‘The Tender Trap’ (1955)

Frank Sinatra played a theatrical agent who falls for a young actress, played by Ms. Reynolds, in this romantic comedy directed by Charles Walters. (“Debbie Reynolds is all cuteness and spunk,” wrote Bosley Crowther in his review.) In a 2013 interview with NPR, Ms. Reynolds, who was married three times — including to the singer Eddie Fisher — said she received some relationship advice from Sinatra: “He said: ‘Now, I know you’re engaged to Eddie, but I don’t want you to marry a singer, because none of us are faithful, and he won’t be, and I’m not. We’re just awful,’ he said, ‘so don’t do it.’ And of course I didn’t mind him, and I had a lot of problems because I didn’t mind him, but Eddie and I were very young and very much in love at the time, but I guess he falls in and out of love.”