Jennifer Aniston and Jon Stewart once had such an awkward date that the talk show host couldn't help but bring it up as soon as she joined him on "The Daily Show" in 2010 — despite the fact that it had happened over a decade earlier. In front of the cameras, Stewart humorously recounted inviting Aniston to a romantic rendezvous during the first season of "Friends." However, upon arriving at the Italian restaurant, the talk show host quickly realized a miscommunication had occurred as Aniston was accompanied by a group of friends.
He quipped, "And I remember thinking, 'She's so excited to be on a date with me, she wants me to get to know her posse.'" Regrettably, for him, the TV star's intention was a group hangout, not a one-on-one date. Aniston jokingly responded, "It shows my commitment to 'Friends.'" While it's unclear how exactly things got going between Aniston and Stewart, their flirtatious dynamic was captured in a 1995 interview.
During Aniston's appearance on "The Jon Stewart Show," the doomed couple displayed evident fascination with each other. Upon sitting down, Stewart playfully put his arm around Aniston as he stretched, after which she complimented the comedian's eyes and even told him he was cute. There's a strong possibility he asked her out afterward, and one can only hope it went more smoothly than their awkward date.
