Psychology had an early start at the University of Copenhagen in the first half of the 19th century, where it was taught as the major part of a compulsory course required of all first-year students. Particularly important in the establishment of psychology at the university was Frederik Christian Sibbern, who was professor of philosophy from 1813 to 1870. Sibbern wrote numerous works on psychology throughout his career. In his first book on psychology, Sibbern expressed the view that the ideal psychologist should also be a poet. Søren Kierkegaard, Sibbern’s student, was precisely such a poet–psychologist. Kierkegaard discussed psychology in many of his works, reflecting the gathering momentum of psychology in 19th-century Copenhagen, Denmark. The article brings out some aspects of Kierkegaard’s poetic and literary-imaginative approach to psychology. In his opinion, psychology was primarily a playful subject and limited in the questions about human nature it could answer, especially when it came up against the “eternal” in man’s nature. Kierkegaard had a positive view of psychology, which contrasts sharply with his negative views on the rise of statistics and the natural sciences. In the latter half of the 19th century, psychology turned positivistic at the University of Copenhagen. This left little room for Kierkegaard’s kind of poetic psychology.