Jennifer Aniston and Tate Donovan
Credit: FC Jennifer Aniston
Friends co-stars Jennifer Aniston and Tate Donovan dated for three years before getting engaged in 1998. Although their engagement didn’t last very long Donovan continued to play Jennifer’s boyfriend on Friends even after their breakup. “It was horrible. It was so tough. I remember getting back to my dressing room and just weeping,” Donovan admitted in an interview. Aniston went on to marry and then divorce Justin Theroux.