In this lecture I wish to focus on children who considered conversion from Judaism to Christianity in late medieval German lands. A number of judicial cases preserved in Hebrew manuscripts as well as in archival documents shed light on the wide implications conversion had on family structures: When one parent was baptized and the other chose to stay loyal to their former religion, relationships and family ties were unravelled and the offspring of converts often found themselves caught between religious and social worlds. In these documents it is attested that Children of converts from late medieval Germany stood before a spectrum of options on the threshold of baptism, and were not forced comprehensively into the dominant religion.This research will address the following questions: What were the decisive factors influencing children in their decision? What role did Jewish and Christian authorities play in this scenario? How did gender compliment the treatment regarding such children? Can we speak of a revised meaning to the legal term "free will"? I will further suggest examining a connection between baptism and rites of passage concerning adolescence in both religions at the turn of the medieval era.