Newly Orthodox Jews, or ba'alei teshuvah, represent a significant demographic phenomenon in most American Jewish communities and thus have been the subject of a modest number of sociologically-driven studies. Consequently, psychological considerations of the ba'al teshuvah experience have been either minimized or completely neglected, and therefore this study attempted to fill this gap in the literature by qualitatively examining some transformational aspects of religious change in male ba'alei teshuvah by interviewing two sets of participants: male ba'alei teshuvah (n=6) and professional outreach rabbis (n=5). Both the rabbinic and ba'al teshuvah participants in this study represented prominent cultural Orthodox subgroups that engage in intra-religious outreach (Modern Orthodox, Yeshivish, and Chabad-Lubavitch). Three common pathways towards increased religious observance were identified and explored: the intellectual, experiential, and interpersonal, with specific emphasis placed on issues uniquely affecting male returnees. Different impediments related to social integration within established Orthodox communities were also covered, as well as challenges regarding the progressive observance of certain religious rituals and strictures. In addition, addressed for the first time was the issue of mental-illness among some ba'alei teshuvah and the attracting qualities of Orthodox Judaism for this population. Finally, a novel approach to the conceptualization of healthy religious conversion was offered from a deocentric object relations perspective. Drawing heavily from the theoretical advancements made by Moshe Halevi Spero (1992) as well as Christopher Bollas (1987b), this explanatory framework was designed assuming the existence of a real God object as well as certain psycho-spiritual endowments that, in conjunction with “existential traumas,” provide the psychic space necessary for individuals to approach self authenticity.