This chapter will focus on the overlap and benefits of a humorous and philosophical attitude toward the world and our place in it. The first part of this chapter’s title borrows from Kierkegaard and before him the Christian apologist Turtullian, who once quipped about the central contradictory tenets of Christianity, in putatively ironic fashion, “I believe because it is absurd.” The idea that we laugh at absurdity, contradictions, or an incongruity between the way we thought the world was and how we now recognize it actually is, goes back at least to Arthur Schopenhauer. Very often when we discover a mistake in reasoning, a fallacy, we laugh. This is interesting. Contradiction, inconsistency, irrationality, absurdity, nonsense, ridiculousness, repugnance, fallacy, etc., are some terms philosophers have used to refer to instances of poor reasoning. They are also concepts useful in analyzing why laughter often accompanies fault-finding endeavors. The historian of philosophy Will Durant tells us that genuine philosophy begins when one learns to doubt; we can say something similar with humor-trust me.