Night Out With Famous Friends (1988)
Pitt together with Christina Applegate at an event by Amnesty International. This summer evening would not be the last big night out they had together.
Big Heartbreak (1989)
Pitt and Schoelen got engaged in 1989, but it just lasted three months. Pitt revealed in a 2011 interview that he went to Budapest to visit his then-fiancée while she was shooting a film. When he got there, Schoelen admitted she had fallen in love with her movie’s director and she and Pitt called it quits. According to Pitt, his first big heartbreak was Schoelen.