Brunette beauty Demi Moore is one of Hollywood’s most iconic actresses. She was the highest-paid female star in the mid-1990s, and her rise to fame began in 1985 when she landed the role of Jules in “St. Elmo’s Fire.” It cemented her as a member of the Brat Pack in the 80s, and while some members of the Pack struggled with their careers as they got older, Demi would continue to thrive, taking on roles in movies like “Indecent Proposal,” “G.I. Jane,” and “A Few Good Men.” She did take a step back for a time to focus on raising her three kids, and at one point, the public became more obsessed with scrutinizing her romantic life than her acting chops. Here are all the relationships Demi Moore has been in over the years.

Tom Dunston

When she was just 15, Moore started dating the 28-year-old Tom Dunston, around the same time she was dealing with a toxic personal life at home. Though problematic now, Moore wrote in her memoir, “He was an attractive 28-year-old with a gentle presence. He immediately made me feel at ease.”

Freddy Moore

Moore had a thing for older musicians and moved on from Dunston with another named Freddy Moore. The guitarist started dating her when she was 16 and he was 29. Another red flag? He was married? That said, they continued seeing each other and ultimately married, though the marriage was short-lived. They were together from 1980 to 1985, but she kept his last name.

Jon Cryer

These two were lovey-dovey co-stars on “No Small Affair,” and their chemistry carried over into real life. Though they dated, Cryer was always more committed to the relationship and admitted that he once came over to her place, where the housekeeper said he was with another man. Moore believed she took his virginity and admitted in her memoir that she was callous with his feelings, but Cryer said he actually lost his virginity in high school.