Should neighborhoods change? Is wearing a suit a good way to quit smoking? Why do people think that if you do one thing, you're against something else? Is monogamy a trick? Why isn't making the city more fun for you and your friends a super-noble political goal? Why does a computer last only three years? How often should you see your parents? How should we behave at parties? Is marriage getting easier? What can spam tell us about the world?

Misha Glouberman's friend and collaborator, Sheila Heti, wanted her next book to be a compilation of everything Misha knew. Together, they made...