Resurfaced 1995 clip shows Uma Thurman dodging Letterman’s creepy questions about dating older men

"What's the oldest man you've ever gone out with?" David Letterman asked Uma Thurman in 1995.
PUBLISHED FEB 25, 2025
(L) Uma Thurman at the 53rd Cannes Film Festival, France 2000; (R) David Letterman at home, Westchester County, New York, March 1984.(Cover Image Source: Getty Images| (L) Hulton Archive; (R) Photo by Susan Wood)
(L) Uma Thurman at the 53rd Cannes Film Festival, France 2000; (R) David Letterman at home, Westchester County, New York, March 1984.(Cover Image Source: Getty Images| (L) Hulton Archive; (R) Photo by Susan Wood)

'Kill Bill' star Uma Thurman is known for portraying unconventional roles on screen, in 1995 she essayed the role of an American nanny who falls for an older man in the romantic comedy 'A Month by the Lake'. The subject being controversial it was bought up by television host David Letterman while Thurman appeared to promote her film on his late-night show. As per The Things, Letterman tried hard to pry into the 'Pulp Fiction' actress' dating life by asking her questions like, "Have you ever been married yourself?" "Would you, yourself, date an older man? What's the oldest man you've ever gone out with? You're 25, ever been out with a guy 30?" Thurman although uncomfortable ignored his queries and kept discussing her on-screen character. 



 

Letterman pointed out that he wasn't interested in her film, "Okay. I'm not talking about the film now. We'll talk more about you." But the Golden Globe winner did not budge from her stance and finally, the television host had to give up. But before moving on Letterman cheekily commented, "I know now that I'm going to stop asking you about this miserable part of your life. But god, your ears are just perfect." During the interview, Thurman remained tight-lipped about her past relationship with filmmaker Gary Oldman. As per InStyle, the couple met on the sets of 'State of Grace' in 1989 and got married in 1990. 

Uma Thurman and Gary Oldman circa 1990 in New York City. (Image Source: Getty Images| Photo by Robin Platzer)
Uma Thurman and Gary Oldman circa 1990 in New York City. (Image Source: Getty Images| Photo by Robin Platzer)

In the comments section of the YouTube video, one person wrote, "Yeah as a man, this is creepy. Young woman, old man, I don't think she was picking up what he was laying down. She seemed embarrassed." Defending Letterman's humour, another one wrote, "Give me a frigging break. This is a frigging comedy show. What line was crossed exactly?? Are we all turning into easily offended, hyper-triggered, perfectly behaved automatons?" Slamming Letterman, a few YouTube users commented, "Creepy," and "Cringe."



 

This wasn't the specific instance where Letterman appeared to be obsessed with Thurman; that year, he had tried to make a lame joke during the 67th Oscars, but it fell flat. During the opening monologue, the veteran host spotted Oprah Winfrey in the crowd and also Thurman. After that, he made a frantic effort to showcase how similar Winfrey and Thurman's first names were by repeating them. According to The Hollywood Reporter, in 2020 Letterman celebrated 25 years of the infamous “Oprah-Uma" moment. "And I just thought, ‘Oh, this will be so fun and lighthearted,'” the former emcee recalled. "But I said, ‘This is great, this will be perfect, this will supersede the jokes, this will loosen everybody up!’” Letterman explained that in his head it was a perfect joke because they had unique names. “Because unusual names — we have three! One of the mistakes that I made was I didn’t tell anybody, ‘Maybe we need a shot of Oprah, maybe we need a shot of Uma, maybe we need a shot of Keanu.’ It never occurred to me." However, he confessed that the audience got confused and the humor did not catch on. 

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