In their published memoirs of the Peninsular War, a surprising number of British officers mentioned visits to Portuguese convents and openly confessed to having flirted with the sisters – occasionally to the point of outright seduction – and abandoned them when the regiment moved on. This seems like a very negative self-fashioning to modern readers, but can best be understood in the context of the political and cultural climate in which these memoirs were produced. This article argues that officers' descriptions of convent visiting and their professions of sympathy for cloistered women revealed the influence of gothic, erotic, romantic, and travel literature on military life writing. Their depiction of nuns differed from nuns’ portrayal by common soldiers due to its infusion with masculine ideals of chivalry and sensibility. Elite memoirists saw no need to justify their abandonment of nuns because they viewed it in light of other literary accounts of soldiers who broke nuns’ hearts. At the same time, they contrasted themselves with the barbarism of the French, believing themselves to be far more compassionate and tolerant of Catholic strictures. Officers’ portrayals of Portuguese sisters can thus also be seen as an expression of Britons’ sense of their relationship with Portugal in the war.