Break the Ice: or How I Learned to Talk to Strangers

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It’s summer, it’s July, and according to my friend on the subway this morning, we’re in the middle of a heat wave here in New York. Normally this would be reason enough to clear out the convenience store freezer of all their ice, fill the bathtub with it, and get in. Instead, I want to talk about something just as refreshing and, potentially, painful: breaking the ice with strangers (that’s masterful segue work if I do say so myself).

I don’t know why it is–though I’m sure there’s some scientific explanation–but the summer months bring out a new vigor in us. We spend more time outside, go more places, and do more things - we even tend to spend more money. So much so that on a nice summer day, it’s impossible to ignore the throngs of people milling about outside. Which brings me to this question: How often do you stop and chat with these people? Every day? (ok, show-off) Once a week? A month? A blue moon? I would imagine that it’s somewhere between once in a blue moon and never, and that’s unfortunate. Not because I think we all need to be interacting with each other at all times. No. It’s sad because ignoring our human surroundings not only secludes us from those surroundings, but also means we’re missing innumerable opportunities to connect with someone, even if it’s only for 15 seconds.

Let’s try something. You and me, together, are going to push ourselves out of our comfort zones and interact with our surroundings at least once a week. Don’t think you’ll be able to come up with the witty comment to make the other person laugh? Don’t fret. The witty comment is over-done and you can do so much better than that. Watch (read) and learn.


Don’t forget what I just told you. Write it down, memorize it, and write it down again – the witty comment is over-done. It doesn’t work, or qualify as witty, if everyone and their mother does it. Try this instead: Go up to a person you may not know and strike up a genuine conversation.

Let me tell you a little story: I was walking back to my apartment from work not long ago when I saw someone stop and read the menu posted in the window of a restaurant. For some reason I had a desire to talk to this person so I simply walked up next to her and told her that the food at that place was delicious. She asked a question, I answered, and we went our separate ways. Simple.

When it comes to interacting with others, we often over think it and shy away because we don’t have anything memorable to say. You don’t need to have anything memorable to say. You just need to have something to say. (Note: this applies for people of both sexes.)


Whether you’re trying to hit on someone, or just strike up a convo with the person sitting next to you in the park, carry yourself like you’re doing it because you want to. Nothing makes an interaction fizzle faster than apprehension or timidity. Look the person in the eye, introduce yourself (say your name, or talk about the weather, you know, the usual) and tell that person what you want to say. It doesn’t have to be profound or thoughtful. It could something as innocuous as “nice shoes”.


You’re going to have at least a few awkward encounters. The other person may not be as open to the interaction as you are, or they may not have heard you, or they ignored you, or y’all’s chemistry simply didn’t mesh, and the interaction was doomed from jump. Don’t fear that. It’s going to happen. It’s inevitable. Use those awkward interactions as learning experiences and work toward improving these interactions in the future. Plus, awkward situations lead to hilarious stories for your next encounters.


This is the simplest thing to say, and the hardest thing to actualize. Too often we try (operative word: try) to impress the other person and the more we try to impress them, the less we’re ourselves.

People are either going to like you, or they’re not. Not everyone is going to pick up what you’re putting down so don’t be disheartened if–and when–your hilarious, yet somewhat distasteful, one-liner isn’t volleyed back to you. That person wasn’t jiving with you and that’s ok because in reality, if you like you, why would you want to be interacting with someone who doesn’t. Brush it off because chances are, one of these days you’ll have an awesome random encounter with a stranger. It could last 15 seconds, or blossom into a friendship, but it’ll be awesome nonetheless.

Until next time – hi, my name is Arye.

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When Arye isn't helping optimize your time, he is doing his part to ensure life is full of shenanigans.