This article examines the emotional landscape of courtship and engagements in seventeenth-century Sweden. By using a framework by Illouz, understanding courtship as a cultural technique aimed at creating certainty in socially risky situations, the courtship of two women by one student is examined. The analysis moves from the intimate interactions of the couple to the family, the community and lastly the ecclesiastical and university authorities. The article shows that the main sources of uncertainty in the courtship process stemmed from procedural and ontological uncertainty—the order of courtship, the rituals of engagements and the significance of exchanged gifts were not clear, causing confusion and disruption in the courtship process.