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100 icebreakers for talks with strangers: A Q&A with TED Book author Davy Rothbart

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If you could ask a stranger any question, what would it be? This is the question Davy Rothbart set out to answer when he embarked on a nationwide tour to celebrate the 10th anniversary of his magazine, Found. Rothbart — a writer, reporter and documentary filmmaker known for his curiosity about other people’s lives — traveled across North America, trying to discover what people most wanted to know about each other. At every Found event, he would hand out slips of paper to the audience that asked some variation of the question: “If you could ask a stranger any question, what would it be?” The answers he got back were surprising, hilarious, sad, strange and heartfelt. Most interestingly, patterns started to emerge; people with drastically different backgrounds were curious about similar issues.

That’s when Rothbart realized he had collected a treasure trove — that he could gather these questions together to create a guidebook for people who want to get to know those around them. His new TED Book, How Did You End Up Here?: The Surprising Ways Our Questions Connect Us, is a collection of more than 100 of Rothbart’s all-time favorite questions. It also includes essays on connection and curiosity, stories from the road and strategies for getting people you don’t know (yet) to open up.

Eager to try out asking a stranger some questions, we decided to start with Rothbart himself:

What inspired you to collect questions from people around the country?

I’ve been collecting personal notes and letters for the past 10 years and publishing them in Found; each find gives us a glimpse into other people’s lives in an incredibly raw and intimate way. But why wait for these revealing tumbleweeds to cross our path? The opportunity to connect with someone new is always hovering close by. On last fall’s 79-city tour to celebrate Found‘s 10th anniversary, I asked members of the audience in each city to generate questions they’d want to ask a stranger. Then I invited a volunteer from the crowd onstage and put these questions to them. Their answers were always deeply meaningful.

What do you think we gain from posing questions to people we don’t know?

We’re surrounded by strangers all the time — on the bus, on the elevator, walking down the street. I think it’s natural to be curious what other people’s experience of being human is like. When we ask odd and surprising questions to people we don’t know, we come to learn how similar our hopes and dreams are to the people around us. Sharing our own stories with another person and getting a chance to hear theirs — it’s a transaction which leaves both sides feeling far richer.

With all the technological tools we have for communicating, is our culture past this sort of real time, face-to-face engagement? Why is it still necessary?

Facebook, Twitter, email and texts offer us a way to be constantly engaged with a wide social network, but how much can really be communicated in 140 characters? Personally, I love these tools, but they must be balanced with connecting “IRL” — in real life. In Real Life, our connections are deeper, more meaningful and more enduring. Questions about someone’s life, asked with genuine curiosity, interest and empathy, are generally answered with deep openness. It’s hard to replicate this kind of exchange through text messages.

Are we particularly disconnected from each other at this point in history?

I do think that the rise in cell phone use has coincided with a diminishing rate of genial exchange between strangers. When we can be texting, emailing, movie-watching and game-playing wherever we are, we have less downtime in our travels through the world and fewer opportunities to engage with the people around us. I’m no soapbox preacher — I get devoured by my smartphone myself. But I miss those moments waiting in line at the supermarket, on an airplane before takeoff, or sitting at the counter at a diner that used to be spent chatting with the folks around me. Now there’s a social contract that states that these times are to be spent checking our phones, not interacting with strangers, and something has been lost there.

Some of the questions in this book are particularly challenging. What do you find is the hardest type of question to ask a stranger?

I think the first question is always the toughest. Simply beginning a conversation with a stranger can feel like a difficult thing to do. That’s why I like to start off with the most innocuous kinds of questions — What’s your name? How was your day? What did you do today? — and then move on and mine more deeply.

I’ve found that questions about challenging topics — death, grief, sex, money — are generally received with great warmth when asked with genuine curiosity. People are very willing — even eager and relieved — to speak about things they don’t often get the chance to.

How do you imagine people using this book?

My hope is that people will use this book in any number of ways — as an icebreaker with people they’ve just met at a conference (hint: at TED2013, TEDActive, or a local TEDxLive screening next week), an orientation, at high school or college; with the person sitting next to them on a plane or a Greyhound bus; with a beloved grandparent or aunt or uncle or cousin; with friends and acquaintances on a road trip; with a prospective boyfriend or girlfriend on a second or third date; with themselves, to spur personal writing and reflection.

I’ve already seen these questions work to bring people closer together and connect more deeply, and I’m excited to get these questions into other folks’ hands so they can also see how real the rewards can be once we take a chance and engage with the people around us.

How Did You End Up Here? is part of the TED Books series. It is available for the Kindle and Nook, as well as through the iBookstore. Or download the TED Books app for your iPad or iPhone.