In 1613 Paolo Antonio Bon, dragoman of the Dutch diplomatic legation in Istanbul, wrote an incendiary letter to the Dutch States General in which he recounted a tawdry tale of reckless immorality involving the first Dutch ambassador to the Ottoman Empire, Cornelius Haga. This lengthy and highly unusual report provides a rare glimpse into an almost entirely unexplored aspect of early modern diplomacy, the intimate lives of ambassadors and other embassy staff members. It also reveals the political and social ramifications that cross-cultural sexual activity could have on early modern diplomacy: Haga's standing and efficacy in the Porte was seriously compromised by his intemperate personal life and his flaunting of communal cultural mores regarding appropriate moral behavior between foreign men and Ottoman women. The challenge for historians in developing a clearer understanding of the nexus of sex and diplomacy is to ferret out these stories from the archives: because of their sensitive nature and the potential professional and personal ramifications for the men involved, they only rarely make an appearance in the documentary record, leaving us only the occasional, tantalizing hint into the intimate side of early modern diplomacy.