It is only in recent times that historians of emotion have capitalised on the early modern sermon as a key primary source, acknowledging its function not only to instruct, but to move a congregation. However, the affective aspect of early modern sermons has yet to be investigated in conjunction with the personal and emotional lives of the clergy who delivered them. This chapter utilises Protestant preachers’ interpretations of Genesis 2:18 (“It is not good that the man should be alone”) as a springboard to ask the following questions: how were their theological readings applied to their own lives, if at all? In the absence of the term “loneliness,” how did these divines express feelings of emotional isolation? Examining sermons, treatises, personal documents, and monumental inscriptions, this study reveals the multifaceted attitudes of the clergy towards marriage and loneliness which were reflected in their lives and writings, both public and private.