This article uses love letters to investigate matters of intimacy and affection in extramarital affairs. Two women committed adultery with a missionary and a governor in Spanish San Antonio. Their missives reveal how they circumvented restrictions and carved out a space for love outside their marital beds. The drama that unfolded after a political vendetta terminated the relationships exposes this community’s posture regarding “illicit” sexual liaisons. It confirms that in this frontier region local customs allowed greater tolerance concerning expected gender roles and behavior when compared to other areas of Spanish America. These missives, preserved as evidentiary material in the trials, also reveal important clues about access to literacy and the networks that assisted letter writers in sustaining their extramarital unions.