Wow! It turns out Jon knew Jen WAY before she became a huge movie star!

When Jennifer Aniston sat down with Jon Stewart on Aug. 19 to plug her new movie, The Switch, the promotional interview on The Daily Show quickly took a sharp turn into a trip down memory lane! Jon reminded Jen of a circa mid-90s dinner date they went on to a New York City Italian restaurant, when Jen was, as Jon describes her, “a young ingenue” starting out on the soon-to-be TV mega-hit Friends.

Appearing fit and healthy in a short sleeveless dress and heels, Jen discussed the “date” she went on with Jon and they each had very different versions of the story. Jon joked that the fine-dining loving actress “brought so many” of her friends to their “date,” which Jen recalls was not exactly a full-fledged “date.” Jen remembers that Jon’s invite was more along the lines of “Hey, a group of us are going out, do you want to join?” Hmmm, seems like this was doomed from the beginning with their major lack of communication!

Although this interview got awkward, Jen quickly transitioned into talking about her love for New York City, where she says she still “wishes” she lived. It might be uncomfortable talking to an old flame, but thank goodness she didn’t have a repeat of her “Regis and Kelly” interview where she used a VERY inappropriate word and got flack from the Special Olympics for her serious faux pas!