This chapter examines the diarist Hermann von Weinsberg’s descriptions of everyday conversations, which are incredibly revealing of the notions of privacy within his social circles. Weinsberg recorded these conversations in his diary, a record meant to be kept secret from his contemporaries but at the same time intended to be read by his future family members. The chapter explores the creative textual approaches (writing about some conversations at a later time, trying to hide them entirely, subtle hints, referring to other texts, switching to Latin, etc.) that the diarist used while trying to balance between these two aims in his records. Péter’s contribution highlights different spaces in which private conversations could take place, and how people could negotiate what they understood to be the boundaries of privacy while communicating with people.