This essay focuses on the challenges adolescents face as they progress in the process of object removal. The loosening of primary libidinal object ties triggers object loss and a unique form of loneliness specific to adolescence, which may be misdiagnosed as depression. Rather than stemming from a fear of loss of love from the primary object, the loneliness results from the adolescent's need to transfer love from primary objects to new adult relationships not yet available to him. The resultant emptiness may be defended against by overuse of the Internet, alcohol, cigarettes, drugs, and food. These defenses are manic in quality in that they suggest an orally based regressive attempt to “take in” and “expel out,” preserving the felt “lost” object and converting the loneliness into elation. Clinical vignettes illustrate work with adolescents wherein the ability to tolerate lonely feelings is recognized as a developmental accomplishment leading to personality growth and maturity.