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And this wasn’t the first time Letterman made Aniston visibly uncomfortable. In a now-infamous 1998 interview, he grabbed her neck and sucked on a strand of her hair. Aniston, visibly uneasy, wiped her hair with a tissue Letterman handed her.
He then handed her a tissue to wipe off the saliva, adding to the awkwardness of the exchange.
Aniston handled it with grace, as she has so many times throughout her career. Known for maintaining her composure no matter the situation, she managed to keep the conversation going.
Even after such an uncomfortable moment, she later returned to The Late Show, proving once again that she could rise above even the most awkward encounters.
Two years after her infamous ”leg” moments with Letterman, Jennifer Aniston returned to the show, this time wearing a chic pink party dress that once again reminded viewers just how stunning she was.
Images from the clip have gone viral on social media recently, but most people seem to focus on Jennifer’s legs and overlook what she’s actually holding in her hand.
Because this time, the Hollywood icon had more than just her looks on display. While the actress was busy trying to dodge personal questions, including one about her relationship with John Mayer, she also took a moment to present the host with a thoughtful gift.
Aniston, who had graced the cover of GQ wearing nothing but a red, white, and blue necktie, presented the gift to the Late Show host while promoting her new film Marley & Me.
“It’s an early Christmas present,” she said with a smile.
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.
When the tie
appeared a little too short, Letterman quipped, ”You know what they say about guys with short ties.”
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.