Chelsea Handler, 49, made a revealing confession on The Tonight Show Starring Jimmy Fallon, expressing her infatuation with actor Robert De Niro, 80. Handler disclosed, "I feel sexually attracted to Robert De Niro, I always have and I would like to be penetrated by him." This admission was made on a night when De Niro was also a guest on the show, accompanied by his girlfriend, Tiffany Chen, 45. Handler admitted to feeling awkward about approaching De Niro backstage due to Chen’s presence, saying she didn't want Chen to think she was trying to make a move.
This revelation follows Handler’s recent comedic critique of older men fathering children late in life. She previously targeted De Niro, who at 79 had announced the birth of his daughter, Gia, with Chen. Handler humorously criticized De Niro along with Al Pacino, Alec Baldwin, and Elon Musk for their numerous offspring, joking about an "epidemic" of "horny old men who won't stop spreading their seed."
Handler’s dating history includes relationships with older men such as André Balazs, 67, and Ted Harbert, 68. Her last known relationship was with comedian Jo Koy, 52, which lasted nearly a year before ending in summer 2022. Despite the split, Handler has expressed warm feelings towards Koy. She also nostalgically recalled her brief romance with 50 Cent in 2011, describing him as "fun" and "a sweetheart."
Robert De Niro began his relationship with Tiffany Chen in 2021, following the end of his two-decade marriage to Grace Hightower.