Jennifer Aniston Once Dated Her On-Screen Brother Charlie Schlatter

Jennifer Aniston's love life has been a topic of interest throughout the years. However, likely her most notable relationship was with Brad Pitt. The pair wed in 2000, though they split in 2005 after rumors swirled about an alleged affair between him and Angelina Jolie. She would say "I do" again in 2015 to actor Justin Theroux, though this relationship was also short-lived, with the couple splitting two years later. While both marriages, which Aniston doesn't view as failures, were highly publicized, one of Aniston's lesser-known courtships before she became a wife was with Charlie Schlatter.

The pair met on the set of NBC's sitcom, "Ferris Bueller," where Schlatter played the leading role, while Aniston portrayed his big sister, Jeannie. The series was short-lived, only surviving one season. During that time, Schlatter and Aniston developed a romance, even walking the red carpet in a coordinated denim look. However, just like their show, the relationship doesn't appear to have lasted long.

When "Ferris Bueller" was being filmed, fans were unaware that the show's star, Charlie Schlatter, was dating Jennifer Aniston. However, those who worked on the set were well aware. Their young fling was brought to light in April 2014 when GQ's Editor-in-Chief, Jim Nelson, reminisced about his time as a celebrity assistant in a culture piece titled "The Horrible Bosses of Hollywood." Nelson broke the news that Aniston and Schlatter were an item during filming, which many saw as a good thing.

"Everyone on set thought she was hot, including Schlatter, with whom she had a brief, torrid romance—while playing, it must be said, his older sister," Nelson wrote. While Aniston has never commented on this alleged boyfriend, during a 1990 interview with Waterloo Region Record, she praised the off-camera relationship she shared with her fictional brother and the many other actors who brought "Ferris Bueller" to life, sharing, "We love doing this show. From the time we made the pilot, we were getting along very well." [via Catchy Comedy].

"Ferris Bueller" wrapped in 1991. Unfortunately, the series only got 13 episodes and was not renewed. After the show ended, it also seems like the flame fizzled out between Jennifer Aniston and Charlie Schlatter. The following year, he met and began dating publicist Colleen Gunderson. The pair got married in 1994 and have remained together since then, welcoming three children.  He and Aniston haven't talked much about one another once the show ended, seemingly leaving their quick relationship in the '90s.

Aniston is not even interested in rekindling their professional association. When asked about a possible reunion of the show, Aniston told Access Hollywood in 2019, "That would be a really, absolute no." Instead, she has moved on to other popular films such as "The Switch" and "Horrible Bosses." Though there isn't a chance for the two to reconcile, their brief relationship is undoubtedly a notable pop culture moment in Aniston's dating history.