Annie Hall (1977)
Stars: Woody Allen, Diane Keaton
Like many great romances, Annie Hall is deceptively simple: cynical comedian muses over his failed relationship with a woman who was far too free-spirited for him to ever keep up with.
But don't count this out as your typical rom-com—the fast-talking Woody Allen-directed flick depicts romance, love, and broken-in relationships as they are, all against the picturesque background of Manhattan. Don't count on this to turn you into mush; instead, you both could be basking in some intellectual stimulation.