Brad and Christina briefly dated in 1989. They looked like a match made in heaven until the “Married With Children” star until they attended the MTV Movie Awards together later that year. Applegate ended up ditching Pitt halfway through the Award show to spend time with Sebastian Bach.
Still a relatively low-key name in Hollywood, 27-year-old Brad began a relationship with his “Too Young to Die?” costar, Juliette Lewis, who was 17 at the time. The couple was together from 1989 to 1993, and Lewis has nothing but nice things to say about the relationship. In 2010 she revealed, “I was a teenager at the time. It’s a lifetime away. I was in my high-school years, and it was a wonderful, loving relationship with a fun, smart guy. Then it was over, and he went on to become incredibly famous.”
“Thelma & Louise” costars Brad and Geena only officially started dating a year after production on the movie had wrapped. Though Brad’s former roommate, Jason Priestley, told “The Hollywood Reporter,” Geena, who was much more famous at the time, made sure all of their meetups were done discreetly.
Brad and Gwyneth dated between 1994 and 1997 meeting on the set of the thriller “Se7en.” Their relationship was notably public. Brad proposed in 1996 and referred to Gwyneth as “the love of my life” in his acceptance speech at the Golden Globes that same year. Sadly, they called off their engagement only seven months after Pitt proposed.
Rumors of Brad and Sienna’s romance began in April 2017, after the two were spotted talking to one another most of the night at a “Lost City of Z” dinner in Los Angeles. After the event, the two were spotted spending time together, though neither party has ever confirmed the relationship.