Best Actor for his performance in One Battle After Another.