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.

Hollywood was no stranger to employing immigrant talent by this time, and Billy Wilder himself had fled Nazi Europe. Hepburn left Holland for similar reasons. Though many of Wilder's film deal with internationalism, their meanings can be laced with ambiguity, perhaps because of Wilder's own conflicted personal history (his family had died in concentration camps.) These ambiguities echo weightier political and cultural questions.

Smith notes that foreign starlets like Hepburn were celebrated in this time period, but the most famous males were mostly American. Indeed, Bogart was known for his ruggedly American role in Casablanca. This gendering goes back to the reconfiguring of the May-December romance into a symbol for the triumph of American culture in Europe.

Smith traces the history of competition between Hollywood and the French cinema, arguing that the Larrabees' business in Sabrina reflexively mirrors America's "cowboy-style" business tactics. Sabrina's time in Paris teaches her feminine skills that make her attractive for American consumption, and because Sabrina must be out of the way for David Larrabee to marry into the sugarcane business, Linus's courtship with her is originally just another business move for the greater good. When asked why the merger is necessary, Smith quotes Linus, painting America as a postwar savior: "So a new industry goes up in an underdeveloped area and once barefooted kifs have shoes, washed faces, and their teeth fixed." American commodities, as in the Kitchen Debate, came to signify American superiority.

Once Sabrina remakes herself, she becomes an object for men to possess and exchange, sometimes without her knowing it. Smith points to Sabrina's enigmatic and changing class status as a symbol of the promise Americanization would hold for postwar Europe.  Though initially reading a political agenda into this fairy tale story might seem like a bit of a stretch, Smith makes a convincing argument that might apply to many films of the age, when Hollywood was selling not just movies, but the American way of life.

All three versions have the same essential Cinderella story skeleton. The "Cinderella" terminology that is often used in describing them is not quite apt, however, because the character of Sabrina is self-reliant and never depends on a man to save her. How strong she is does vary from version to version, though.

Wood argues that in the original play, Sabrina is autonomous, politically active, and well-educated. She returns from Paris not because she is in love with David Larrabee, but to escape a marriage proposal that she doesn't want to be tied down to. She doesn't need to be rescued, and her relationship with Linus becomes one of mutual companionship. Gender and class issues are sidestepped when Sabrina declares herself as self-supporting and her chauffer father comes into a windfall of money.

In the play's original adaptation for the screen, Wilder and his associates conceived Sabrina as a teenager in puppy love. Though her time in Paris leaves her sophisticated, this Sabrina is not educated or assertive, like her predecessor, and becomes an object to be passed between the Larrabee brothers. She chooses Linus, in the end, because she wanted to care for him. Wood argues that this allows the movie to become "a dark study of gender," because "Sabrina feels strongest when she is helpful to others, when she denies her own needs and desires." Wood refers to the theories of developmental psychologist Nancy Chodorow, which state that while boys develop intimacy problems, girls learn to doubt their identities. This can lead to passivity and vulnerability to manipulation in women like Sabrina.

Wood reasons that the 1995 film version, while not without problems, is instilled with better representations of gender politics. The Sabrina character is in the fashion industry, less domestic than cooking, and while in Paris she "finds herself." This autonomous description is at odds with her actions, though, as she still displays a tendency towards caretaking.

All three versions are at fault because class and gender problems disappear without explanation during the happy ending. The film versions, though, let Sabrina be manipulated by men and lose her own identity.  Wood's analysis of the role of gender in the play and films gives readers a way to understand these ingrained cultural messages, rather than just consuming the film as entertainment.