Marilyn Manson
Manson first met Evan Rachel Wood when she was barely 18 years old. Despite Manson’s marriage to Dita Von Teese, they dated and remained together following Manson’s divorce. They finally were engaged, but they decided to call it off before getting married. Wood told Rolling Stone that she hadn’t realized she was gay at the time, which led to their separation.

Dean McDermott
McDermott was married to Mary Jo Eustace at the time he began work on the television film Mind Over Murder. He met and began dating co-star Tori Spelling here. They both divorced and married their separate partners. McDermott later cheated on Spelling, claiming on True Tori, “Dean and I met while we were both married to other people, so now that this has happened to me, I know a lot of people are thinking, ‘Well, karma’s a b*tch.'”