This presentation explores the challenges of working with patients who struggle with relationship ambivalence through a clinical case discussion. Patients caught between the needs for connection and independence often carry early developmental disruptions, such as impairments in whole-object relations and object constancy—milestones critical for healthy individuation. An object relations framework helps identify these gaps and address them through the therapeutic relationship. A here-and-now approach invites the therapist to attune to enactments, ruptures, and regressions—often rooted in fears of abandonment or intrusion—and to explore them collaboratively. By containing and processing projected affects, the therapist fosters the patient’s capacity for reflection, self-soothing, and sustaining stable object relations. Finally, the presentation will highlight how termination often stirs fears of abandonment and offers a crucial opportunity for patients to experience endings as healthy goodbyes rather than as rejection