This article examines the phenomenon of prolonged singlehood in Israeli orthodox society on the basis of interviews and two scenes from plays performed by two orthodox theaters during 2006-07. These plays reflect the vibrant discourse taking place within orthodox circles on this pressing issue, and the article contributes to understanding of the orthodox singles' problematic status in a pro-family society by combining analysis of the theatrical presentations and information gathered through qualitative research methods: interviews, field journal entries, and observations. The inter-disciplinary approach adopted here incorporates the fields of gender studies, anthropology, literature, and performance studies. It allowed me to bridge the gap between the personal experiences I learned about in the interviews and the theater produced by the singles. Prolonged singlehood is presented in the plays as a religious trial for unmarried adults, and their future release from their problematic status is in God's hands. This ostensible solution and explanation of the phenomenon enables singles to invalidate the communities' criticism of them and to subvert their own self-criticism.