Gabe (Woody Allen) and his wife, Judy (Mia Farrow), are shocked to discover that their best friends, Sally (Judy Davis) and Jack (Sydney Pollack), are splitting up. Not only did they not see the breakup coming, but it makes them start to question their own relationship. While Gabe flirts with the idea of dating one of his college students (Juliette Lewis), Sally and Jack discover that being single again isn't all its cracked up to be and contemplate getting back together.