Christina Applegate
These two icons met at barbecues on the set of “Married … With Children” when Applegate was just a teen, and there are several photos of them getting cozy at different events, including the 1989 MTV Movie Awards, where he was her date. Like Schoelen, she left him for another man. She won’t reveal who it was, but she did say on Andy Cohen’s “Watch What Happens Live” that she never dated Pitt again after the incident.
Juliette Lewis
These actors dated for about four years starting in 1980 and also costarred in the movies “Too Young to Die” and “Kalifornia.” Years after breaking up, Pitt told Vanity Fair that he still loved her, calling her a genius and saying it was one of the “greatest relationships” he’s ever been in. The two are still friendly, but Lewis doesn’t like being asked about her relationship with the megastar, saying that she’s often asked about Pitt or her former drug addiction.
Jitka Pohlodek
Brunette beauty Jitka Pohlodek was a model that Pitt dated in the 1990s and whom he brought to the premiere of “Legends of the Fall” in 1994. They’ve both been hush-hush about their brief relationship, but Pohlodek told PEOPLE in 2000 that “the man glows,” even though he had told Vanity Fair then that he still loved Juliette Lewis.
Gwyneth Paltrow
Paltrow and Pitt met on the set of the 1995 thriller Se7en, and the actor called her the love of his life in his 1996 Golden Globes acceptance speech. They got engaged in December 1995 but split up in 1997 before getting married. According to her episode on the podcast Call Her Daddy, Paltrow wasn’t ready for marriage, but they remained friends. On the podcast, she called it “major, major love at first sight.”
