Jennifer Aniston has had her fair share of memorable moments in the public eye, but not all of them have been positive. One particularly awkward encounter took place during a 2006 appearance on The Late Show with David Letterman. While promoting her film The Break-Up, Aniston found herself in an uncomfortable situation that has since resurfaced, sparking fresh conversations.
The interview took an unexpected turn when Letterman began focusing on Aniston’s legs. Dressed in a chic black outfit with shorts, Aniston received repeated compliments from Letterman about her legs. “You have amazing legs,” he said, even directing the camera to zoom in on them. Aniston, visibly uncomfortable, tried to laugh it off, but Letterman continued to bring up the topic, leaving her visibly uneasy.
The awkwardness didn’t stop there. Letterman shifted the conversation to Aniston’s rumored relationship with co-star Vince Vaughn, even asking if Vaughn had suggested she appear naked in the film. Aniston, maintaining her composure, skillfully deflected the question, suggesting Letterman ask Vaughn directly.
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 handled each situation with grace, showcasing her professionalism.
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 lightened the mood, but the earlier interactions remain a topic of discussion. While some dismiss these moments as late-night humor, others see them as examples of behavior that hasn’t aged well.
