Therapeutic attachment can help a college-aged woman deal with separation from her mother, making the transition from dependence to mutually supportive peer relationships. An insecure relationship experience with the mother replays in treatment as a patient resists therapeutic influence. Serving as a secure base, a therapist can help a young woman let go of potentially self-fulfilling negative expectations and develop trust that she can find responsive caregiving, internalizing a capacity to love and be loved. Using two case examples that illustrate different attachment styles, one anxious and the other avoidant, I explore my struggle to deal with the injury of feeling discounted while seeking opportunities for connection. Examining our interaction, I consider the patient's and my own role in perpetuating patterns of insecure attachment. By helping a young woman to better understand her mother as a separate person and to express autonomy within the treatment relationship, therapists can foster healthier attachments while supporting individuation.