This study intends to explore the philosophy of “fate” as contended by Zhuangzi, which, if comprehended simply literally, may unavoidably give an impression that Zhuangzi consents to the notions of commonsense fatalism or destiny, but if it were explored further and not confined to the superficial meaning, it would not be difficult to come by the following implication: (Ⅰ) Unlike commonsense distinction between blessing and misfortune, life and death, predicament and freedom, and so on, Zhuangzi has actually based his philosophy on a wisdom of non-opposability in which opposites are inextricably confused and opposition transcendental; he states that all life encounters such as blessing/misfortune, predicament/freedom, etc. are constant flux reciprocally flowing to each other; which in turn shapes each other and becomes one with each other, while further indicting the synthetic nature of fate that is not be sundered; in other words, Zhuangzi has turned around the commonsense by pointing to the oneness nature of fate, which has surpassed the concept of oppositional dichotomy, bearing a meaning that is non-oppositional, which corresponds to the meaning of the “Way” or “dao”. (Ⅱ) Zhuangzi sees comfort with fete not because of having no choice but reluctantly accepting the predetermined fate, but because knowing fate being a constant flux by nature, bearing no distinction, opposition or sunderance, which is an understanding that any life encounter reserves in it the flux and the transience, and thus can be viewed as the whole, and that whatever life encounter is, there is no departure form the whole, and thus can leave no regret or loss, making it possible to accept fate in a placid and life-comforting manner, and making any life encounter bearable and born unconditionally. (Ⅲ) Although Zhuangzi advises to “accept it as fate for having no alternative” and “pursue what fate has brought by nature, but not what is has not”, the utterance should not be comprehended merely by its literal meaning, nor should it be falsely perceived as the lamenting over life encounters; it rather points to the oneness and non-oppositional nature of fate behind all life encounters which is transcendental to all opposable concepts, and earthlings should select or sunder any part of the whole with the conscious of individuals.