Hans Christian Andersen's The Naughty Boy (1835) isn't your typical fairy tale, it's Cupid gone mischievous. We unpack this strange little story published alongside Thumbelina, trace Cupid's origins from Greek Eros to Victorian matchmaker in a diaper, and explore how Andersen may have written his own struggles with love right into the tale. Along the way, we have some laughs, discuss Andersen's continuous self-inserts, and dig into why Cupid’s arrows might sting more than they charm.