The Tender Trap (1955)

Womanizing theatrical agent Frank Sinatra’s idyllic life is disrupted when he falls for young actress Debbie Reynolds who has her entire life mapped out, starting with getting married by her next birthday. Sinatra’s role here reminds me a lot of his character in Come Blow Your Horn and a lot of the same criticisms hold true, though he’s not quite as old in this film. Reynolds is adorable, but her character is at best exceptionally naïve and there’s little reason for the two of them to get together. Celeste Holm, as one of Sinatra’s many girlfriends, is a highlight as the most sensible and put together character in the entire film.  

Oscar Nomination: Best Music, Original Song