In 1940, C.W. Briggs (Woody Allen) is an insurance investigator in New York City who is highly successful, owing to his many connections and ability to think like a criminal. His work does not impress Betty Ann Fitzgerald (Helen Hunt), an efficiency expert who butts heads with C.W. over his old-fashioned views. Her advice is usually followed, however, because she secretly is in a relationship with her boss, Chris Magruder (Dan Aykroyd), who constantly reassures her that they will be free to pursue their relationship in public once he finalizes his divorce with his wife.