The Handsomest Man chapter opens in Charleston, where life carries on amid the looming Civil War. The Battery, with its lively atmosphere, is filled with carriages, well-dressed women and men, and the occasional cannon blast signaling military readiness. In this charged environment, Mary Chesnut, a well-known figure in the local elite, finds herself at the center of attention due to her flirtation with former Governor Manning. Known for his good looks and wealth, Manning is also married, which only adds to the intrigue. In Southern society, such flirtations were seen as harmless diversions, a way to escape the growing tension of the times and the uncertainties surrounding the nation’s future.

Mary and her husband traveled from their Mulberry plantation to Charleston on March 25, boarding a train full of attendees heading to the state’s secession convention. Manning, ever the smooth operator, managed to sit next to Mary by pretending to act as a guardian to a young lady. Their interaction quickly became a spectacle, as Mary appeared to thoroughly enjoy Manning’s attention, a fact that stirred jealousy in her husband. This subtle yet charged dynamic between Mary and her husband illustrates the complexity of their relationship, set against the backdrop of social expectations and the high tensions of the impending war. The flirtation, lighthearted as it may seem, serves as a window into the undercurrents of Southern society at the time, where public appearances and private emotions were often in conflict.

During their stay at the Gidiere boarding house, tensions arose at breakfast, where her uncle, Judge Withers, made pointed remarks about Mary’s tendency to incorporate French phrases into conversation. This observation led to a witty exchange between the group, with William Henry Trescot quipping about their efforts to keep certain discussions private, so as not to be overheard by the enslaved staff. This moment highlights the social distinctions of the time, where even the simplest conversations were colored by the social hierarchies and expectations of Charleston’s elite. Despite the humor in their conversation, the subtle tension between the old Southern social customs and the emerging new realities is evident.

Manning’s flirtation with Mary continued unabated, and during breakfast, he interrupted her with an unexpected request for a photograph, showcasing the ritualistic nature of social interactions at the time. Dressed formally, Manning’s request was just another expression of the performance that flirtation had become in their society, where appearances and gestures held significant weight. Mary, clearly enjoying the attention, invited her husband along to partake in this charade, which seemed to amuse her. Yet, as the day wore on, the atmosphere shifted. The more somber visit to Magnolia Cemetery with friends introduced a stark contrast to the playful moments of flirtation, reflecting the underlying tensions of the period. In a place where death was often just another part of life, the day’s events seemed to encapsulate the duality of Southern society—caught between the frivolous distractions of social rituals and the ever-present reminder of the war’s shadow.

That evening, the situation came to a head when Mary’s husband confronted her about her attention to Manning. The accusation of flirtation was met with laughter from Mary, who found the suggestion amusing rather than offensive. This reaction hints at the complex dynamics of their relationship, where flirtation, whether genuine or just part of the societal game, was neither taken too seriously nor dismissed entirely. Mary’s laughter underscores a tension in her marriage, one where the boundaries of acceptable behavior were often tested, and the line between social expectations and personal desires was constantly negotiated. The chapter closes on this note of ambiguity, where societal norms, personal desires, and the looming war all intersect, creating an environment of complicated relationships and uneasy compromises.