10. Ellen DeGeneres and Anne Heche
Couple Nickname: None
Dated Between: 1997 - 2000
Ellen DeGeneres is in the most adorable relationship ever right now with wife Portia De Rossi, but back in the late '90s, she had a highly-publicized relationship with actress Anne Heche. The two dated seriously for three and a half years, but broke up around the time that Heche realized the relationship was negatively affecting her career.
Heche proceeded to have a breakdown that involved wandering around Fresno, CA barely clothed and calling herself an alien, before she was hospitalized. The actress has since claimed that she "changed her mind" about being gay, and that the breakdown was caused by mental illness she struggled with due to her father sexually abusing her as a child.