Chatting With Strangers: Why it’s Worth the Awkwardness 

I was sitting on a two-hour train ride, sulking in the misery of having forgotten my headphones for the day. Nothing worse could happen to a girl who relies on public transportation. To entertain myself, I tried to subtly people-watch those around me. I started listening in on the couple sitting across from me. They were holding hands and talking about how fast they’d had to run to catch the train. I caught the woman’s eye, so I smiled and told them I’d barely made it myself. 

We ended up making some small talk, and after a few minutes, the conversation turned to their relationship. They’d been living together for a while, and they recently adopted a dog. I knew it would be an intrusive question, but I was feeling curious, so I asked if they were interested in having kids. It would’ve been completely reasonable for them not to answer that question, but instead, the woman just said, “We’ll probably never see you again, so let’s talk about it.” 

She told me that she wanted kids, but he wasn’t so sure. He explained that he’d felt hesitant when they were deciding to adopt a dog, and then he did end up feeling overwhelmed with the experience. He just didn’t like it as much as he’d hoped, and feared the same thing could happen with a kid. The woman thought a baby would be different from a dog, but I told them I thought it could be representative of what he would be like as a dad. You never actually know what your kid is going to be like. While I’m sure you’d love the thing no matter what, there is a good chance you might not really like it. And once you’ve committed, you can’t really back out.

Essentially, I was telling this stranger that his relationship with his dog might mean he’d be a bad father. And both he and his girlfriend seemed to really consider my point.

I had no business saying any of that. I don’t have a kid or a dog or any sort of expertise on someone else’s relationship. But they were strangers, and they wanted to hear my opinion, so I was going to be completely honest. I’d never seen a couple speak so openly about their issues while still being so respectful of one another. They never got defensive, but remained completely candid. It was quite inspiring to watch.

I’ve learned a lot from figuring out how to talk with strangers. When you’re chatting to a stranger, you have no shared history or dynamic to guide things. There’s nowhere that the conversation is “supposed” to go, and that leaves you with very low expectations. The conversation can truly go anywhere. Sometimes it’s just small talk, but sometimes you end up in completely unique discussions. You could learn a new fact or philosophy, or bond over a mutual hatred of tomatoes. You could learn someone’s entire life story, or maybe even discuss whether someone’s feelings about their dog say something about their fitness for fatherhood.

Naturally, this requires some willingness to put yourself out there. One of the bigger fears when learning how to talk to strangers is simply that it’s going to be embarrassing. We worry that we’ll say something stupid, or run out of things to say, and it will just be awkward. This happens far less than people expect, but more importantly, it’s okay for things to get awkward. It can be quite healthy to embarrass yourself, and what better way to do that than with a complete stranger? The stakes are so much lower, and the embarrassment fades so much quicker.

We spend a lot of time trying to avoid this feeling, but it’s just making us and our lives a whole lot more boring. It’s okay for conversations to be clunky and strange; they’re more enjoyable that way. Most of my memorable interactions with strangers involve me saying or doing something embarrassing. If you’re trying to avoid any type of embarrassment, you’ll just end up having sterile connections. And you likely won’t completely avoid embarrassment. You’ll just take it a lot more seriously when something embarrassing inevitably does happen. I think being willing to embarrass yourself is what makes other people trust you. It shows that you’re not performing and that you are actually present in the moment. 

Of course, there’s a bigger fear when talking to strangers—you don’t want to put yourself in a sketchy situation. And of course, not everyone approaches these interactions from the same starting point. The social contract when talking to a stranger varies depending on the cultural norms you are around. In some places, striking up a conversation is totally ordinary, in others it’s suspicious, and in others it’s unsafe. If someone approaches you, it can be hard to tell if they want something from you or if they’re just being kind. You have to keep yourself safe in these situations, but I still think it’s worth it. So, here are some of my tips on how to talk to strangers:

The biggest thing is just staying centered. If you’re on edge it really won’t be that enjoyable, and it’ll be a lot harder to read the situation clearly. Anxiety makes everything feel more threatening than it is. That’s not very useful when you’re trying to figure out if someone is safe to be talking to. There’s nothing wrong with feeling anxious, but you want to make sure you’re slowing down and checking in with yourself. Your instincts work a lot better when you’re not drowning them out with panic.

Having a general understanding of what you are or are not willing to say helps a lot more than you’d think. In the moment, it’s usually harder to know, so think ahead a little. For some people, it’s really liberating to talk about something personal, to maybe even share a secret with someone they’ll never see again. For others, that’s too vulnerable. Both are just good things to know. If you know ahead of time what you’re more or less comfortable with, it can make it easier to avoid certain topics. While I love getting into a deeper and more honest conversation with a stranger, a lot of the time I’m more interested in discussing opinions than sharing personal details. It depends on the day, honestly. And that brings me to my next point: Lie. 

I know I just caused a whole ruckus about how honest you can be with strangers, but also, lying to strangers is awesome. Often when I’m chatting with someone random, my name is Chloe, and I have a boyfriend. In fact, the second you give me a bad vibe, my boyfriend is actually on his way. It’s an easy out, and it isn’t hurting anyone. (And let’s say, theoretically, you end up really connecting and wanting to be friends with this person—you tell them you lied, and you both laugh about it. No problem. They were a stranger at the time, and you really don’t have much of an obligation.)

Knowing how to gracefully exit a conversation is the last thing worth mentioning, and it’s pretty simple. I used to be nervous when talking to strangers because I didn’t want to be awkward or rude when I felt the conversation was done. But it truly isn’t that hard. I usually ask someone what they are doing with the rest of their day, tell them I have plans with a friend, and say it was lovely talking to them. Phrases like “it was so nice to meet you” or “I hope you have a great rest of your day” are pretty widely understood to mean goodbye. And that’s really all you need.

Knowing how to talk to strangers makes you so much more open to the world around you. I don’t need to explain all the ways that community is lacking nowadays (COVID happened, our generation forgot how to socialize, we’re too addicted to our phones, blah blah blah), but talking to strangers really does help with that feeling of disconnection. The whole thing is a skill—knowing when to ask the weird question, when to make small talk, when to lie about your name, when to just say it was lovely meeting someone, and walk away.  And it’s a skill very worth developing.

A lot of these conversations won’t be particularly profound or memorable, but every once in a while, they give you a really interesting story or new perspective that you’ll remember for years. I think I’ll remember that couple I spoke with on the train for a long time. I’ll wonder if they decided to have kids, or how their dog is doing. I’ll never know, and that’s part of what makes it so fun and worth remembering. So go talk to some people, and please, be a little awkward and embarrassed about it.