Diane Keaton, Age 74 – Single

We’ve already talked briefly about the icon that is Diane Keaton, in regard to her relationship with Al Pacino. However, despite having a taste for tough guys, she also has a soft side, proven by her relationship with Woody Allen and Warren Beatty in the 70s.

She met Woody in an audition of a Broadway production of his and fell for his quirks and humor. They collaborated on 8 films in that era, and even though they didn’t last romantically through time, they’re still friends. Same happened with Beatty too, as they were already dating by the time Reds was being filmed. However, they ended their relationship shortly after the film was done.