Coulda, woulda, shoulda… In Overthink’s long-awaited epsiode 82, David and Ellie fret over the meaning of regret, in everything from life-altering career decisions to sloppy teenage breakups. They consider the usefulness of regret — if it has one at all — and explore its relation to a life well lived, investigating its philosophical lineage from Confucius and Aristotle to today. Can 20-year-olds regret? Can dogs? Is regret ever rational? And, when does remorse turn into existential despair?

Works Discussed

Aristotle, Nichomachean Ethics
John Danaher, “The Wisdom of Regret and the Fallacy of Regret Minimization”
Shai Davidai and Thomas Giolvich, “The Ideal Road Not Taken”
Michael Ing, The Vulnerability of Integrity in Early Confucian Thought
Paddy McQueen, “When Should We Regret?”
Michel de Montaigne, “On Repentance”
Carolyn Price, “The Many Flavors of Regret”
Justin White, “Revelatory Regret and the Standpoint of the Agent”
Russian Doll (2019)
Sliding Doors (1998)
Magnolia (1999)

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