Woody Allen and Diane Keaton
Characters: Allan Felix and Linda Christie
Movie: Play It Again, Sam (1972)
If there wasn't a whole stack of movies focused almost exclusively on Woody Allen being in relationships, we might never have been to able to picture him dating a woman. Especially a hot one.
Diane Keaton and Woody Allen first met when he cast her for his Broadway show, Play It Again, Sam. In the film version of the play, Keaton's Linda and her husband are friends with Allen's character, Alan, who is going through a divorce. The affair between Allan and Linda is inevitable. After all, who is Woody Allen to deny himself a little bit of on-screen fun?
Despite staying together for only a year, Allen and Keaton continued to work together on movies and remained friends...even after he married his ex-partner Mia Farrow's adopted daughter.