Jennifer Aniston And Jon Stewart Went On One Date (& It Was Extremely Awkward)

Jon Stewart learned that Jennifer Aniston dislikes fishing but isn’t opposed to camping as he fished for details about what it takes for a date to impress her on “The Jon Stewart Show.” At some point, he even gathered up the courage to ask Aniston out. (This didn’t happen during their flirty interview, unfortunately.) They reminisced about the outing in 2010 when Aniston appeared on “The Daily Show,” and their exchange became a sitcom plot when they remembered it differently.

According to Stewart, he invited Aniston out to dinner at an Italian eatery in NYC. “It was lovely,” he recalled. “You brought so many of your friends. And I remember thinking, ‘She’s so excited to be on a date with me, she wants me to get to know her posse.'” Aniston replied, “That’s really sad.” Ouch! 

In her version of events, Aniston thought Stewart was inviting her to hang with a group of pals — you know, kind of like a casual, Central Perk sitch, but with bellinis and booths instead of couches and coffee. “It shows my commitment to ‘Friends,'” Aniston quipped. Unfortunately for the actor, comedy wasn’t getting her out of the awkward convo that easily. Stewart kept giving her a hard time by jokingly asking her if she wanted to invite any other people to join them for the interview. But he added, “You were lovely then and lovely now.”

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