This article explores the relationship between loneliness and psychosis, with respect to how psychosis constitutes a longing for connection and reality, how harrowing loneliness both precedes and follows psychosis, even triggering it in some individuals. It also examines some strategies individuals with psychosis use to cope with loneliness and how psychosis and its treatment further isolate a person, increasing loneliness. Finally, it discusses how therapists who treat psychosis experience a particular kind of loneliness in the countertransference. Case material is presented.