Some will talk to you because they feel confused or threatened or insulted by your show of friendliness… Others will talk to you because they are friendly souls, happy to respond to the human overtures that come their way. Try to keep these conversations going as long as you can. It doesn’t matter what you talk about. The important thing is to give of yourself and see to it that some form of genuine contact is made.”

– Paul Auster, Gotham Handbook

This is the passage I was reading a month ago when I first heard about The Daily Muse’s 30-Day Challenge. At the time, I was comfortable. I had been living in San Francisco for a little over a year and had fallen into a routine of traveling to and from work, attending events on weekends, making my way here and there in a nice little haze of music and self-reflection. Moving to the city had been a big change for me, and I had finally acclimated to my new environment.

But I wanted more.

So I decided to take Auster’s advice (even though it was meant for New Yorkers and not San Franciscans) and talk to strangers—to become an active participant in the life around me instead of a passive observer. And though his passage is lovely and inspiring and left me dreaming about having all kinds of adventures and deep conversations with strangers that looked suspiciously like Walt Whitman and had all the answers to life, I didn’t. My real-life experiences with strangers weren’t nearly as romantic. They were however, educational. Here are a few things I learned:

1. Nobody is a Morning Person

Nobody. Not one single person I talked to in the morning was especially engaged or excited about it. Sure, I met some nice people, but my AM conversations were endured, not enjoyed. I think there is a sort of unspoken (key word here) agreement between morning commuters that the trains should be as quiet and as annoyance-free as possible, so we can all have a chance to wake up. It’s like we aren’t even people yet on the morning train; we’re just half-awake, sleepy ghost people. We aren’t fully-formed human beings until 9:30 AM.

2. Much Human Interaction is Awkward and Uncomfortable

I hate to say it, but it’s true. And that’s the main hurdle I had to get over during this month. If I wanted to reach out and meet someone new or have a new experience, it was going to get a little weird. Because people are weird. We’re hard to figure out. We’re different, and when you get different people together, they are going to say and do things that don’t quite fit with one another.

3. Baseball Brings a City Together

I’d say about 50% of my conversations this month have been about the San Francisco Giants, the playoffs, and then the World Series. Even if someone was obviously not a big sports fan—or didn’t even know what game it was in the series—we could still chat like we were all part of something together. I can’t quite put my finger on it, but there’s something about baseball, about being in this city at this time, that feels important. Like we are a part of history, even if it’s just the small history of this game and this team. It seems silly—maybe we should be more concerned about the election, the economy, and what’s happening in the world—but there are so many complicated issues that separate us, it’s nice to have something simple that can bring us together.

After last week’s struggles to force conversation, I decided to take it easy on the last week of my challenge. Instead of trying to get people to talk to me, I tried to find people who wanted to talk. And you know what, they’re out there.

After watching a Giants game at a bar near my office, I noticed a man sitting alone. I asked if he was excited about the win, and then the conversation went on from there. Turns out, he owned the restaurant next door and stopped in to watch the game. We chatted about how he decided to start his restaurant, how people thought he was crazy, and how maybe he was. But it wasn’t an easy conversation. We’d talk and then there would be a pause. We’d both sit there sipping our beers staring straight ahead, trying to think of something else to say. Maybe I’d turn back to my friends for a bit. But when he left, we turned to say goodbye.

“It was nice to meet you,” he said.

And it was.

I had to travel for business this week, and as I made my way through airports and hotels, everyone seemed willing to talk. I met a group of teachers attending a conference, a woman who had two kids and never got to read except on planes, another woman who packed three suitcases for a three-day trip, a college finance professor who was a huge Chicago Cubs fan, and then an older man who was my absolute favorite person I met this entire month. (I liked him even better than the Week One woman who told me to never be sorry.)

He sat next to me on my flight home. I was in the middle, he had the aisle, and his wife sat across the aisle so they could talk. They were delightful. There’s something about the way older couples attend to each other while traveling that’s so sweet to me. He helped with her bag, she grabbed him a pillow, he asked how her book was, and she asked if he’d finished his puzzles. For the most part the man was quiet, but then toward the end of the flight he asked me if I was a student because I was reading a book and taking notes about it. I said no, and explained that I just like to write about what I’m reading so I remember it.

“I don’t remember anything anymore,” he said.

Then I pointed out that he had been completing puzzles for three hours so he must remember a few things. He laughed. He showed me how to do three different puzzles. He explained how he was better at harder puzzles than easier ones because he took more time on them. He wasn’t from San Francisco but he’d lived there for more than 50 years. He was retired and proud of it. He and his wife had been visiting Kentucky and Indiana, where they’d spent days driving around to see all of their grandchildren. He didn’t like to drive and he didn’t like flying. He thought our plane was going to fall into the ocean.

“We weren’t meant to fly,” he said. “We are going to die soon; I’m sure of it.”

But we didn’t, of course. We made it back to the ground and said our goodbyes. I laughed with the couple about how we didn’t tumble to our doom, and as we walked through the gates together, I thought, “Huh, so this is what people who are happy look like.”

If I had donned my headphones the entire flight, I never would have met them. And it’s not as if they changed my life—I’m sure I’ll forget all about them a year from now—but they did make my day. It’s a small thing, I know, but it’s a great thing, too.

In his advice, Auster said: “I’m not asking you to reinvent the world. I just want you to pay attention to it, to think about the things around you more than you think about yourself. At least while you’re outside, walking down the street on your way from here to there.”

That’s the main thing I’ll take away from this challenge, that feeling of being more aware of others. No, I’m not going to chat up every stranger I meet from now on or force conversation on people in elevators or on the street. (I am so happy this challenge is over and I don’t have to do that anymore!)

But I will take my headphones off more often. I’ll continue to look for that person alone at a restaurant, the buzzed group of friends laughing with each other on the train ride home, the tourists who are lost and need a little direction, or the old woman who smiles to herself while she waits for her morning coffee. I will try to talk to these people. I will try to learn their stories and tell them my own.

And you can, too.

Next time you’re at a bar or on the train, take a look around. There’s probably someone standing there, looking around the room as well. Someone alone sitting next to an empty stool. Or someone with her headphones off trying to make eye contact. (Yes, that person has been me many, many times this week.)

It’s a small, silly thing, I know. But I realized that I’m a small, silly person. And talking to people I don’t know is just one more way I can make my little world grow a little bigger.

Updated 6/19/2020