I really enjoyed The Jottery: Thought Experiments for Everyday Philosophers and Part-Time Geniuses by Andy Selsberg. Each page has a question or mental challenge — think of it as something between a really high-end fortune cookie, a profound zen koan, and a really great late-night dorm room discussion. Next time you’re going to be in the car for more than half an hour with a friend or family member, bring this book instead of listening to music or letting the kids watch a movie.

In ten words or fewer, explain why it’s useful or stupid to ask people to explain things in ten words or fewer.

List a handful of elevator tension-breakers, and a handful of elevator tension-makers.

A service specializes in planning vacations that seem unremarkable at the time, but that people look back on with an almost unbearable fondness and longing. Suggest a few itineraries.

List at least ten groups about which you could grandly announce, “These are my people!”

Selsberg’s books (Dear Old Love: Anonymous Notes to Former Crushes, Sweethearts, Husbands, Wives, & Ones That Got Away, You Are Good at Things: A Checklist) have been featured by The New Yorker, NPR, The Chicago Tribune, The Guardian, and Penthouse, and he has also written for GQ, The Believer, Oxford American, and Salon.