From my hard chair at the kitchen table, I can see the fluorescent green numbers on the oven clock climbing up. At 8 p.m., I cave to jovial peer pressure and agree to play one more round. At 10:15, we’ve forgotten the cards spread out in front of us. At 11:30 we laugh at ourselves, make predictions that we will “pay for this in the morning,” and don’t leave. Midnight pads through the kitchen, cat-like and unnoticed. At 2:30 a.m. we shuffle and stretch and bundle up to scrape the frost off our windshields and drive home.
I feel the giddy magic that always comes with a snowy night and the spontaneous intimacy of sharing the wee hours of the morning with others. Times like these are rare and precious. I don’t know how to trigger them. I turn the conversation over in my mind like a hard candy. What made tonight different? The people were the same church regulars. But pleasantries exchanged after church or Bible study always seem to fall flat.
For one thing, the conversation around the kitchen table was real. It was not all serious or grave. Honesty and joy are not mutually exclusive. That night, we laughed so hard, my eye makeup was smudged to dark rims around my eyes. Embrace the grace of the ridiculous.
The shortcut past the small talk I’ve discovered—and used to screen all sorts of budding relationships from potential friends and dating app matches—is a good old hypothetical question. The weirder the better. Here are my top five friend-making hypotheticals:
1. If you could go back and redo a year of your life or add twenty years to your life, which would you choose? At first glance, this is an unobtrusive question. But, at its heart, it’s about regrets and the comparative worth and wisdom of youth and old age.
2. Assume you have a time machine that can only go backwards. What is the farthest back you could go in time and survive if you got stuck and had to live out the rest of your life there? The object here is not to find out how good your friends actually are at sailing viking long ships or living in a world without paper towels, it’s to find out how good your friends think they are.
3. Through a series of bizarre magical events, half of your body is going to be transformed into an animal—centaur-like. But the chaotic forces at work are not completely vindictive. You can choose what animal…and what half. What do you choose? You may think this is about favorite animals, and you would be incorrect. This question is about problem-solving in physical space. It’s how you find friends with the spatial reasoning skills to set up a tent in the dark and pack a car for a road trip.
4. If you could give one gift to every person in the world, what would it be? (“Beauty pageant answers” like “world peace” are frowned upon.) Ultimately, this question is about values. What, according to you, are the world’s biggest needs? What spurs you to compassion?
5. If your local library offered a new service where a device, shockingly like a USB cable, could be plugged into your left ear and download a character trait or virtue into your personality, no work required, what would you want to download? Simply, this is about who you want to be.
6. Bonus (not a hypothetical, but a good question): In what subject area, no matter how specific, would you consider yourself an expert? The more ordinary the answer the better. Examples of good answers, in my opinion, include home town tour guide, boxed mac and cheese preparation, and encyclopedic knowledge of the history of Lego.
The common theme in these questions is a simple invitation to imagination. That’s how we made friends in school, after all. We invited other kids to play. At what age does that sweet, hospitable gesture become ineffective? I say “hospitable” because in asking silly or fantastical questions, you make space for another person to be a larger, truer version of themselves.
“How are you?” is part of a bland, obligatory call and response. There is little freedom to depart from the script. “What do you do?” is similarly bound by a rigid expectation that your profession is the most interesting or important thing about you. Is that really our most pressing inquiry when confronted with another human invested with the imago dei?
When we ask better, more creative questions, we are metaphorically scooching over the chairs and getting down an extra place setting. We are fluffing up the pillows on the couch and unfurling blankets. It’s an invitation to “come, stretch out your wild ideas and your hare-brained hopes.”
One nice thing about being a grown up: we can stay up past our bedtime to talk.

Emily Stroble is a writer of bits and pieces and is distractedly pursuing lots of novel ideas and nonfiction projects as inspiration strikes. As an editorial assistant at Zondervan, she helps put the pieces of children’s books and Bibles together. A lover of the ridiculous, inexplicable, and wondrous as well as stories of all kinds, Emily enjoys getting lost in museums, movies old and new, making art, the mountains of Colorado, and the unsalted oceans near Grand Rapids. Her movie reviews also appear in the Mixed Media section of The Banner and her strange little stories of the fantastic are on the Calvin alumni fiction blog Presticogitation. Her big dream is to dig her hands deep into the soil of making children’s books as an editor…and to finally finish her children’s novel.

As someone who hates (but understands the place/need for) “small talk”, I’m always seeking new ways of creating space to know others and be known.
I loved your thoughts and the intentionality behind what might seem like simple questions.
What I often find sad, however, is that for many people, they do not recognize such questions as invitations for deeper connection and often, missed relationships are the result.