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.