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Plato's Lessons on Letting Go of Unhealthy Relationships

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12.11.2025

History often provides perfect metaphors for our personal struggles. Few historical episodes offer more relationship wisdom than Plato's three ill-fated journeys to Sicily in the 4th century BCE. While these events might seem distant and academic, they contain profound insights about a challenge many face: trying to change someone who isn't ready to change.

First Visit (387 BCE): Plato visited Dionysius I, the tyrant of Syracuse. His philosophical views on justice and temperance offended the ruler, ending the visit poorly. The only positive outcome: Dionysius's brother-in-law, Dion, became inspired by Plato's teachings.

Second Visit (367 BCE): When Dionysius I's son took power, Dion convinced Plato to return and educate the young tyrant, hoping he might become the "philosopher-king" Plato described in his writings. Dionysius II showed initial interest but balked when confronted with the discipline philosophical study requires. Raised in luxury and accustomed to flattery, he wasn't willing to do the difficult inner work that genuine transformation demands.

Third Visit (361 BCE): Despite clear evidence of failure, Plato returned after Dionysius II promised he was now ready to embrace philosophy. In his Letter 7, Plato reflects on this journey, making clear that the failure wasn't his own teaching but rather that Dionysius II had lost whatever small

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