This chapter analyses the journals of two young men seeking to establish themselves in their professions in the first half of the 19th century. Required to travel and live away from their familial homes, the changes they encountered left them feeling disoriented, dislocated and distanced. These circumstances produced a range of emotions and states that were akin to the modern concept of loneliness but were, nonetheless, historically specific to the social, cultural and gender structures of the period. For both men, it was distance—physical, conceptual and emotional—that was the frame through which they experienced and conceived of the ‘emotions cluster’ that speaks to us of loneliness. A further aspect of the men’s experiences that can be historicised is how they managed and disciplined these states through standards of masculinity.