Brad Pitt

Although his handsome features and irresistible charm didn’t catch the public’s attention until his role in the 1991 film Thelma & Louise, the Hollywood sensation was already a fixture in the industry dating pool long before then. While fans are well-versed in the specifics of Brad’s marriages to Angelina Jolie and Jennifer Aniston, he got involved with other celebrities in his younger years.

Brad was linked to Sinitta, a British-American singer, whom he dated for two years in 1984. The singer later revealed that the young Brad was sweet and charming when they were together. After a series of brief relationships with co-stars, he got engaged to Jill Schoelen and Gwyneth Paltrow, but both didn’t push through. Although his marriages with Jennifer and Angelina did not end successfully, Brad is regarded as one of Hollywood’s most eligible and richest bachelors, with a long list of flames and investments to prove it.