It wasn’t their first awkward moment. In a 1998 interview, Letterman stunned viewers by grabbing Aniston’s neck and sucking on a strand of her hair. She pulled away, clearly unsettled, while he handed her a tissue. The clip resurfaced in 2021, reigniting outrage and disbelief. Despite such incidents, Aniston continued to appear on The Late Show, always handling the situations with grace.