How to Talk with Strangers

It comes down to mindset

A seminary professor once told our class to meet one new person every day. Why? Because the habit grows your conversational skills, awareness of people, and compassion and empathy. Those are important aspects of being a pastor. I also believe human connections are vital and loving one's neighbor means talking with strangers. Meaningful conversations emerge from the soil of small talk. Lastly, people are fascinating. But it does take work to have meaningful conversations, especially with those whom you've just met. As someone told me recently, everyone is a museum but we hang out in the lobby. 

I began practicing my professor's advice over ten years ago. Over the past decade (excluding two COVID years), I've averaged meeting five new people a week. How does one do that when people’s eyes are glued to their screens and their ears are stuffed with earbuds? Let's start with the minor stuff and move to the major.

First, set a measurable goal. It's helpful to have a target. You can start with one new person per week. Or set a goal of starting conversations with people you see regularly but haven't talked to. These could be neighbors, coworkers, clerks, etc. Next, consider what meeting a person means. I define it as a minimum 5-minute conversation where you learn the other person's name. It's somewhat arbitrary because you can have a meaningful conversation without learning someone's name and vice versa. But I do think learning someone's name is a good way to start a relationship and open the door for future interaction.

Second, start a tracking mechanism. I take notes on most people I meet, especially after the first conversation. Note-taking helps me to remember the person's name and other relevant details such as hometown, occupation, demeanor, and my first impression of them. I take notes after I meet with people in my church because I forget important things like what to pray for such as upcoming trips, conversations, surgeries, company lay-offs, etc. If I'm on my game, I set up calendar reminders to pray and check in.

Third, develop conversational skills. I have a repertoire of questions I ask people but I typically rely on questions and statements related to context such as something that just happened, the surroundings, the weather, the other person’s clothing, etc. It doesn't matter how you start the conversation, it just matters that you do. Some people dismiss small talk as shallow and meaningless. It's not. It shows that you're safe and people can relax around you. But the most valuable conversational skills are your nonverbal cues, especially during the first 5-10 seconds of an interaction. Tone, posture, hand gestures, and facial expression matter far more than the actual words you say. You can open "Hi, I'm an axe murderer" with a smile, strong eye contact, good posture, and open hands and people will respond far more positively than if you mumble "Hello, how are you?" with your shoulders slumped, arms crossed, and looking away.  

Being upfront about one’s agenda and making specific statements helps invite further conversation. For example, I invited church neighbors to our Super Bowl Party. I introduced myself and stated my intentions in the first 10 seconds. If they balked at the invite but seemed open to further conversation, I asked if they were rooting for the 49ers. If they said yes, I replied with a grin, “So you’re OK rooting against Taylor Swift?” It was an easy entry point for people to discuss their feelings about the pop sensation. The only way to get better at these skills is to practice in real life. Set the bar low for yourself, get out there, and start talking.

Fourth, frequent social spaces. I regularly put myself in situations where it's easy to meet someone new. This might be the toughest step, especially if you don't have a pattern of going out. My easiest but most limited context is Sunday church service. On average, I meet one new person at church every Sunday. This is a very predictable context for me and easy to start a conversation. Unfortunately, newcomers tend to be most guarded in this situation as they know I'm a pastor so it's rare to get past the lobby. I accept that limitation and that's why I seek other contexts.

I play pick-up basketball regularly at 24 Hour Fitness in Sunnyvale. Nobody cares that I'm a pastor and it's a great context to meet people but it does take greater intentionality. It's too easy to focus on playing and shallow small talk. Every context has its limitations. I've only gotten past the lobby a couple of times but when it happens, it can get quite deep because sports bond people like few activities outside of war and work.

I'm also a regular at my friend's cafe. I lead a community building project called Coffee and Questions. Our church pays for a person's coffee if they're willing to pick a question out of a jar and discuss it with me and a friend. I've met dozens of people this way and had many meaningful conversations. The hardest moment is the first five seconds when someone decides whether they'll talk to you. The second toughest moment is picking a closure point and exiting the conversation gracefully. Transitions are hard and where social skills are honed and refined. One thing that's also important is I've learned to relax but also be ready. I do sermon preparation and email at the cafe and I focus on what I'm doing but I'm also prepared when I notice someone to start a conversation.

For parents, your children's school and activities are fantastic venues to meet people, especially when you're waiting around to pick up your kid. Put down your phone and see if you can get another person to put down theirs. 

Fifth, adopt an optimist/pessimist mindset. First, I assume people are lonely and want to talk about themselves. I also assume people don't want to take the first step to make conversation because we are scared of rejection and initiative requires effort. I imagine I am performing a service by going first. I also think I'm an interesting person and I think people are interesting. I work at being genuinely curious about other people. I'm not sure there's a better reason to talk with strangers. I always expect to learn something new and I'm rarely disappointed.

At the same time, I also prepare for the reality that people don't want to talk with me. And it has nothing to do with me. Why? I have many moments when I'm in a rush, getting work done, or feeling down. When I'm in that state, I don't want to talk to anyone. It's nothing personal. When someone doesn't want to talk with me, I imagine the other person having similar reasons as I might.

Lastly, I accept awkwardness. Awkward moments are inevitable, especially at the beginning of an interaction. Think of it as waking up early on a cold morning to work out. It takes effort to get out of a warm bed. It's not smooth or organic. If talking with strangers were easy and natural, everyone would initiate conversations and meaningful connections would pop off in the night sky like a meteor shower.

I worked on this post at 24 Hour Fitness and met R. I asked about her jump rope as I noticed she was doing double-unders and kipping pull-ups, uniquely CrossFit movements. As a former CrossFitter, I know the first rule of CrossFit is you must talk about CrossFit. She was also one of the few gym goers not wearing earbuds. We had a friendly conversation about the training app she uses and bemoaned the death of CrossFit during the COVID. She appeared grateful I started the interaction. 

As you develop your mindset and skills, you'll find your assumptions about people challenged and discover a richness to the human experience that cannot be captured by any screen. I hope you'll find increasing delight in this scenic byway of conversing with strangers.