Since medieval European iterations of the romance genre, the May-December romance has proven a popular trope. It generally refers to the love between a young, innocent woman and much older man. Typically, the age difference is seen as a problem, and sometimes the trope is used satirically to suggest that the older man, in the later seasons of his life, has been duped by lust for an ambitious young woman who encourages his suit to achieve higher status or other benefits. A famous example of such a romance is “The Merchant’s Tale” in The Canterbury Tales (1392) by Geoffrey Chaucer. In this story, the young wife, May, deceives her much older and blind husband, Januarie, by dallying with her lover in a pear tree inside the garden that Januarie has built to both enclose and protect her. The Second Mrs. Astor subverts this trope by showing that Madeleine and Jack, despite the assumptions and judgments made about them based on their age difference, are truly in love.

The difference in their ages provides much fodder for the tabloids in The Second Mrs. Astor. Jack is 29 years older than Madeleine, and the age gap is exacerbated by Jack’s celebrity and his descent.