In the last decade, there has been an increase in scientific, forensic, and social interest around the issue of stalking. Several studies have focused on the behavior of the stalker and the dynamics implemented, identifying a problem related to "rumination" or repeated sequences of obsessive ideas and thoughts with related impulsive and compulsive behavior. Unfortunately, an impaired reflective function (RF) associated with ruminative distortion is relatively underinvestigated in its possible link to stalking conduct. The aims of the present research are: (a) to investigate whether dissociative tendencies are present in our sample when they stalked the victim; (b) to assess the quality of their RF in relation to their early attachment and their crime narrations; and (c) to describe the quality of the stalkers' mental process. We administered a structured questionnaire, the Dissociative Experiences Scale-II (DES-II), and two interviews, the Adult Attachment Interview (AAI) and the Index Offence Interview (IOI), to a sample of 14 male stalkers detained in two northwest Italian correctional facilities. The interviews were then evaluated using the Reflective Functioning Scale (RFS), a measure of the subject's ability to infer mental states in self and others and analyzed through the Interpretative Phenomenological Analyses (IPA). The DES-II average score (M = 12.03; SD = 8.98) did not differ from the mean of the general population found in scientific literature, whereas AAI and IOI RFS scores ranged, respectively, from 1 to 3 and −1 to 3. Stalkers in our sample showed a significantly lower RF score in the narratives related to the crime (M = 1.1; SD = 1.66), compared to the RF of the AAI (M = 2.4; SD = 0.65). From the AAI and the IOI emerged a difficulty in connecting mental status and behaviors and a ruminative thinking, with a recurrent sense of injustice, a distorted mental process and a little or no awareness of their own and others' mental states. The rehabilitation of mentalizing capacity should be considered as a priority among these subjects, to further strengthen a reflective attitude and to make them more responsible for their own behavior. Clinical implications and intervention procedures were discussed.