Few images so perfectly capture the social rituals of the Gilded Age as One difficulty of the game by Charles Dana Gibson, the celebrated American illustrator whose "Gibson Girl" became an icon of turn-of-the-century femininity. This drawing is one of the most reproduced works in popular magazines of its era, frequently cited in discussions of how Gibson's witty observations shaped public perceptions of gender roles. Its title, often referenced in contemporary reviews, hints at the subtle, often comic obstacles faced in the genteel sport of courtship. Set in a genteel drawing room, the scene shows a young woman and a man engaged in a parlor game—perhaps charades or a card game—yet the real contest is one of glances and gestures.

The woman, poised and self-assured, appears to have the upper hand, her posture both inviting and elusive. The man, slightly awkward, leans forward in anticipation, his body language betraying uncertainty. Gibson’s crisp pen lines and careful attention to costume and expression highlight the tension between decorum and desire.

Unlike the more sentimental renderings of courtship by Norman Rockwell a generation later, Gibson’s work sparkles with irony and a sense of social satire. The precise date and medium of One difficulty of the game remain uncertain, as is often the case with Gibson's prolific output for periodicals like Life and Harper’s Weekly. Originally created for mass reproduction rather than gallery display, the drawing has circulated widely in print, making its original sheet difficult to trace. Today, examples of this work can be found in both private collections and major institutions, including the Library of Congress.

One difficulty of the game stands as a testament to Charles Dana Gibson’s keen eye for the subtleties of social performance, and it remains a favorite among collectors of American illustration.