How to Talk to Strangers

I’ve said this many times, but one thing I love is a good awkward situation.  I mean, they make for great fodder for the Modern Manners Guy column, of course! True, it’s very unnerving when an awkward situation happens, but I always tend to value the take-away from the situation much more than I dread the weirdness.

However, I do have my limitations. If a stranger who approaches me turns out to be a legit lunatic and picks me as the lucky one who gets to hear their rant about the government conspiracy to hide aliens, that’s never fun… Although I am intrigued…

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However odd, weird or uncomfortable talking to someone you don’t know is, I find that being able to kick up a conversation with a complete stranger is a skill that everyone should have in their back pocket. You never know when that person next to you could be someone crucial to your career or life. Maybe they’re even your soul mate! Or maybe they will offer you helpful directions if you’re lost.  

So, before you find yourself lost for words about talking to someone new, check out my top 3 Quick and Dirty Tips for properly starting a conversation with a stranger:

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

Tip #3: Have a Great Opener

In business, we use the term “elevator pitch” to describe a quick 15-second sound bite that explains your idea, business, or product. It’s also a way to quickly showcase who you are and what you’re about. A great pitch is key to any successful conversation and for most people, the length of the elevator pitch is how long it takes to make up their mind about whatever you’re saying.

When talking to a stranger, this has to be something you’ve mastered. The opener is what you decide on using after you choose A) who you should talk to and B) when (or if) you should talk to them. The opener is a quick, rehearsed pitch and intended to attract. And I don’t mean in a romantic way either. Talking to a stranger is not always about hooking up. You may need directions someplace or just want to converse with a like-minded person to kill time.

The key to a great opener is picking out something you feel this person is looking for or can relate to. For example, the guy at the train station was clearly just looking to get lucky. Had he stepped back and read the woman a bit better, he could have seen that she was frustrated and maybe wanted some commiseration. Something like, “Ugh, nothing is more annoying than when the station doesn’t let us know what gate we’re at until 30 seconds before! Right?”  This is much more innocent and relatable than, “Sure is hot in here. Want to get a drink?”

Another situation when you may need to talk to strangers is if you need some assistance. In this case, go with flattery, “Excuse me, you look like you know your way around this place. Can you help me find XYZ?” If you just want to shoot the breeze and get through the time, try to find something neutral to start the conversation with, such as “I have to admit, I love summer but the heat this past week has been brutal. Am I right? I can’t wait for Fall to come.”Talking to strangers is something you’re going to come across in life and you shouldn’t fear it. I don’t recommend chasing it, but you never know when thinking on your feet and meeting someone new may come in handy.Do you have a great story about how you kicked up a conversation with a stranger?  Post all the details in the comment section below.

As always, if you have another manners question, I look forward to hearing from you at manners@quickanddirtytips.com. Follow me on Twitter @MannersQDT, and of course, check back next week for more Modern Manners Guy tips for a more polite life.

And if you have any recent graduates in your circle, or perhaps someone who is looking to start a new career, check out my new book, Reply All…And Other Ways to Tank Your Career. It’s available for pre-order now!