How freely could men and women in the late medieval period shape their emotional and sexual lives? Centered on the diocese of Catania within a comparative framework, this book examines how betrothal and illicit relationships were regulated in Sicily between the fourteenth and sixteenth centuries. By illuminating the intersections of affection, sexual conduct, and mechanisms of ecclesiastical and secular control, Fabrizio Titone contributes substantively to the ongoing historiographical debates surrounding marriage formation and social discipline in the medieval era. In its pages, we find personal plans, frustrated and accomplished, fears and complaints, and strategies of discipline and rejection. The analysis, based on a wide range of primary sources, sheds light on an unknown world, made up of individual stories and reflecting social dynamics that extended far beyond the individual couple. The Church, Marriage and Sex in Late Medieval Sicily challenges the conventional narrative of systematic female subordination while tracing the steady constriction of freedoms once protected by canon law. By showing that the Council of Trent merely gave legal form to earlier developments, the book offers a fresh account of marriage, sexuality, and governance in the region.