The Tender Trap (1955) is a comedy starring Frank Sinatra, Debbie Reynolds, David Wayne, and Celeste Holm. Based on a 1954 play The Tender Trap by Max Shulman and Robert Paul Smith, "The Tender Trap" marked Sinatra's return to MGM. some six years after On the Town, although his second film under a new contract with the studio, Guys and Dolls, was released ahead of "The Tender Trap" by one day on November 3, 1955. The film was nominated for the 1956 Academy Award for Best Original Song, for the song "(Love Is) the Tender Trap" (music by Jimmy Van Heusen and lyrics by Sammy Cahn). The song proved a hit for Sinatra, which he would continue to sing throughout his career.
Charlie's best friend, Joe McCall (Wayne), who has a wife and children in Indianapolis, is visiting New York and staying at Charlie's apartment. He begins to fall in love with Sylvia (Holm), a former lover of Charlie's. Sylvia is approaching 33 and believes Charlie is her last hope of getting married. She is thrilled to have Charlie propose to her, only to discover at their engagement party that he has proposed to Julie as well.