Jennifer Aniston is no stranger to the spotlight, but not all of her public appearances have been smooth sailing. One particularly uncomfortable moment occurred during a 2006 interview on The Late Show with David Letterman. While promoting her film The Break-Up, Aniston found herself in an awkward situation that has since become a talking point.
The interview took a strange turn when Letterman began fixating on Aniston’s legs. Dressed in a stylish black outfit with shorts, Aniston received repeated compliments from Letterman about her legs. “You have amazing legs,” he said, even prompting the cameraman to zoom in on them. Aniston, visibly uncomfortable, tried to laugh it off, but Letterman continued to bring up the topic, leaving her squirming.
The awkwardness didn’t end there. Letterman shifted the conversation to Aniston’s rumored relationship with co-star Vince Vaughn, asking if Vaughn had suggested she appear naked in the film. Aniston, caught off guard, handled the question with grace, redirecting it back to Letterman.
This wasn’t the first time Letterman made Aniston uncomfortable. In a 1998 interview, he grabbed her neck and playfully sucked on a strand of her hair, leaving her visibly unsettled. Despite these moments, Aniston remained composed, showcasing her ability to navigate challenging situations.
Years later, Aniston returned to The Late Show, this time gifting Letterman a tie she had worn on the cover of GQ magazine. The gesture turned the interaction into a lighthearted moment, but the earlier incidents remain a topic of discussion. While some view these moments as harmless late-night humor, others see them as examples of behavior that hasn’t aged well.
