The study’s main objective is to identify and analyze the attitude toward prayer of teenagers in a denominational school in Romania and the need to use AI-assisted tools. To find a satisfactory answer, we considered it necessary to identify how they pray, i.e., freely or by calling on the prayer book, and whether they questioned whether artificial intelligence could be an agreeable support. The research also takes into account the documents of the Romanian Orthodox Church from which the attitude of the Hierarchy towards new technologies in general and artificial intelligence in particular emerges. How attentive is the Church to these realities, and how open is it to incorporate them? Does it have any good reason to consider tools like e-rosary in the Catholic world or Alexa Pray in the Anglican world in the near future? The introduction addresses Romania’s socio-political, educational, and theological context, and the discussion focuses on how the literature on digital religion and its subchapters is received in the Romanian theological landscape. The research method includes qualitative, questionnaire, and textual analysis; it is an interdisciplinary approach, namely practical theology and the study of digital religions. The questionnaire was administered to 216 respondents, respecting all research ethics requirements. The results reveal that young people prefer to pray freely, use the prayer book moderately, and have not gathered information regarding artificial intelligence that could help them. However, they are open to a future offers from the Romanian Orthodox Church, including AI-assisted tools.