David Letterman’s question that left Jennifer Aniston very uncomfortable
Letterman wasted no time in taking off his current tie and putting on the new one with Aniston’s help. She handed him the Brooks Brothers tie she wore on the cover of GQ magazine, saying, “This is a highlight of my career.” Letterman, wearing the tie with pride, joked, “Funny, the tie said the same thing during the photoshoot.”
”This is exciting, I’m dressing Dave!” she exclaimed.
It was a playful moment, and fans couldn’t help but gasp at the surprising gesture.
While Aniston has never spoken out against these encounters, looking back, it’s clear these moments haven’t aged well. What was once dismissed as late-night humor is now sparking a new conversation — one that’s hard to ignore.
