In the late 1980s and early 1990s, Pitt was involved in successive relationships with several of his co-stars, including Robin Givens (Head of the Class), Jill Schoelen (Cutting Class), and Juliette Lewis (Too Young to Die? and Kalifornia).
Pada akhir 1980an dan awal 1990an, Pitt terlibat dalam hubungan berturut-turut dengan beberapa lawan mainnya, yang meliputi Robin Givens (Head of the Class), Jill Schoelen (Cutting Class), dan Juliette Lewis (Too Young to Die? dan Kalifornia).