Relationships

“Hello, Stranger!”

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.

  1. I would love to hear more of Caroline’s writing — she’s honest, relatable and funny. :) Pleasantly surprised with this post!

  2. “when approaching humans in the wild” … made me laugh!

  3. In Portugal is pretty common to talk to strangers on the streets or comment stuff :)

  4. oh this was a fun read! im also an introvert but sometimes I do let a stranger know I like their skirt or bag or….its hard to break the ice but because you dont know them or they you, it makes it easier somehow…

  5. I loved this post! It was such a good read!
    It is interesting to hear the difference between how people reacted when talking to strangers. For example the difference between the elderly lady that hugged you goodbye and the man that told you being 30 years of age was old!
    I really enjoyed this post, great work!!

  6. What a great post! After reading your different conversations with strangers, I realized that I pretty much talk to strangers all.the.time. Ha! I thought I was a little more shy but I guess not.

    Keep the great posts coming!

  7. I love this post! I read somewhere that making small talk with strangers leads to more happiness. I’ve tried it and I think it works hoping that you bump into those nice people of course!

  8. This post made my day! Just the afternoon pick-me-up that was needed. Thank you for sharing and restoring my faith in humanity! :)

  9. This is so funny! I live in New Orleans where is it considered rude not to say to everyone you pass on the street. I have to budget extra time in when I walk my dog in the morning so I can catch up with the neighbors.

    I think this should be series you do in different cites.

  10. what a great read. I have a happy feeling from reading this. I was also going to say what a lovely fun girl Caroline seems but everyone has said that and i don’t want her getting big headed!

  11. Great post! I only talk to strangers in two types of situations: at the airport and on a plane. The person who sits next to me is in the ‘hot seat’ as talking distracts me from my fears of flying. Oh! And whenever I hear an American accent in London… as an expat, I haven’t yet gotten over the need to know that person’s past and what got them here – like me!

    We should really talk more I think – its so wonderful to meet people of different backgrounds.. I met a wonderful woman waiting for a plane (Toronto to London). We then had a delay, and she took me to dinner. When I went to pay, she wouldn’t let me, saying ‘do the same for someone else’. What wonderful people we have in this world! x

  12. Caroline, you are brilliant! I love your writing style.

    I’m also an introvert but I think talking to strangers is a cultural thing. In South Africa, people tend to be more friendly to each other than I have noticed in other Western countries (US, UK, Europe etc). And if you’re pregnant or have a little one my GOODNESS, expect everyone to chat to you, especially older ladies (and often give unwanted advice “You MUST be having a boy look at that round belly”) ;)

  13. Great post. Sometimes I think we are losing our good habits. My parents and their generations, talk a lot with people. We don’t have to be “scare” to talk to others. I love people, and learn new things, make someone smile. It’s so easy. We should do it everyday ;)
    http://tarragonain.blogspot.com.es

  14. Caroline’s 30? No way! I second other readers… I wanna know your beauty routine!

  15. I am an introvert, but a high-energy introvert which is why I don’t think I realized this until later in life. When I was growing up, I never let the chance talk to anyone and everyone pass me by. It was a lot of fun and I met a lot of really interesting people. I was known for being very friendly and was always pegged as being an extrovert. Now that I have 5 kids, it’s a totally different story. There is not much solitude to be had in my day-to-day life and now I rarely talk to strangers. I think that if I have a quiet moment to myself, I treasure it. Which is why I have also been known to go the other direction when I see someone I know in a grocery store. But I have to say that I am looking forward to the day when I have more time to recharge my batteries and I’m hoping that my once extra-friendly self, makes her way out into the world again.

  16. I *love* talking to strangers. And sometimes I don’t do it verbally! Sometimes I send mail to strangers, and even more often than that I make guerrilla art installations that I ask people to participate in on the street. So I get to have artful conversations with strangers even when I’m not there.

  17. I like to strike up conversations with strangers, if it feels like the right time. Like, the other weekend, my husband and I were at this dinner thing and this lone man asked if the seats across from us were taken. We said, “no,” and he sat down. It would’ve felt more awkward to not say anything to him, so I started a conversation and we all seemed to have a blast the rest of the night.

    It’s a great way to meet new people! :)

  18. This is such an interesting experiment! Personally, I never talk to strangers. Oddly enough I often think something like: “Wow, that skirt looks so good on her. I should tell her!” but then I chicken out of it.
    It is weird, because everybody likes a good, honest compliment, but still there is some kind of an internal barrier I have yet to overcome.
    But it is nice to see how positive this experiment turned out for you in the end. Apparently there are still some really nice people out there :)

  19. Caroline, what a sweet and honest post :-) I loved it ! Joanna made a good decision with hiring you.

  20. Oh something else, every single day almost I pass the same girl about my age on my way too and from work in the morning and at night. She lives two doors down from me. I always try to smile at her or catch her eye to say hello but she purposely avoids it… :( and im sure she recognizes me too!

  21. One of my favorite posts on this blog in a while! Definitely an interesting though. I’m quite chatty and love talking
    And meeting with new people. I always look at people on the train on my way to work (in Chicago) and I want to know their stories. However, most people just don’t want to engage with strangers, or so it seems! I think in big cities people are also afraid of meeting weirdos or someone that might assault you!

  22. Caroline sounds just like me. I’m a “Only Speak in Public when Spoken to in Public” type of girl. I’m always willing to give someone a smile or a nod but I’m never the one to initiate conversation. Maybe it’s a strange way of showing a fear of rejection or somethingt.

    But, heck, people are just people right! And YOLO! (Or something). Why not get to know as many people as possible and hear as many stories as you can in this life, right?

    You go, Caroline! Way to be bold! It inspires me to do the same!

  23. I’m from Charleston, SC. I had culture shock when I moved “up North” (DC) & people didn’t greet/wave/chat/call each other Sugar :)

  24. Well done, Caroline, on going out of your comfort zone!

    Even though I’ve lived out of the US for over 10 years, I find that I still don’t know exactly what “I am” in this environment. For the most part, I’m very much a local person. But never 100%, unless I’m with a really close friend.

    That said, I find that I can more easily go with the feeling at the moment. I often speak to less people than I probably wou;d if I were in the states. But I also find that I’m more easily able to speak to people of other cultures than your average Dutch person. I automatically have something in common with them. It’s oddly comforting at times.

  25. Caroline the bold! This post is absolutely refreshing. Way to go!

  26. Like most who have posted comments here, I’m an introvert who has learned to love talking to strangers.

    But what I really think is interesting is that this is the usual “experiment” and that almost never do we challenge extroverts to behave more like introverts….

  27. This made me laugh. I like Caroline’s perspective. I fall somewhere in the middle–happy to talk to strangers, but I don’t always engage. Maybe I should more often?