When Does an Affair Begin?

Or why people cheat.

Jul 25, 2026

∙ Paid

A quick update before we begin- I’m in the final stages of editing The Stoic Manual: Meditations on the Art of Living, a collection of 150 Stoic meditations on living well. It’ll be released soon and included free for all Annual and Lifetime members.

Welcome! The Stoics were deeply concerned with how we live with other people. Relationships are one of the hardest places to practice love, good judgement, kindness, patience, duty, and self-discipline. That’s why last time we talked about Why You Will Marry the Wrong Person. Today’s essay looks at adultery as how we evolve to receive the person in front of us, how we handle resentment, how we honor the roles we’ve committed to, and how ordinary evenings either protect love or prepare its ruin.