The aim of this study was to test the association between Stalking-Related Behavior (SRB), urami and communication skills. As variables related to SRB, three factors were investigated: the frequency of SRB, the persistency of SRB and the variation of types of SRB exhibited. As a variable of motivation for SRB, urami was investigated. As variables of communication skills, six factors were investigated: expressivity, assertiveness, decipherer ability, other acceptance, self-control, and regulation of interpersonal relationships. A web-survey was conducted using 191 male and 197 female participants who have been rejected by someone they have loved (hereby referred to as “the target”) within the last five years. The results of a multiple-group analysis revealed a model that was common in both men and women which showed that poor self-control and other acceptance increased urami in the experience of rejection, and urami increased both the frequency and variation of types of SRB exhibited. Furthermore, the results found that as the level of assertiveness decreased, persistency of SRB increased. Finally, the limitations of this study and future prospects about the research of stalking in Japan was discussed.