Eighteen U.S.-based doctoral students in counseling or clinical psychology were interviewed by phone regarding experiences of crying in therapy. Specifically, they described crying as therapists with their clients, as clients with their therapists, and experiences when their therapists cried in the participants’ therapy. Data were analyzed using consensual qualitative research. When crying with their clients, therapists expressed concern about the appropriateness/impact of crying, cried only briefly and because they felt an empathic connection with their clients, thought that the crying strengthened the relationship, discussed the event with their supervisor, and wished they had discussed the event more fully with clients. Crying as clients was triggered by discussing distressing personal events, was accompanied by a mixture of emotions regarding the tears, consisted of substantial crying to express pain or sadness, and led to multiple benefits (enhanced therapy relationship, deeper therapy, and insight). When their therapists cried, the crying was brief, was triggered by discussions of termination, arose from therapists’ empathic connection with participants, and strengthened the therapy relationship. Implications for research, training, and practice are presented.