Philosphical counseling is a philosophy in practice, meant to offer practical directions about life and help people look at the world from a more positive standpoint through assisting people to help themselves in a philosophical way, obtain the best strategy of their own, and enter a balanced and peaceful state of mind. Philosophical counseling can be applied in different fields and work as guides to real life in terms of marriage counseling, issues of life and death, career counseling, development of self-respect, issues of self-identity, religious and spiritual questions, issues about life and being, and interpersonal relationships. This paper focuses on applying the methodology of philosophical counseling to Zhuang Zi's philosophy and exploring his methods of philosophical counseling. Based on the First Seven Chapters of Zhuang Zi, we show how the master of humor in Chinese philosophy helped people with his allegorical philosophy. In the complicated world with various problems, what the Zhugan Zi's suggestions for us to examine our own lives and look at life from a free and easy perspective? Though living in the dark world of harms and complicated interests, we could still realized an ideal way of life with a new attitude toward the world. Zhuang Zi's wisdom and insight help people look at life from a different perspective, improve the quality of living, and lead meaningful lives; besides, the free and easy philosophical disposition makes the body and the soul sustain in harmony and dynamic balance. Zhuang Zi's humorous thought helps people break away with their habitual thinking and open their minds, that is, restore the balance and turn our life into a new direction when anything is out of joint, whereby the quality of life can be improved and the free and easy state of mind can be reached.