Jen Aniston & Jon Stewart Reveal Dating Past (VIDEO)

Last night on The Daily Show, Jon Stewart revealed that he and guest Jennifer Aniston used to date. Well, sorta–they went on one date together, but that’s got to count for something, right?

Jen, who was on the show to promote her new film The Switch, apparently went on a dinner date with the adorable Jon back in the mid-’90s when she was just starting out on Friends.

Back in the day, Jen appeared on the network version of Jon’s hit MTV talk show, The Jon Stewart Show, and caught his eye. The comedian asked the young actress on a date, and though she accepted, things didn’t exactly go as planned:

You were adorable […] I asked you out, we went out! To an Italian restaurant. […] And it was lovely, and here is what was nice about it […] You brought so many of your friends. I remember thinking ‘Wow, she’s so excited to be on a date with me that she wants me to get to know her posse.’

Jen said that his re-telling of the story was “really sad” but clarified that she thought the “date” was actually a group dinner, not a romantic private dinner. Oops!

Watch Jon and Jen relive their romantic past below.

The Daily Show With Jon Stewart Mon – Thurs 11p / 10c
Jennifer Aniston
Daily Show Full Episodes Political Humor Tea Party

After their romantic evening, Jen went on to date and eventually marry (then divorce) Brad Pitt and Jon settled down with his wife and started a family. Imagine how different things would have been if these two stayed together!

Do you like the idea of Jen and Jon dating? Let us know what you think in the comments below.

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