How to Talk to Strangers

Have you ever wanted to approach a stranger and kick up a conversation? Whether you're at a networking event, lost and need directions, or have your eye on a special someone - there will be a time when you'll want to talk to a stranger. How to pull it off without looking like a weirdo? Try Modern Manners Guy's tips.

Richie Frieman
6-minute read
Episode #255

Tip #1: Choose Wisely

As I said, not every stranger out there will be a super cool individual who you'll connect with.  Nor should you chat with anyone at any time. Let’s make one thing clear: they're strangers! Not friends...yet. I mean the root of the very word stranger is "strange," so be sure to remember that when you feel the urge to talk to someone you have never met before.  For example, if I'm at a networking event, my main goal is to make valuable connections. I'm not going to pick on an unsuspecting waitress or the event planner to start a casual chat. I'm there to talk to someone who is connected in my industry. So how do you choose wisely?

For starters, wherever you are - at an event, a bar, an airport lounge, wherever - survey the room to figure out who looks like someone you should speak to. Now, some of you may say that it's wrong to judge people by how they look or dress. And you're right. But it is the only thing you have to go on when you are randomly picking a complete stranger to talk to. Never pick someone who is already talking to themselves, like that dude who sits outside a 7-11 singing show tunes in ratty sweatpants (sans shirt and shoes). That's red flag número uno.  

As well, don't talk to someone who is on the phone. You can't bother a stranger who is clearly busy with something else. Find someone who looks like you may have something in common to use in your discussion. For example, maybe you are the only two young people in the room of much older colleagues? Or, as happened to me, I had the same messenger bag as someone sitting next to me at the train station, and that's never happened before. So we had something to talk about while we were waiting. If you start a conversation and notice that the person doesn't look you in the eye and seems uninterested in a chat, move on and pick someone who at least looks like they're not having the worst day of their life.

Tip #2: Timing Is Everything

True story: I was on my way back from a trip to New York where I traveled to record the audio version of my new book Reply All... And Other Ways to Tank Your Career, I witnessed a young man attempt - and fail - to pick up a girl while waiting for the train. For one, this guy did not know her, I could tell that right away. And secondly, call me crazy, but Penn Station in the dead of summer doesn't exactly scream romance. Everyone is sweating from battling the crowd, we’re all waiting to hear our rail announced, and we only care about making the train before it takes off without us. So Don Juan of Penn Station may have been off the mark on this one.  However, it didn't stop him from trying. He sauntered over, dropped his best pick up line…and got nothing in return. The girl, clearly annoyed at something else, was now doubly annoyed because of him. She quickly picked up her phone, to make what I’m assuming was a fake phone call (since there's no cellphone reception in the station). Sorry, buddy.

Now, this episode is not about how to pick up people in train stations. (Sorry but I’m still just shocked that anything I did worked on my wife - like the girl from my story, my wife is way out of my league). But this tip is about the timing of starting conversation with a stranger. Timing, in life, is everything! And clearly this girl was not giving off any signs of being approachable. She was visibly annoyed, seemed panicked about something, and was clearly not interested in talking to anyone that day. Her signals were unmistakable, to everyone but the oblivious guy who tried to hit on her.

If you're going to talk to someone you have to find someone who looks like they're in the mood to talk.  You are not that cool that you will win them over if they’re pissed off already.  I bet if this guy just picked someone else who looked more welcoming, he would have at lest had a shot. Surprisingly, sometimes people do want to talk, and that’s when you win. But also know that if you do start to talk to someone and they don't seem to have the time for you, don't push it.

See also: How to Handle an Awkward Conversation


About the Author

Richie Frieman
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