Filling in for T.J. McCormack, Walter Sterling explores the intersection of romantic expectations, financial burdens, and human curiosity during a Valentine's Day special. The program transitions from a pragmatic discussion on the rising costs of holiday gifts and the perceived "traps" of dating etiquette to a deeper investigation into modern conspiracy theories. Sterling posits that the human drive to create complex narratives—ranging from alien abductions and UFO sightings to the mysterious Epstein files—is a unique hallmark of a successful, advanced society with the luxury of intellectual leisure.

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