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

When Trevor Noah dated "Friday Night Lights" star Minka Kelly, he wasn't the first host of "The Daily Show" to get a shot at love with a popular television actor. But when his predecessor, Jon Stewart, tried to be more than "Friends" with Jennifer Aniston, no love connection was made during their one-time outing.

The man who turned lampooning American politics into an art form actually interviewed America's sweetheart before "The Daily Show" existed. In the '90s, Stewart hosted "The Jon Stewart Show," which aired on MTV before moving to syndication. Aniston was one of Stewart's guests in 1995, and their interview veered off course almost immediately after she sat down. Stewart slid over the side table separating their chairs, pretended to yawn, and casually placed his arm around Aniston's shoulders. She was a good sport about Stewart shooting his shot for laughs, and even interrupted his questions about her familial showbiz connections [1:21] to exclaim, "You're so cute!" Stewart's response, an awkward joke about making out with her during the commercial break, still wasn't enough to make her roll her eyes. In fact, she continued, "Look at your eyes! Beautiful eyes." Poor Stewart was clearly a little flustered over the unexpected turn of events, cracking another joke about his peepers being implants.

Aniston's comments inspired a new line of questioning about the actor's dating habits, and unbeknownst to her and Stewart, would result in an awkward interview half a decade later.

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."

Although Jon Stewart struck out when he asked Jennifer Aniston out after their 1995 interview, she kept returning to "The Daily Show" to chat with the comedian. She even paid him a sweet compliment in 2015 when he was lamenting his fading youth. "You look the same — except for some little salt-and-pepper, silver fox thing happening — as you did 20 years ago," she sweetly said.

By that time, Aniston had married and divorced Brad Pitt and dated a number of other entertainers, including Vince Vaughn, John Mayer, and then-fiancé Justin Theroux. As for Stewart, he'd been married to his wife, Tracey McShane, for about 15 years. The couple shared their love story with "O Magazine" in 2005. "It's a fairy tale from my end," said McShane. She recounted how she was feeling down after the end of a long-term relationship, which spurred her kind-hearted friends to set out on a mission to help her find Mr. Right. "After a bad date, they'd ask, 'What are you looking for?'" she recalled. "I had discovered 'The Jon Stewart Show,' so I said, 'Someone funny and sweet, like Jon Stewart.'" The comedian serendipitously dropped by a film set to see a friend, and McShane's roommate just happened to be working on the same project. The roomie did such a wonderful job hyping McShane that Stewart agreed to go on a blind date with her. And this love story is our moment of Zen.