What do you say in four minutes?

A decade ago, the New York Times published a Modern Love essay on how to fall in love with anyone. Reeling from a breakup and wanting more control over her love life, writer Mandy Len Catron turned to science: she discovered a 20-year-old psych study in which a researcher facilitated two strangers falling in love by asking each other a series of 36 questions. One night, Catron recreated the experiment in a bar with a date—and it worked. They, too, found love, and her essay became one of the Times’ most read of 2015.

It’s easy to see the headline “To Fall in Love With Anyone, Do This” as clickbait now, but not at the time. I remember thinking, there’s a recipe? Intention and desire to fall in love are essential too, and Catron says as much. Still, great questions do lead to intimacy and closeness. They can help us re-author who we are, which is why they’re a staple of coaching.

I use a questionnaire when I begin a relationship with a new client, and people often tell me it’s one of their favorite parts of the experience. I’m always on the lookout for new insightful questions, which is one reason why I revisited the love experiment. I was intrigued by number 11 on the list: “Take four minutes and tell your partner your life story in as much detail as possible.”

I asked a friend if we could test the storytelling question because I wanted to understand it from the inside out.

We met at a downtown bar, ordered drinks, and figured out how to keep track of time. Obviously, we aren’t strangers, so the experiment was more like what we might include or leave out in our stories, unrehearsed. Both of us shared where we were born. We spoke of our hometown, and the influence of art and culture in our lives. He spoke more of his career, while I talked about relationships. Both of us also included stories of loss. During my friend’s turn, I watched him transform from a man into a little boy as he talked about his childhood best friend, who died of leukemia in middle school.

I’ve always loved the exploration of the self through questions. In the 1990s, I discovered the Proust Questionnaire in the back of Vanity Fair, and it became one of my favorite magazine features, along with Harper’s Index. The Proust Questionnaire is a set of personal questions named after French novelist Marcel Proust. Originally a Victorian parlor game, Vanity Fair transformed it into an interview template for celebrities, with questions like “what is your idea of perfect happiness” and “what is the trait you most deplore in yourself.” The 90s were a golden age of magazines, and I read as many glossy, scented pages as I could. Many of them had quizzes that were silly and fun, but flattened personality into types. Only the Proust Questionnaire revealed people to be witty, weird, and soulful at once.

Great questions can be surprisingly insightful. They don’t only build connection—they also make us, save us, evolve us. We’re always casting and recasting stories of the self. A few days after our bar experiment, I texted my friend to see what struck him in my story … if I felt tenderness for the kid he was, did he have a similar experience? What did he hear?

“A youth, and even a lifetime, of not making waves,” he responded. “Fitting in. Going along as a survival tactic.”

It landed, and quietly broke my heart because I try so hard to project the opposite. In my four minutes, I shared how I liken myself to Wild Bill Hickok. The metaphor came to me years ago while watching Deadwood. I related to Hickok’s persona—principled, charismatic, loyal, world-weary. He was an excellent shot. He believed in fairness, even when law was absent, and he often served as a catalyst of change, even if he didn’t benefit from it. I’ve made sacrifices too, personally and professionally. I often think of others first, and sometimes I can’t help it. Choices like this feel more heroic and purposeful, less tragic, when I liken myself to a gunslinger for justice.

But my friend picked up on another thread. I also told the story of being a “good girl” who takes up as little space as possible, minimizes her voice, and performs out of a sense of duty. Who would that be in Deadwood—Martha, the schoolteacher who marries the sheriff out of obligation, or Alma, the widow managing her husband’s gold claim. I can feel my chest constrict thinking of their lives, trapped in expectation and dust in the Black Hills of South Dakota. Meanwhile, Hickok roamed free. In the end, both stories are true. I’m wild and tame. I obey and break the rules.

Great questions invite complexity like this to emerge, whether they’re asked with the intention to fall in love, or build connection, or discover the self. Great questions let us consider how we’re powerful and powerless, and how we live with this, with sand we can’t shake from our shoes. Great questions give us the structure to untangle the story of the self in relationship. They make space for our more fragile, childlike, and tender parts to evolve, and they help us claim the agency that is ours. Great questions let us name what’s unfolding in real time, even in only four minutes.

If this resonates, you might like to work with me one-on-one. Let’s connect.