This Will Be the Year I Talk to More Strangers

Photo-Illustration: by The Cut; Photo: Getty Images

I normally operate on the assumption that everybody wants to be left alone. I keep emails short and sweet. I carefully consider how many words I really need to order a coffee. I apologize for bothering people too often. This means I don’t initiate conversation with strangers unless it’s absolutely necessary. Why would I disrupt someone’s podcast on the train just to ask where their jacket is from? Nobody wants that. Unsolicited interactions in public have always seemed annoying, tone-deaf, even invasive.

While I still pride myself on my abbreviated email skills, I’m starting to question the “talking to strangers” part of this attitude. It began with my boyfriend, who, as I learned shortly after we started dating, has a habit of striking up a conversation with any stranger who happens to catch his eye. To me, this was embarrassing. Was I dating a weirdo with no aptitude for social cues? But what I saw as accosting baristas trapped behind a counter with small talk, he saw as friendliness, and after several months of observation, I had to admit that he was largely right. People are usually happy to chat, and they’ll make it pretty clear if they aren’t. My theory that everyone is secretly waiting for me to stop talking to them so they can peacefully go about their day suddenly had a lot of holes.

Of course, it’s not nearly as easy for me to replicate his success — not only do I lack the advanced social skills it takes to smoothly slip in and out of a conversation, it’s not always safe for some of us to suddenly start talking to random guys on the street. I’ve learned some necessary guidelines when it comes to chatting up strangers. You have to involve yourself assertively enough to get their attention but not so aggressively that they’re alarmed. You have to give people a chance to end the exchange if they so choose. On the flip side, you have to bear in mind that you might get sucked into a longer conversation than you’d wanted. I’m nowhere near mastering all this, but I plan to practice.

When done carefully, I’ve found that a few extra minutes of low-lift socializing does me a world of good. There are material benefits: Any of my boyfriend’s friends will tell you that he has been getting free pastries since he could talk, thanks to his knack for befriending café managers. In general, people are a little more willing to offer favors if you’ve just had a three-minute chat about their hand tattoos. And I’m getting extra help in the style department: Last week, I spotted the perfect going-out bag at a party and, instead of silently pining over it, I asked its owner where it was from. Have you ever crowdsourced your closet on the streets of New York? You might want to try it. I’m told there are a lot of fashionable people here.

But my newfound boldness is helping me in deeper ways too. I’ve found these exchanges to be strangely fulfilling — like mini-hangs that punctuate my day. Instead of an hours-long investment in socializing, I get a little hit of connection without ever needing to join a group chat. I’ve always thought of myself as pretty shy. I spoke so little as a kid that my preschool teachers sent me to get a hearing test, and as an adult, I’ve never really felt like I mastered the whole “putting yourself out there” thing. I spent the past year finding socializing more performative and exhausting than ever. But posing as someone much more outgoing has reminded me how good it can feel to talk to other humans — even if it’s about nothing. Turns out even small talk with strangers can be rewarding.

With that in mind, I’m heading into the New Year with the belief that, actually, bothering people is maybe sometimes okay. Even if it’s not for you, you might just get a free latte.