Before Brad Pitt and before the endless speculation on her love life by the tabloids, Jennifer Aniston passed on the chance to become gossip fodder with none other than The Daily Show host Jon Stewart. Unfortunately for celebrity watchers, their one date back in the 1990s didn’t go anywhere.
Jennifer Aniston and Jon Stewart discussed their ill-fated date when she came to The Daily Show with Jon Stewart to promote her new movie The Switch.
According to Jon Stewart, he asked Jennifer Aniston out on a date, but, much to his disappointment, she brought along several of her friends. He recounted her rejection saying, “Here’s what was nice about it that I remember: You brought so many of your friends. And I remember thinking, well she’s so excited about being on a date with me she wants me to get to know her posse.”
Jennifer Aniston, on the other hand, had a fuzzy recollection of it being a group outing from the get-go. Even though she admitted she may have been remembering incorrectly, she defended herself stating, “It’s unclear, but it just shows my commitment to friends.”
Had she known Jon Stewart would become one of the most respected fake newsmen around, Jennifer Aniston might have taken a different approach to their long ago date.