The current study is based on the notion of an empathic dialectic, marked by states of emotional resonance and regulation, which has been described by contemporary theories of therapeutic empathy and empirically supported by research on non-therapists. We operationalized emotional resonance as personal distress empathy, and we sought to examine how activities promoting self-regulation impact the association between personal distress empathy, and other facets of poor self-regulation. This was accomplished through an online study, which administered several self-report instruments to a sample of 158 non-therapists and 139 therapists of various levels of experience, collecting participants’ demographic information, attachment status, level of shame-proneness, the fear of invalidity, and personal distress empathy. We examined the impact of several moderators on the paths from attachment anxiety, shame-proneness, and the fear of invalidity to personal distress empathy; and, thus, on the indirect effect between attachment anxiety and personal distress empathy. For our first hypothesis, we expected therapist status to significantly moderate the paths in this proposed meditation. For our second hypothesis, we anticipated personal therapy sessions would significantly moderate this meditation. For our third hypothesis, we expected that both personal therapy and therapist experience level would moderate this mediation. Most notably, our results indicated that the fear of invalidity explained the association between attachment anxiety and personal distress empathy, and this mediation was stronger among non-therapists when compared to therapists. Yet, personal therapy did not similarly impact the relationships among these variables. Implications for future research are discussed.