Charles Ruggles was nominated for the 1959 Tony Award (New York City) for Supporting or Features Actor in a Drama for "The Pleasure of Your Company" and recreated his role in the movie version.
Designer Edith Head appears in the opening scene of the movie (one of a select few appearances in film) directing alterations to Jessica's wedding dress at I. Magnin & Company, a luxury department store in San Francisco, California.
The original Broadway production of "The Pleasure of His Company" opened at the Longacre Theater in New York on October 22, 1958 and ran for 474 performances. Samuel A. Taylor wrote the stage play with Cornelia Otis Skinner and wrote the screenplay for the movie version. The play received four Tony Award nominations, winning one for acting.