Max Shulman and Robert Paul Smith's Broadway hit The Tender Trap is transformed into a beguiling Frank Sinatra film vehicle. Sinatra plays a Manhattan showbiz agent, Charlie Y. Reader, who enjoys the attentions of several willing young ladies. At an audition, Charlie meets aspiring actress Julie Gillis (Debbie Reynolds), who is so determined to land a husband that she's already set the date. She goes out with Charlie for a short while, then announces that she won't marry him until he gives up all his other girls. Charlie, who hasn't said word one about marriage and who'd been preparing to give Julie the brush-off, is startled by her ultimatum -- so much so that he genuinely falls in love with her, which (we can safely assume) was her intention all along. A complication involving Charlie's former amour Sylvia Crewes (Celeste Holm) and his best friend Joe McCall (David Wayne) paves the way for the film's slightly offbeat denouement. In addition to scoring at the box office, The Tender Trap yielded a hit song (written by Sammy Cahn and Jimmy Van Heusen), which would remain a part of Frank Sinatra's repertoire for the rest of his life.