Dearest Hugh offers a window into courtship during the early twentieth century through a collection of three hundred love letters exchanged between Gabrielle Drake and Hugh McColl from 1900 to 1901, illustrating the hopes and sacrifices of an upper-class couple forging a marriage in a small southern town.A resident of Bennettsville, South Carolina, Hugh McColl enjoyed the social status that came with being the son of the president of the Bank of Marlboro. The daughter of the clerk of court for Marlboro County, Gabrielle Drake was a new graduate of Converse College who was then teaching at Bennettsville Graded School. The couple became engaged in May of 1901 and wed that November. Although most of their interactions were chaperoned, Hugh and Gabrielle could speak more freely in their correspondence and exchanged notes - often two or three a day - detailing their private emotions, desires, and anxieties. The letters address equality within the relationship, Gabrielle's career, choosing furnishing a home, and allocation of household chores.Hugh's letters are earnest, sincere, affectionate, and sometimes suggestive. Gabrielle's writings are coquettish and playful, but she also anguishes over choosing between a career and a spouse. The attitudes expressed by both Hugh and Gabrielle also speak to the ambitious drive and community-minded dedication the McColls would later instill in their family, including grandson Hugh McColl, the former president and CEO of Bank of America.Hurley's introduction places the correspondence into the broader context of recent scholarship on courtship rituals and the changing educational and social status for women during this time in American life.