In the past few weeks, both the New York Times and Washington Post have run much heralded pieces with poor headline size choices on the value of talking to, and sometimes even with, strangers. I’m not often this far ahead of the curve, but my trilogy on this topic—Chatting Into the Unknown, Vols. I and II, and Kiwi Convo—launched almost three years ago. And while even a cursory search reveals both journo-giants flitted onto the topic once or twice in the past, each of my essays offers a decidedly more entertaining and convincing case than either the old gray lady or the new rich chrome dome. (Malcolm Gladwell did write a 2019 book on the subject, but he’s an arrogant ass and so does not merit consideration in anything.)
Still, I’m not one to rest on my laurels, and not only because for a long time I didn’t know what that meant, which was actually better because then you find out and as usual it’s just so dumb. And as I have long said, I never back down from a challenge, unless I haven’t Wordled or my shoes are still wet. So I started thinking about how to take this endeavor to the next level, and an idea came to me that I got down before I got distracted, which almost never happens any more so color my ass grateful.
It’s even rarer I get an opportunity to quote myself in a way that seems any less than totally self-aggrandizing, to wit, I argued then and do now for the increased urgency to become a better stranger engager as follows: “These days I think talking to strangers is sliding from a lovely option into the realm of social necessity, as while I certainly hope some unification meteorite will strike the earth and instantly end racism, sexism, toxic capitalism and the rest of the globe’s top 20 ills, until that happens we may have to heal the planet one carbon-based life form at a time.”
I, and now the two leading newspapers in what will someday be known as the Era of You Call That Journalism?, have explained to readers fully why and even mostly how they should talk to strangers. But today’s reader demands solid, real-world value even in culture candy clickbait such as this, so I decided to do a primer on, as precisely as possible, what to say to strangers in the kinds of places and situations they tend to hang out. You’re all busy people, and even if you sincerely want to share a moment with a random fellow two-legged hairless air-breather just for the sake of connection, who has time to prepare cheat sheets for stuff like that? And it’s a scientific fact that no one is spontaneously witty and charming more than 35% of the time.
Confidence is a great thing to carry into worthwhile but unfamiliar and perhaps even unsettling endeavors, and this is that for so many, because strangers are, almost by definition, strange. Having a few dependable go-to lines for various situations can give you the confidence to move through strangerland more easily and therefore more happily, and that’s not even counting the positive impact on the locals you connect with, which is the real cheek in this tuna.
After a decade of chaos and fear fueled by Trump and Covid, we’re all at least a little bit broken, and everyone needs and deserves as much grace as we can possibly muster. So consider this my contribution to community building, as least for the month of June 2026. Overly long intro? Check. Okay, on with the tips.
For when you’re on the phone with customer service. If you have even a moderately hard-to-pronounce first or last name, spell it first. Most customer service folks are professional people pleasers, and so will take an earnest stab at pronouncing names like Kronstadt and apologize either immediately before or after. That’s when I strike: “That’s okay, I mispronounce it too sometimes.” I will never pretend that’s a particularly good joke, but it has also never failed to get a laugh, and my sample size is statistically significant. It makes sense as the last thing they’re expecting is an even slightly self-deprecating joke. And because I’m sure almost all those jobs are an emotional shitshow from every direction, we should all be extra nice to them. Okay, we should all be extra nice to everyone, but I’m convinced that joke has been retold at dinner tables from Manila to Mexico City. If your name is too easy for this, I find asking “So, where in the world are you anyway?” is a nice overture. Somehow the wording renders it playfully inquisitive and way less stalker-y than “Where are you?” If that goes well you’re going to want to go straight to whatever weather difference or similarity exists between your two locales, but please don’t. Resist the easy high of weather banter and the impulse to compare and/or contrast, and instead connect, even if you have to make up a trip you never took to wherever they claim to be. This is good thinking-on-the-fly practice, and if you fuck up it doesn’t matter because they have to be nice to you. That little extra effort, will, I promise, make you feel better for the rest of the day.
For when you’re making any in-person purchase. If you can afford to, pay with cash wherever and whenever possible. This not only forces a more intimate physical interaction but allows you to ask, “Do you take cash?” This is such a lame joke that often people don’t immediately recognize it as a joke, but I’m very good at forcing the issue with a pregnant pause or slight eyebrow raise. Then a good laugh is had by all, often followed by a discussion of the dizzying pace of change on planet Earth. The happy shrapnel of this approach is it’s hard to get into serious credit card debt if you pay cash for everything. I should mention it doesn’t count if you’re in person but the other transactioner is mechanical, even if you speak for both. Like ATM visits don’t count, nor do those creepy places in basketball arenas where no one works but you can still get a beer and those even creepier Amazon stores I would never go into. When the robots talk we can talk, but until then the connection doesn’t count unless both sides are homo sapiens.
For when you’re walking into a building. If you see or sense someone far enough behind you that it would be just a little weird for you to open and hold the door for them, you should definitely open and hold the door for them. This one I suppose could be fraught with peril depending on who and where you are, but I like to envision a world where that isn’t a thing and so I think it’s at least worth considering. The other thing that works in this realm is the “Oh no, after you” dance you might chance into once in a great while, and it’s always fun but its inherent spontaneity makes it much harder to choreograph. When you do hold doors for people, which you should if you can, there are any number of stupid jokes that are so unexpected they register as funny. “No tips please, I just really love doors,” “Please keep smiling, I’m being graded on this,” and “I’m embarrassed to say how many times I pushed on this sucker before I figured it out, and now I’m just paying it forward,” are just a few of my favorites. Generally speaking whatever feels right is fine, but in my experience, if I wonder at all if something is okay to say, it probably isn’t.
For when you’re someplace you go often enough to recognize the faces of people who work there. Ask their names and tell them yours. It’s so basic it shouldn’t work, but it does. Everyone wants to be seen, and sometimes—understandably, as so many are struggling—we don’t see the people who are behind the counter, or who bring us the things we ask them to bring us. And if they sound like they’re not from the US, ask them politely how the hell they wound up in the exact spot they’re in, and glory in the long odds they likely beat to get to a place where you get to nose into their lives in this way. I played golf today and met Luis, my first Paraguayan pal and just a delightful human being. Golf courses prefer foursomes, and so me and my two pals shook hands with Luis and introduced ourselves. I haven’t played enough golf to know, so I suppose it’s possible to not engage the new guy in conversation, but that’s just not how I’m wired. After a few pleasantries I went with “Do you mind if I ask where you’re from?” and off we went. Of course because it’s DC he’s only two degrees separated from someone I’ve been close with for almost 30 years. It was such an easy entry, but if I hadn’t asked I would have missed out on a very nice guy with a terrific story.
That seems sufficient for now. I should add I think this topic is so important I don’t even mind the Post and Times trying to steal my shit, although I do wish they would do theirs better and leave mine alone. And I always respond to groundswells of support for sequels, or I think I would if that ever happened. In the meantime, if it’s at all in you, the next time it feels really safe and smiles have been exchanged, open your mouth’s door and walk out. And cheat sheets are not only allowed, they’re encouraged.
