Overanxious film critic Allan (Woody Allen) sinks into a depression after his wife leaves him. Concerned, his married friends Dick (Tony Roberts) and Linda (Diane Keaton) encourage him to meet new women. Inspired by Humphrey Bogart's dark persona, Allan attempts to emulate him in flirting with women. However, his frail personality ensures that his every attempt blows up in his face. His hapless romantic life reaches catastrophic levels when he develops feelings for Linda.