Since moving to a new state, I’ve been meeting a lot of new people. This experience has been as enlightening as it’s been challenging, as I’m not often extroverted enough to put myself out there. Thankfully, many of the lovely people I’ve met have made this exceptionally easy by asking a lot of really thoughtful questions, showing true interest in getting to know me, and helping fuel the discussion with their open hearts.

I've realized over time that some people just have that gift: they’re able to engage anyone they meet in a real conversation. I believe that’s a true talent. Many of us fumble for the right words or try too hard or can’t be ourselves right away. So whenever I’ve encountered people who make it easier to relax and really talk to me, I try to take note. What’s their method? What is at the root of their inquisitiveness? And then I turn these questions back to myself: what do I really want to learn about this person sitting across from me? How can I walk away from this moment feeling like I know them better?

The first thing I try to do is eliminate the obvious. As Elizabeth Gilbert recently said, “Nothing kills a conversation faster than ‘Where are you from?” or ‘What do you do?’” Why? Well, consider your own answers: are they most defining pieces of your identity? Are they even that interesting? Gilbert assessed that maybe the person standing in front of you isn’t that proud of their current profession, a possibility I completely understand. For a three-year window of my life I had a job that I never wanted to talk about, and yet every time I met a new person, that was the first thing they wanted to know about me. As for location, that doesn’t often have much to do with the person you actually are. Sure, there are regional traditions and landmarks, but being from New Jersey is more an uncontrollable fact than it is a distinctly personal thing about me (unless of course you count the times I’ve answered that question and have had people say some version of “I knew it!”).

"Joy in the universe, and keen curiosity about it all - that has been my religion." - John Burroughs

So what should we ask instead? I don’t think we have to memorize a script or rehearse in the bathroom mirror. What I’ve started doing, and what I’ve learned from observing others, is considering, what I would I want to be asked? What would I want to talk about with someone? What would I want to share about myself, my fears, my hopes, what excites me, what I’m going through? With this in mind, it’s a lot easier to form questions (and answers) that come from a place of honesty. It’s so easy to behave how we should when we meet someone new. I’m not saying it makes more sense to open up too quickly or showcase all your emotions and inner workings at once. But our truest connections come when we’re being ourselves, when we’re embracing our humanity as what we have in common. And humanity isn’t always pretty or professional or enviable, but it is real. It’s making space for empathy. And in creating a place for empathy to exist, we create a place for each other to belong.

So here are some examples of questions I’ve asked (and been asked) in the last six months:

What are you most excited about in your life right now? Elizabeth Gilbert gets credit for this one, too. During a recent talk in Denver, she shared how she asked this question around the world during her Big Magic book tour. She shared a handful of the responses she received, some of them beautiful, some of the heartbreaking, all of them well worth the riskiness entailed in this ask.

What were you like in college? Hoo, boy. Looking back on yourselves together can be a big part of fueling connection. Sometimes this can be one that doesn’t paint a very flattering picture of ourselves. Underneath the late nights and the (likely) bad decisions, you were a person learning to navigate yourself. It’s a vulnerable time. How are you different from who you were then? How are you exactly the same?

How are you handling that? This one typically comes after someone shares a big moment they’re facing, good or bad. How we handle adversity or big change is often something we can’t predict, even about ourselves. Talking through something can be a big part of how we work things out or come up with new solutions to our problems.

What’s something you used to think was true that you don’t believe anymore? I love this one. It creates such a good opportunity to reflect on how much you’ve grown and changed. It can be as simple as something you misconceived as a kid. Whatever the answer is, funny or revealing, it usually sparks something deeper about who we are now and how far we've come.

What are you reading lately? This one is for the library nerd in me, but I'm always interested in what pages other people have been turning. You might find you truly connect on a subject or a character or a series. Or you might learn to open up to something you'd previously dismissed. If nothing else, you might walk away with a good book recommendation that you might not have discovered on your own.

If you could have anyone's singing voice and anyone's dance moves, who would you choose? This one made me laugh. And there's a good chance the answers you get will make you laugh, too. (Mine, in the moment: Amy Winehouse and Freddy Mercury, of course.)

What questions have you been asking lately? What answers have you been giving? Think a little more (and a little deeper) the next time you talk to someone, whether they're a new acquaintance or an old friend. Let your curiosity lead you.


Helen Williams is a Colorado transplant who is passionate about cooking, writing and combining the two on her vegetarian and vegan food blog, green girl eats. She strives, every day, to be less sorry. When she's not in the kitchen, you can find her reading, loving the community at Holstee or trying to pet your dog.

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