The Apostolic Penitentiary was the most important medieval papal office, which distributed different kinds of «grace» in the name of the pontiff: absolution, dispensation, license, and special declarations. The powers of the Penitentiary allowed the office to deal with marital issues among other things. Christians from all over Christendom could turn to its authority to ask for dispensations or absolutions allowing them to be married or to remain in their already contracted marriage despite the existence of a marital impediment. This article offers glimpses of what the Penitentiary material can offer for scholars interested in medieval marriages through a detailed analysis of c. 4,200 petitions directed to the Penitentiary during the pontificate of Pius II (1458-1464). The article answers to following questions: Who turned to the Penitentiary? Where did the petitioners originate from? What were their needs?