The play follows Alan and Buddy Baker, brothers who have decided to leave their family's waxed-fruit business and experience the good life. In the beginning of the play, Alan is a typical ladies' man, and his younger brother is a 21-year-old virgin. As the play progresses falls in love with Connie, one of the girls that he is sleeping with, and when she leaves his life, he falls apart. While Alan mourns the loss of Connie, Buddy becomes a ladies' man himself.
The play was made into a movie, with a screenplay by Norman Lear, starring Frank Sinatra as Alan, Lee J. Cobb as his father Harry, and Barbara Rush as Connie. Alan's conflict over whether to lead a carefree bachelor lifestyle, or to settle down with Connie, has been seen as reflecting the social tensions of the early 1960s.