The theme of loneliness has not yet attracted much interest from economic historians, whereas solitude—more specifically, singleness and widowhood—is a theme that has already been explored by historians interested in the role of women in modern European economics. Based on a series of letters sent in 1778 by a travelling salesman to a Lyonnaise modiste (Mlle Mandier), his patron, during his six-month journey to Italy, this chapter focuses on the different levels of loneliness that affected the two protagonists. Using gender as an analytical tool shows that the issues and constraints due to loneliness were quite different for these two protagonists, if only in terms of their self-image, and allows us to challenge certain suppositions about the expression of emotions.