We’ve talked about taking vacations alone and living alone, but what about walking around town by yourself? When you’re flying solo in public, do you talk to strangers or keep quiet? This week, just for fun, Cup of Jo editor Caroline—who generally stays mum—ventured outside of her comfort zone and chatted with various strangers around NYC. Here’s Caroline’s diary…

By many definitions, I am an introvert. While this can come with its share of challenges (feeling awkward at parties, being mistaken for aloof), I mostly enjoy it. Since I’ve spent 12 years in New York, it’s second nature to feel comfortable in a crowd of strangers. I love reading books on the subway, taking meditative walks or eavesdropping (in the least creepy way possible) on random conversations.

I’m not shy, but when approaching humans in the wild, what would we talk about besides the weather? (I know it’s cold, you know it’s cold…let’s get down to something more interesting, shall we?) But! Is it possible I’ve been missing out? Would chatting with strangers yield more friends, more insight, or at the very least, more interesting stories? So, urged by Joanna—who talks to everybody, wherever she goes—I set out to converse with the folks I encounter in my everyday life. Here’s what happened…

At the coffee shop (Saturday, 9am):
The barista wears the most fantastic earrings—long turquoise drops that graze her shoulders. “I love your earrings!” I trill. “Thanks!” she says, and immediately turns her attention back to tidying the pastries in a nearby case. Conversation over. Initial attempt failed.

Walking the dog (Saturday, 7pm):
Talking to fellow dog owners is (I would assume) the equivalent of parents chatting at the playground. You’re outside, you have something in common, the words flow. Yet, funnily enough, dog owners often address only the dogs—usually in a baby voice—without acknowledging each other. This time, I make a point to focus on the human, and thus meet Helen, who lives down the block. Despite my best attempts at friendliness (“How are you?” “Such a lovely night!”), Helen continues to talk directly to my dog using a sing-song tone. “I am a person!” I want to say. Instead I pat her corgi’s head and continue on my way. Whatever. We chatted, kind of.

On the subway (Sunday, noon):
I spy a twenty-something guy—he looks nice, if a little spacey, sort of like a kindly sheep. “Hi!” I say, sitting next to him on the crowded train. We exchange pleasantries and he launches into a story about his living situation (a bevy of kooky roommates) and job (parking cars in a swanky Upper East Side garage): “I’ve driven Lamborghinis, Maseratis, Porsches, Ferraris…” Everyone is staring at us; we’ve become a sideshow. “How old are you?” he asks. Oh boy. “How old do you think I am?” “Umm… 22?” he guesses. Older. “23?” Older. He guesses all of the numbers up to my current age, at which point his eyes grow wide. “You’re 30?!” he gasps, “Wow, that’s old!” I exit the train with 8,594,783 new reasons that I do not like chatting with strangers.

The next day, I report back with my bleak findings. “You just haven’t talked to enough people,” Joanna says. Well, yeah…but at this rate, do I really want to? Nevertheless, my quest must continue.

At the nail salon (Monday, 8pm):
Post-manicure, the spirited fifty-something woman next to me (drying her glittery pink and turquoise nails) makes “tut, tut” noises as news headlines flash across the overhead TV, each more horrifying than the next. We bond over the apparent state of humanity (bad), the state of the world (scary) and the upcoming weather (mostly good). Our easy conversation continues all the way through our mutual drying time. She hugs me farewell, then waves like an excited child all the way down the block. I love her! I love people. Why can’t everyone be this nice?

At the deli (Tuesday, 1pm):
“Can I help you?” shouts the guy behind the counter, when he hears the door jingle. He pauses. “Is anybody there?!” He can’t see me over the extra-tall chip display towering on top of the glass case. Not exactly the best way to begin a conversation. When he finally spots me, I order a sandwich, and as the bread toasts, I ask how his day is going. He looks happy that somebody asked. “What’s your favorite thing on the menu?” I inquire. He scoots off, then re-appears, beaming and wielding a sample. Did you know that tuna salad tastes delicious with cranberries and apples mixed in? Well, it does.

In a cab (Wednesday, 6pm):
It’s the end of the day and the sky threatens to rain, so I break from my usual routine and splurge on a cab ride home. “How are you today?” I ask the driver. “Oh, you know…tired.” As we continue talking, I hear about the many places he’s driven and how much he’s looking forward to going home. As we pull up to my building, the meter does something funny and my total fails to show on the screen. “You know what?” he says, “You’re a really nice lady. You’re the first nice person I’ve picked up all day. I don’t want to charge you.” He gives me a ride for free! This has NEVER happened before. As it turns out, talking to people is great because you get free stuff. Just kidding! Sometimes you actually manage to brighten someone’s day. And that, in the end, is always worth it.

In the park (Wednesday, 7:30pm):
Later that evening, I’m sitting on a bench on the Brooklyn waterfront, next to a sweet elderly couple sharing a newspaper. “Do you want to read your horoscope?” the husband asks his wife. “You know I do!” she says, swiping the page out of his hands. They’re so cute, I think, wondering what their stories are. But I don’t try to talk to them, content to eat my dinner against the hum of their comfortable banter. Old habits die hard, I guess. But sometimes that’s okay.

I’m curious: Do you talk to strangers when you’re at movies, in shops or waiting in line at the grocery store? Or do you prefer not to say anything?

P.S. More posts from Caroline, including a lipstick challenge and thoughts on natural deodorant.