Davy Rothbart's book, How Did You End Up Here?: The Surprising Ways Our Questions Connect Us is a short manual for making small talk bigger. Rothbart is the editor of FOUND Magazine, which publishes "found stuff: love letters, birthday cards, kids’ homework, to-do lists, ticket stubs, poetry on napkins, doodles– anything that gives a glimpse into someone else’s life." It's not surprising that he's a curious person, someone who wants to learn more about the people he meets. On a recent press tour for the magazine, he asked audiences, "What question would you most like to ask a stranger?" And then he started asking people those questions. The book is a collection of questions that hopefully move past small talk into real conversation. The idea is that people want to connect, and if you're brave and curious and ask people questions about their lives, they will answer.
A life long introvert with a life long aversion to small talk, I am curious but not brave when it comes to striking up conversation with strangers or even people I know casually. I would like to change that. It's a common misconception about us introverts that we don't like people or that we can get along just fine without social connections. We can't; we're just not good at making those connections, and we can get away with being crap at it because we don't need very many. Rothbart's strategy for connecting by asking questions seems solid to me. The people I know who are really good with people are the ones who know how and what to ask to get others comfortable and talking.
I'm going to start small by asking some of Rothbart's questions on Facebook and answering some of them here. If you'd like to join the conversation, you can jump in on the comments or, better yet, volunteer to answer a question in a guest post.