The question from David Letterman that made Jennifer Aniston uncomfortable

David Letterman is known as one of the longest running talk show hosts in America. While Letterman’s notoriously direct and controversial interviewing style has prompted a number of poignant and hard-hitting questions, it has perhaps more often resulted in awkward interactions for guests and audiences. Letterman even admitted to this interviewing style in 2012, saying, “That’s what I do — I make people uncomfortable!”

Given that Jennifer Aniston has been one of the most celebrated television and film actresses in the world since the mid-1990s, her personal life, with her short-lived marriages to Brad Pitt and Justin Theroux — as well as multiple relationships with co-stars — has taken a lot of interest from many fans noticed in the media. While that might be worth discussing in some interviews, Letterman proved time and time again that when he had Aniston on his show, he tended to go a little too far in his questioning — and flattery — of the actor. Above all, he asked the former “Friends” star one question in 2006, which she also visibly refused.

Jennifer Aniston refused to answer a question about her relationship history

In 2006, Jennifer Aniston appeared on David Letterman’s talk show promoting The Break-Up, a 2006 romantic comedy in which she starred opposite Vince Vaughn (who also co-wrote and produced the film). played the lead role. The interview started on an awkward note when Letterman complimented Aniston on her legs (comments he repeated multiple times throughout the interview) and then began pushing her about whether she was dating Vaughn. Aniston was actually dating Vaughn at the time; They got together in 2005 while filming the film, per People, but would later split in 2006, though she’s clearly been reluctant to talk about it.

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After discussing her legs, Letterman began the interview by asking Aniston if it was Vaughn’s idea to have her “appear naked in the film.” Aniston, nervous at first, responded by telling him he should have asked Vaughn that while he was on the show.

When Letterman went on to say that Vaughn got “all squirrels” when he asked him if he was dating Aniston, she responded by immediately flipping the conversation and asking Letterman about his feud with Oprah Winfrey. After following her on that tangent, Letterman immediately went back to Vaughn, in an exchange that lasted several minutes until Aniston finally asked, “Let’s move on.” In the end, Aniston never answered the question, but made it very clear how uncomfortable she felt.

David Letterman made guests uncomfortable on more than one occasion

Jennifer Aniston’s 2006 appearance on “The Late Show with David Letterman” wasn’t her first appearance on the iconic talk show, nor was it the first time she had an awkward interaction with the host. In 1998, Aniston made her first appearance on Letterman’s show to promote her NBC show Friends. In the now-infamous interview, Letterman spent quite a bit of time talking about her nude experiences in public steam rooms. Then, out of nowhere, he decided to suck on a strand of her hair.

“Forgive me if that’s rude, I just want to try one thing,” he said as he rolled his chair over to her amid a drum roll. Aniston then instinctively backed away, laughing nervously as he opened his mouth and leaned toward her neck. He then grabbed a strand of her hair and sucked it and gave her a paper towel to wipe it off, which she did with visible discomfort. “People are appalled by this,” Letterman said afterwards. “We’ll take it out in the edit, don’t worry.”

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Although Letterman was never charged with sexual harassment, in 2009 he admitted to having affairs with many of his employees. Additionally, over the years, while hosting female guests, Letterman has often engaged in behavior that many interpret as sexual harassment or “abuse.” Aniston has clearly been among those guests on more than one occasion, although she has yet to call Letterman about any abuse she may have felt from him.