Some of the reason for the May-December theme had to do with casting, and were not originally intended. In Sabrina, the role of Linus Larrabee was originally meant for Cary Grant, so when it went to Humphrey Bogart, a man much older than Audrey Hepburn, the role took on new layers of meaning. Linus came to be seen additionally as a father figure to Hepburn's young Sabrina. Casting Gary Cooper opposite Hepburn in Love in the Afternoon yielded similar results, as did choosing the iconic Marilyn Monroe to portray what had been a more average role on the Broadway stage in The Seven Year Itch. But Dick also tries to connect this motif to a theme or motivation in Wilder's life. He notes that Wilder's age when he was working on these movies might have affected his outlook. In middle age, the theme of rejuvenation may have been of particular interest to him, and the fatherly relationships may have reflected his own love for his daughter at the time.

In Sabrina, Dick sees one father-daughter bond being replaced with another, the first biological, the second metaphorical. Dick argues that in her relationship with Linus, Sabrina re-channels the love she used to reserve for her father towards her beau. Linus provides financial security and protection for Sabrina, just as a father would. This situation is only believable because the film operates as a fairy tale, Dick says.

Grouping these films together is interesting, but from the descriptions of Love in the Afternoon and The Seven Year Itch, it doesn't seem that the films have as much in common with each other thematically (aside from romance) as Dick might have us believe. And some of what they do have in common, as Dick admits, has do with coincidences of casting. This grouping seems to serve best simply as a way for Dick to organize Wilder's many films.