The Vulnerability of Asking Questions

How asking questions builds intimacy—and thoughts on an ending

I want to begin honestly: Over the last few weeks, I’ve contemplated shutting down Boss Barista. I’ve felt like I’ve lost focus on why it is I’m here, coupled with the fact that being so online has felt increasingly distressing over time. I’m sure everyone has experienced the absolute dread of seeing, as Bo Burnham so eloquently put in his 2021 special “Bo Burnham: Inside,” “a little bit of everything all of the time” (from his song, “Welcome To The Internet”):

But as I was transcribing my latest episode with Renata Henderson and Bartholomew Jones of Cxffeeblack, I listened back to an anecdote that Renata had shared about when Bartholomew proposed to her, and something shifted:

Renata: I was teaching at a school, he came up—there's so much more context to this—but we were in an auditorium and he started freestyling about questions. This idea that questions show the vulnerable side of you. And when you ask a question, you're really placing yourself in the position to be truly seen by this person because you’re saying things that you may or may not know. And I like, I don’t know, something that was deep and I was like, “Ooh, okay.”

So he goes in this long thing and then he gets something out of his backpack and jumps down to where I was in the audience. I’m the only person there. This was during parent-teacher conferences, might I add. So I don’t know if there were parents in my room, but he jumps down and gets down on both knees and says, “Will you marry me?”

I’m always stoked to re-air former podcast interviews; it gives me the chance to provide transcriptions for episodes that don’t yet have them, or which existed before I started this newsletter. I first shared this episode in July 2020 and re-aired it earlier this week, and I’m glad I did—there’s so much in this conversation that’s valuable and worthwhile, and I’m glad new subscribers and listeners get a chance to sit with it. And I think I needed to hear Renata’s story again, too.

The idea of vulnerability, and the way we ask questions of each other—the meta conversational threads that you’ll notice in many Boss Barista interviews—come up once again in the episode. At one point, the three of us talk about how people open up coffee shops without really questioning why. “Does this business need to be here?” “What’s my intention by opening up in this neighborhood?” “What do I hope to achieve by opening a service-oriented business?” And while I don’t want to dismiss the big lessons we touch upon here, on my latest listen, it was the intimacy of Renata’s story that reminded me why I like to write, and why I like to interview people: I like asking questions.

This also made me think back to a book I almost included in my recent Boss Barista reading list, but which I ultimately left out (I thought it would be kind of cheesy, and difficult to explain). But you may remember that one viral Modern Love piece; it came out in 2015 and was called “To Fall In Love With Anyone, Do This.” Every week or so, the New York Times publishes personal stories about all facets of love, and this piece, authored by Mandy Len Catron (who I believe—I remember hearing this, but I can’t verify it anywhere—is an ex-coffee employee, which affirms my secret, yet-to-be-publicized thesis that coffee folks are equipped to do everything), introduces 36 questions that can supposedly help anyone fall in love.

The questions themselves, which range in intimacy from, “Would you like to be famous? In what way?” (no, I wouldn’t, although my position on this has changed dramatically over the last few years—if I could publish stories under a pseudonym, I would) to, “Of all the people in your family, whose death would you find most disturbing? Why?” (my estranged father’s, because his space in my life is so mythic, so unreal, that I’d have trouble rectifying the finality of our estrangement). I like these questions because they’re meant to develop intimacy, and show that intimacy is a practice rather than something you just fall into.

After first reading Catron’s piece in 2015 (and later reading her book, called “How To Fall In Love With Anyone: A Memoir in Essays”), I asked pretty much everyone I wanted to know better if they’d answer these questions with me. By that point, I’d been writing for a few years, and I think this practice distilled for me what I actually like about writing: Learning more, listening closely, and hopefully cultivating a new connection. I like that asking questions allows you to admit curiosity, and show care for someone else. Questions allow you to be vulnerable.

I’ve noticed that I’m always effusive when publishing new podcast interviews, and maybe that sounds a little hollow after a while, but I really mean it. I’ve come to realize that’s because these interviews allow space for intimacy to form. I typically leave feeling so moved by my guests that I truly mean it when I say I love every interview.

We could relate this all back to the service industry, and acknowledge that truly successful coffee shops, restaurants, and bars ask questions of their community, and admit when they don’t know what’s best, when change is needed. But it’s more than that. I think almost every moment of crisis within the service industry—and coffee specifically—can be traced back to needing to ask more questions. (To return to my secret belief that baristas can do pretty much everything—you’ll hear more about this in a future episode—baristas, and other service folks, are trained to ask questions, to be curious and open to peoples’ needs.)

Over the last few weeks, I’ve had to really assess why I keep podcasting, why I keep writing. Boss Barista will be six years old in February, and I often wonder how a project or a publication like this one ceases—if there will be a clear sign that it’s time to end, if it will quietly fizzle out, or if I’ll simply delete everything and pretend none of this happened. But anytime I really consider those options, I’m reminded of the hundreds of moments of intimacy and connection I’ve gotten to be part of, and that’s enough for right now. Even if this doesn’t go on forever, I plan to keep asking questions. That, I hope, will last forever.