Christina Applegate: The Beginning

His age: 26

Duration: 1989

Brad Pitt’s connection with actress Christina Applegate traces back to their teenage years, as they frequented barbecues on the set of Married … With Children, where Applegate was a cast member.

Their interactions at these gatherings sparked rumors of a budding romance. The pair were often photographed getting cozy, including at an Amnesty International event in 1988. Pitt even accompanied Applegate as her date to the 1989 MTV Movie Awards, reflecting the depth of their friendship and potential romantic interest.