Oprah Just Revealed the Most "Inappropriate" Question She Ever Asked
Daniel Rodriguez
Updated on February 22, 2026
Oprah Winfrey is one of the all-time best when it comes to conducting interviews, but even she's made her share of mistakes. During an appearance on Rob Lowe's podcast, Literally! With Rob Lowe, Oprah revealed the most "inappropriate" question she ever asked an actor during an interview. The host also said that the question was so bad that her subject completely shut down for the rest of the conversation. Read on to find out which Oscar-winning star Oprah asked an invasive question about her love life and how she reacted.
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Oprah asked an awkward question about Sally Field's relationship.
On Literally!, Oprah said she regretted asking about Sally Field about Burt Reynolds. The actors dated for five years in the late '70s and early '80s, when they were both already famous, so the topic seemed to be fair game. But Field didn't appreciate the specific question that Oprah asked.
"This is when I was younger, and I was not living from the point of view of the surrogate," Oprah said. "But I did feel a responsibility to have to ask the questions that the viewer wanted." So, she went forward with it: "Sally Field was on, my big mistake, I asked her, 'Does Burt sleep with his toupée on?'"
Field "went cold" for the rest of the interview, Oprah said.
Oprah said she lost Field completely after that question. "I cringe to even think that I asked that question," she continued. "But I asked it because the producers are like, 'You have to ask, you have to ask, you have to ask. That's what everybody wants to know.' And so I asked it, and she went cold on me. She shut down, and I could not get in again."
Oprah knows now that her reaction was warranted.
"It was like, 'Whoa, Sally went cold on me on live TV. I deserved it, I deserved it, I deserved it, because that is such an inappropriate question," she said.
Lowe added, "Meanwhile, I still want to know," to which Oprah said, "Well, she certainly didn't answer it."
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Oprah has regretted the direction of that interview for years.
It isn't a new development that Oprah sees the Reynolds question as a mistake. She made reference to it sixteen years ago.
In a 2005 interview with Today, Oprah mentioned the Field interview when asked about a time she crossed the line in her career. "Sally Field used to date Burt Reynolds and I asked this awful question. It was a bad question. I wouldn't do it today," she said. When she was pressed on what the question was and whether it was about sex, Oprah responded, "No, it was worse than that. It was worse than sex … It was a hair question."
RELATED: This Resurfaced Oprah Interview With Mary-Kate and Ashley Has Fans Livid.
Field wasn't so upset that she didn't sit down with Oprah again.
While Field turned cold when asked about Reynolds' hair, she has been interviewed by Oprah again since. Field appeared on Oprah's Next Chapter in 2012, and was interviewed by Oprah for her magazine in 2008. In the 2008 interview, Oprah again asked about Reynolds, but kept her question more appropriate. She asked Field what their relationship taught her about herself.
RELATED: The One Guest Stephen Colbert Never Wants to Interview Again.
Lia Beck Lia Beck is a writer living in Richmond, Virginia. In addition to Best Life, she has written for Refinery29, Bustle, Hello Giggles, InStyle, and more.Read moreFiled UnderCelebrities • Entertainment • NewsRead This NextOprah Had a Pre-Interview Request for Meghan
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