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From the moment adolescents walk into my office, I wonder how long they will stay. Many adolescents just stop coming without warning, while others leave voice mail messages: “Hey Doc, it's me. Sorry I can't make it. See you.” This is especially true for many of today's overly programmed, fast-paced teens who are accustomed to communicating by cell phones and instant-messaging. Competition from social and after-school activities including sports, SAT classes, tutors, and religious education leaves little room for psychotherapy. Given adolescents' proneness for acting upon feelings, lack of self-reflection and resistance to delay gratification, the adolescent therapist has only a small window of opportunity in which to engage them in treatment. Adolescent treatment presents numerous challenges, not the least of which is how to make a genuine connection with teens so they will want to stick around long enough to accomplish the emotional work before they take leave. This article addresses the various developmental aspects of adolescent termination and how this process parallels the psychological struggle to leave childhood and the family of origin behind. Psychological separation in adolescence consists of a complex set of internal transformations involving one's relationship with self and others and, while often intertwined with, is distinct from physical separation. Clinical case material will be presented to illustrate the internal and external battles these adolescents exhibit around termination from psychotherapy. It concludes with recommendations for addressing the length of treatment and termination issues early in the treatment.