This chapter considers naval officers’ experiences of loneliness at sea and in colonial space through a comparative analysis of the journals of Lieutenant Ralph Clark and ship surgeon Dr Joseph Arnold. Covering the period between the French Revolutionary and Napoleonic Wars, it suggests than men’s differing emotional communities, especially the domestic realm and homosocial public culture, impacted their experiences, or lack thereof, of loneliness. Investigating their experiences of emotional connection through the lens of class and race, it argues that the formation of emotional communities amongst the officer class in the British navy served as a boundary differentiating themselves from lower class convicts and colonised peoples, especially the Eora and other First Nations in and around the early colony in Warrane (called Sydney).