The mother–child relationship is essential in the development of a healthy child, who can grow up trusting his/her own perceptions and understanding of the social environment. Teenagers naturally experience a period of transition in search of their own identity as individuals, thus being really exposed and vulnerable to being recruited by jihadists. In this particular stage of development, the teenager tries to free himself/herself from the tutorship of the family and looks to experience something new outside the family frame. One of the defining characteristics of this stage is a tendency to take things to an extreme and to see things in black and white, while emotions are experienced as very intense, overwhelming and sometimes difficult to control. Teenagers are easy to impress, convince and manipulate, especially by their social milieu outside the family of origin. In the cases when the relationship with the family of origin becomes tensed – whether the child has been neglected or spoiled during childhood, or when there are tensions between parents or the family is conflicting – the teenager looks for validation outside the family environment. Any opportunity to do something out of the ordinary and apparently easy to accomplish might seem attractive for this category of individuals, especially for those that do not enjoy family support. The illusion of becoming famous or the attraction of glamour might seem desirable at this age. This is one of the main reasons why Jihad has had such a significant impact on Western converts to Islam. Therefore, the aim of this study is to provide an analysis of the case of Boicea Luigi Constantin (Umar al Rumaani), a Romanian that adhered to the extremist ideology of the Islamic State, who does not come from a Muslim family, yet underwent a fast self-radicalization process. In order to better understand Boicea’s case, we will try to present the result of the investigation conducted on the family environment, his interests manifested at an early age, and the tragic events that contributed to his radicalization; in other words, we will try to present the general context in which self-radicalization occurred.