#4: Charlie Schlatter: The Beginning

Her age: 21

Duration of Relationship: 1990

In 1990, Jennifer Aniston starred in NBC’s sitcom Ferris Bueller, based on the hit movie Ferris Bueller’s Day Off. Aniston played Jeannie, the titular character’s sister, portrayed by Charlie Schlatter.

The show, which ran for 13 episodes, brought the two young actors together on set, sparking a connection that extended beyond their on-screen roles. The chemistry between Aniston and Schlatter quickly blossomed into a brief but passionate romance.