Tate Donovan had tough experience working with his ex Jennifer Aniston on "Friends". This is because he had to act as Jennifer Aniston's character Rachel's crush and as the first guy that she ever asks out but in reality, both of them were dating for two years.
He recalled, "The producers came to me and said, 'Hey, we want you to do a five-episode arc where you guys are dating and you’re not really that into her.' And I was like, 'Oh, so you’re gonna do that thing.'"
He then continue, "We were just breaking up and I, for some weird reason, thought that maybe working together would ease the breakup. Maybe we’d become friends quicker. I just wanted to go gently into the good night – we both did."
"It was very tough. Everyone was so supportive, but it was hard. It’s like going to class when you’re in high school and you’ve broken up with the girl who you sat next to and… it’s tough".