This essay argues that although Oscar Wilde, like many poststructuralist thinkers, observed that objectivity remained impossible, his sense of humor led him to different conclusions: serio ludere or serious play, a tradition extending from the Renaissance at least through Philip Roth, defines Wilde's philosophy, not a system, but rather a series of thoughts and behaviors going to the root of the word. His love of wisdom drove him to sacrifice anything to learn something new. His planless plan—or plan not to plan—remained "live by whim," and reveals his aversion to the three Rs, namely, reason, rationality, and realism.