Connecting with Strangers

Monday night I was in Waterloo, Ontario, in the basement flat of Rachel Brnjas (who is on staff with the Tamarack Institute, which organization I was in town to connect with) eating homemade pizza and enjoying three hours of conversation about community with strangers. 

One of the most interesting moments occurred in the final hour, when the gathered mutlitude reflected on their experiences with trying to make meaningful (as opposed to merely pleasant) contact with people they were meeting for the first, and perhaps only, time—as in on a bus or train, or at a large social event.

This captured my attention because I realized I had a somewhat complicated response, based on my having lived almost four decades in intentional community, where social expectations are often significantly different than in the mainstream context.

One of the most precious aspects about intentional community is that it supports and promotes more intentional engagement, by which I mean connections that are more heartfelt, stimulating, resilient, and authentic (interactions that are less trivial, freighted with bullshit, interlarded with posturing, and/or impeded by armoring).

To be sure, all relationships in community are not precious, just more of them—to the point where community veterans often find it easier to connect at depth with other community people they've never met before than with family and lifelong friends who have never pierced the veil of community living experience.

So there I was Monday evening discussing with strangers the art of meaningful connection with strangers. It was a self-referential conversation. While I sat there it occurred to me that my response was heavily influenced by my community experience, and that I had only a vague sense of how much that might have been shared by others in the room—which, of course, is invariably the situation when engaging with strangers—you never know at the outset what the context of social engagement is for them.

The conversational stew was made even more savory by the exotic quality of the group's composition. With the exception of Will (a community silverback who had spent 18 years with Jubilee Partners in Comer GA) and me, there didn't appear to be anyone else north of 30 in attendance, and that vast majority of the dozen or so folks present had deep roots in the Mennonite Church, all as social activists, and some as evangelical Christians. 

This was definitely not a social configuration I find myself in very often, which made it all the more intriguing. It had been a number of years since I was last in a room (outside of church) where Jesus was regularly inserted into the conversation as an illumination rather than as an expletive.

As Monday night pizza with Rachel is an open invitation, there was an informal flow to both the conversation and attendance all evening. Some were there the whole time; others came and went. Some never spoke; some were hampered by English not being their native language or culture; and some jumped in early and often. While a few were inspired to suggest community-related subtopics from time to time, and there were occasional attempts to facilitate openings for the less assertive, mostly the conversation flowed organically.

On the question of how best to engage strangers, there was wide agreement that you were unlikely to achieve depth without being willing to go first, and that there was delicacy in how best to make the initial overture.

Here are the elements of my reflected response to this excellent question, and the sequence in which I suggest they be attempted:

—Testing for openness to engagement
This can be trickier than merely asking the person near you if they'd like to converse. While that might work, it typically works better if you're sensitive to eye contact (or its absence) or body language. Does the person appear to be available?

The fact that you're interested in connection (even eager for it) does not imply any certainty (or obligation) on the other person's part to be interested in your offer. They may not be open to engagement of any kind. Or they might be open selectively, which is the interesting case.

Some of this is context. People at a party, for instance, are less likely to be picky than the person sitting next to you on the train. That said, you may be the wrong gender or age to interest the other person—there are all manner of nuances to a stranger's limited availability. 

Sometimes you can be persuasive by being bold; sometimes by being charming; sometimes by being innocuous (which is different than vacuous); sometimes by being clever; sometimes by being funny; sometimes by asking a question. That said, I think what tends to work best is an opening gambit that invites the person to say something about themselves—something with possibilities for more than a one or two-word answer.

While there is nuance about going too far too fast (I dis-recommend starting with an inquiry about whether anyone in their family has ever been institutionalized for mental illness), through careful observation it is often possible to pick up subtle clues on what the other might be to willing to share. If they look confused about where to put their luggage on the train, you might ask if this is their first time on Amtrak. If they look overwhelmed while milling at a reception, you might start with a question about whether they know anyone in the room. I'm suggesting that you aim for modest engagement on a relative safe topic that shows you're paying attention.

—Offering something revealing and genuine
Assuming you get a green light to your opening (or at least not a red one), I suggest looking for a way to say something about yourself that takes the conversation to a graduated deeper level, where you are sharing unilaterally about something close to your heart. Rather than prodding them to be vulnerable with a probing question, demonstrate your willingness to go there yourself first. 

While you might get turned down (perhaps it doesn't feel safe enough; perhaps they're not that interested in you; perhaps they're not connecting with what you shared), at least you're operating in the right territory. If it isn't going to get more meaningful, how valuable was the connection anyway? (If you're going to get turned down, you may as well make it be for your truth; rather than because of the off color of your joke, or because you failed to stick the landing of your clever comment.)

Caution: Note that I advise a graduated deepening. You want to take the escalator down, that invites depth; not the high speed elevator that demands it. While there's considerable variety about what others consider safe, keep in mind that we're talking about strangers. Blind guessing about what people you don't know will consider acceptable depth (vulnerability roulette) may be exhilarating, but it's not generally a good strategy if the goal is meaningful engagement.

—Listening for the way in
Once you succeed in getting people to open up at all—even on a modest level—you're in a great position to gently guide the conversation into increasing depths. All you have to do is pay attention. It's been my experience that people will invariably tell you what matters to them if you simply listen.

Most people like talking about what matters to them (instead what doesn't). If you're flexible about where you find depth and the path by which you get there, there should be abundant clues about what will work.

As a professional facilitator, my nightmare is not having people jumping up and down and screaming (in those situations you never have to guess where people are at; it's obvious); it's people with stony faces who aren't talking at all. Silence is the hardest thing to interpret accurately, since it can mean so many things and there are so few cues with which to work. 

Maybe they're exhausted and falling asleep. Maybe they're bored and zoning out. Maybe they didn't hear what was said. Maybe they're afraid to offer a differing opinion. Maybe they're afraid of sounding stupid. Maybe they're locked up in reaction. Maybe they're confused. Maybe they haven't missed anything but simply have nothing to add. Silence can be almost anything.

Once you've successfully established a conversational flow, look for the topics that hold meaning for the other person. Rather than looking the openings that you can use as a springboard for sharing your insights about life, look for the openings where they can share theirs.

• • •

In writing this essay, I'm not suggesting that the "right" thing to do is to engage strangers at every opportunity. Rather, I'm trying to offer some thoughts about how best to do so productively, when you're open to stranger things happening.