Tatum O’Neil

Michael’s first public relationship was with Paper Moon actress Tatum O’Neil. At the time, Michael was 17 and Tatum was 12.

Michael’s split with Tatum, he started dating 15-year-old actress Brooke Shields. The two first connected at the 53rd annual Academy Awards in 1981.

Brooke Shields

Lisa Marie Presley

Michael and Lisa reconnected at a mutual friend’s dinner party nearly 20 years after they first met. While he was overseas on the Dangerous World Tour

Debbie Rowe

Debbie Rowe was the personal assistant to Dr. Arnold Klein, Michael’s dermatologist. Over the years, the two built a friendship that was pretty much platonic.

Debbie agreed to carry Michael’s children as a favor to Michael, and she did exactly that. To put a cherry on top, she ended up marrying her longtime friend.