Two wildly different stories from last weekend, and what they might teach us about dialogue:

The introverts’ lunch. I just spent four days in Chicago at Live It Out, the 2014 conference of the Gay Christian Network. The structure of this conference was unusual: the occasional plenary session or workshop block surrounded by large swaths of time to connect with others in the LGBTQIA community.

Something about this format played right into my limitations. My inner introvert simply couldn’t figure out how to flow with the informality of it all. I felt lost and awkward and unsure how to proceed.

Thank God for the whiteboards. Anyone could pick up a magic marker and scrawl out a message, invitation, tip, or what have you on these boards. Many established groups had posted their get-togethers.

Inspired (quite literally, I believe), I posted the suggestion of an introverts’ lunch.

Apparently it caught the eye of other introverts: when lunchtime came, and I arrived at the designated meeting place, four people were waiting. We had a wonderful time at the Rockit Bar & Grill. (Travel tip: if you like butternut squash soup, you must try Rockit’s.) Contrary to stereotypes of introversion, the conversation never flagged. And somehow, from that lunch, I gathered whatever it took to flow with the rest of the conference.

Shoeshine Ken. There’s something about Chicago’s street people that I’ve missed in other major cities: rather than beg, a number of them sell. One (may or may not have been a street person, but he approached me on the street) sold me his demo hip-hop CD. Another asked me to buy postcards to fund a mission.

And then, walking down Michigan Avenue, I heard this gravelly voice remarking on my boots and how I should clean them. Before I knew it, Shoeshine Ken had squirted some lotion on my footwear and was telling me, alternately, about his life and the need for good shoe care.

I know, I know. You’re “supposed to” ignore these folks. But if I had, I would have missed one of the richest experiences of my weekend. For about 20 minutes, Ken and I talked about the geography of being homeless in Chicago. I heard about Lower Wacker (under which many people sleep at night), social services for homeless people, the value of a good heating grate in subzero weather, and how Ken plies his trade where many wealthy people and their shine-eligible shoes pass by.

So here’s what these stories are teaching me to do:

  • Talk with anyone. Everyone. The famous conference speaker has something to teach us, to be sure. But so does the hesitant introvert, the young person wrestling with gender identity, the homeless entrepreneur. Yes, there can be safety issues, and one should keep oneself safe. But if you can manage it, don’t let the opportunity pass by.
  • Find a way that works for you. In many situations, it’s not just about screwing up courage to talk with people or join a group lunch or what have you. More often it’s about creating structures, like the introverts’ lunch, where dialogue can take root. These structures can be practical, like strategies, or they can be internal, like the transformation of our hearts toward curiosity and compassion.

That second point teaches me something else too: something broader. Dialogue is difficult. Life is difficult. Sometimes, like many homeless people, we can do very little on our own to improve our situations. But sometimes—as with me and my introverts’ lunch, or Ken and his shoeshine business, or adversaries in a delicate dialogue—we can do something. And that something can occasionally make a big impact.

It’s the beauty of our species: our innate ability to do things—things that foster not only dialogue, but the fruitfulness of our lives.