4 Ways to Start Conversations with a Stranger

Starting conversations with people I have never met is like my superpower.

I’m not really sure how it happened. I think I am just short enough to not be threatening, just polite enough to not turn people away, just handsome enough to look approachable, and just bearded enough to look wise.

In the past year, I have met:

  • A Roller Derby team from Minnesota whose captain is married to a heavy metal singer
  • A doctoral candidate from Kansas who also freelances in how-to training videos because “teachers get paid shit and that other stuff is really easy.”
  • A girl who deleted all the apps (including the email one) from her phone because she was “tired of the drama”
  • An older couple who have written two books together and whose “retirement” plan is this product, a badge which measures if you are getting enough vitamin D during the day. (That website looks a lot better than it did when they first told me about it, so things must be going well)

Other than “looking completely average,” here are the tangible actions I take to start conversations with aliens. I mean strangers.


Silence is awful. It’s so weird. Like the two of you are sitting in the same spot for an extended period of time. What if you miss the grace period to say hello and then you’re stuck in an airplane side by side for hours?

With every second that ticks by, the pressure builds to say something. After a while, it’s far too late, and you are trapped in an endless cycle of avoiding eye contact, coughing uncomfortably, and suddenly becoming very interested in perusing the Skymall catalog.

“Oh look,” you’ll think to yourself, determined to not shift your gaze away from the page. “I didn’t know they made remote controls shaped like Harry Potter’s wand.”

There is absolutely NO chance I will be the second one to speak. Even if it’s just “Hello!” that takes the pressure off the other person.


The first one is going to be scary.

You’ll walk up to someone and your heart will dive into your stomach, your throat will tighten up, and your tongue will forget how to make words.

But, just like everything, it gets easier. I try to talk to one new person a day. I rarely want to, so I have to frame conversation like this:

I know nothing. Other people know something. By talking to new people, I can know a little more than nothing. By keeping to myself, I will remain ignorant.


I have a friend who hates small talk. She can’t stand how meaningless it is. Not surprisingly, she also has trouble meeting new people.

Here’s the thing, though — Small talk is a necessary entry level play for making people feel comfortable. It’s the basis for everything, even if it seems banal. I realized most of my small talk (when travelling) is pretty much a variant of this script:

Me: “Woo, man, I can’t believe this [STATEMENT ABOUT THE WEATHER].”

Stranger: “Yeah, it’s crazy how [CONFIRMS STATEMENT ABOUT WEATHER].”

Me: “For sure. Is [PLACE WE ARE GOING] home for you?”

Stranger: “Nope, I’m from…”

Small talk really is obnoxious. Actually, there are several co-workers who have only ever conversed with me about the weather or the day of the week and it’s proximity to Friday. The goal, then, for me is to build an easy springboard from small talk to revealing a simple personal detail.

Once someone opens up even the slightest crack into their personal life, you can move on to:


Okay, so now I know the person is from Boston or wherever. I ask if they like it there. Then I’ll ask about their kids. Then I’ll ask about something else.

Every time someone trusts you with a detail about themselves, nod and smile and ask for more. Each sentence is going to be a wealth of new information. Ask about the new stuff. It’s a game, really.

“But Todd! What will I say next? What if we run out of things to talk about?”

You won’t if you keep asking questions. I have noticed people always have plenty of problems or passions or both.

What they don’t have is someone to listen to them.

Much love as always,

— TB

This was originally published on Medium by Todd Brison – author of THE CREATIVE’S CURSE here: toddbrison.com/buythebook

See also: The Ultimate Survival Guide to Not Fitting In

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