The cultural, political, and geographical liminality of Wallachia (modern day Romania) between West and East generated a double interreligious conversion of its rulers in the age of the state formation. This straddling between Eastern and Western civilizations transformed Wallachia, at least in the Middle Ages, into a preeminent liminal space. Within relatively short periods of time, the Wallachian rulers were regarded as either fervent Western Catholics, eager to convert to the Western faith, or as devout Eastern Orthodox, as faithful Christians or as schismatics. Had they been converted to one of the confessions? Was there a hybrid double religious belonging to both faiths? This study explores the nature of the ties between religious conversion and political allegiance. Drawing on contemporary theoretical debate and historical case studies, it argues that a “double conversion” of the Wallachian rulers can be reconstructed in the space between Eastern and Western religious and political realities.