This study focuses on the construction of an amorous relationship in Chaucer’s poetry. It is observed that threats are recurring speech acts in Chaucer’s wooing scenes. Such threats are conditional and coercive in nature, having a bearing on the role and exercise of free will. A speech act definition of a threat is offered in the article. The definition is based on John Searle’s analytic model and threats in wooing scenes are treated as commissives, given their conditional nature. Such threats are also often playful in varying degrees. Drawing on a number of examples from Chaucer’s major poems, the article examines the nature of playfulness and the question of how it is grounded in the content and the context of a threat. The issue of a lady’s consent is framed in the article by the larger background of the partly conflicting Germanic and Roman cultural traditions both impacting Chaucerian England.