Mastering Conversations With Complete Strangers
Wanna know the truth about this topic? I used to be so socially anxious to be in an environment where I was forced to have a conversation with someone I didn’t know that I would actively hunt for ways to back out of them with a solid (or watery) excuse.
I was once asked to attend an invite-only social mixer for creative business-owners in Hamilton. I knew that I knew 3-5 of the attendees, but of the other 50 or so invited, they were strangers I’d never met.
On the drive across town, I was feeling sick to my stomach. I couldn’t find the place (to my delight). I was this close to turning around and going home and just following up with a lame excuse about why I didn’t make it.
I ended up finding it after all and… I had a great time. It was worth it. When I got home, I confessed to Leanne how stressed and anxious I was about going.
She said to me, “Why were you nervous? You’re so good at talking to strangers.”
And I realized… she was right!
This night was probably 4 years ago now and I think about it once every two weeks. She changed my life and I’ve never felt uncomfortable walking into a social situation ever since. That night, I began taking inventory of the ways I’ve naturally developed conversations with complete strangers (much thanks to my former gig as a wedding photographer) and today, I’m going to lay them all out for you.
Being Introverted Has Nothing to Do With It
I used to blame being shy on my introversion. I realize now it’s irrelevant.
Anyone can learn to talk to complete strangers.
It is not a talent so much as a skill (well, it can be both, and admittedly I probably blur the line, but I believe in your ability to do it). And the even better news is, as far as I’m concerned, this is one of those few things in life where memorizing a few questions and general principles is all you really need to be off to the races.
Of course, I’m going to go more in depth on the philosophies that underly my approach, but if you don’t care and just want to skip ahead to the practical parts, you can (though, I don’t advise it. I wouldn’t write this next section if I didn’t believe it mattered).
But I’m getting a little ahead of myself here. The point is: whether you’re extroverted or introverted doesn’t matter. I’m still an introverted homebody but I can engage in a good conversation with just about anyone (sometimes with a little self-motivating first) in a way that demonstrates confidence.
…Where do you begin learning how to do that?
Situational Awareness
It’s important to understand a few things first if you’re hoping to succeed in master conversation with complete strangers.
1. Not Everyone Cares to Engage
Again, I’m a fairly comfortable and confident conversationalist these days, but not everyone you’re going to come across is going to care to engage with you. You’ll pull out all the stops and get no bites on the line. Pack up your rod and move on with your life. Enjoy the silence and rest easy knowing you tried.
2. Not Every Technique Applies to Every Situation
If you’ve merely stopped someone on the street to ask them which way to the nearest gas station, you probably shouldn’t ask questions about their childhood or dream vacations. It’s just not necessary. While the techniques below are simple in nature and easy to memorize, you’ll need to learn to quickly analyze your particular situation and choose the right conversation tool for the job.
What Makes a Good Conversationalist
This is going to sound counterintuitive at first, but if you can stick with me, I think you might be pleasantly surprised at how easy it actually can be to become good at talking to people you don’t know.
Historically, many different people hold the following to be true (my favourite of which being Dale Carnegie in his life-changing book How to Win Friends & Influence People), and I can anecdotally confirm that the following principle is, indeed, very true.
People will think of you as good at conversation if you ask them more questions so they do more of the talking.
Just… think about that for a second, ok?
People will think you are good at conversation if you just ask questions that make them do the talking.
Well, if they’re doing the majority of the talking, that’s a little less of a conversation and a lot more of a Question & Answer, isn’t it?
You bet it is! And that’s great news to anyone who wants to start having great conversations.
To the best of my recollection (and without a source to back me up, so believe at your own risk), it’s been scientifically proven that people will leave a conversation with you feeling like it was a positive social interaction—and that you are a good person worth being friends with—if you simply get them talking.
That’s madness! But so exciting if you are here to learn how to talk to strangers with confidence. Cool.
This principle, of asking questions and making people do the talking, is basically leading me into one of the most important aspects of my technique (if you could be so bold as to ascribe me any of the credit for what I’m sharing).
Good conversation is about finding common ground with a person. It’s about relating in some way, even if only indirectly.
All of the very practical tips we’re about to dive into all draw back to this principle of conversation: we are exchanging information with people, quite often about something that is of a personal nature to us (I mean, even if we’re just talking about history, it’s personal to us if we’ve taken the time to learn about it, so by that standard, anything is personal), and trying to see where we can relate over those shared experiences.
It’s why icebreaker group activities (which have a horrible reputation but are more effective at laying relational foundations than people want to admit) are so useful. Even if the only thing you’re united about is hating icebreaker activities, the organizer of the event wins. They’ve succeeded at their goal of bringing you together. (Think about that the next time you’re forced to participate in an icebreaker. No matter the outcome, you can’t win [or rather, everyone wins].)
Aidan’s Techniques for Starting Conversations
Generally speaking, my approach to conversation with people is simply to ask a ton of questions. Get the other person talking. If my goal is to generate conversation, I already know that I’m willing to participate in the conversation when questions are asked of me; but the point here is to bring the other person up to my level of talkativeness if at all possible (because, as described under the Situational Awareness header, not everyone is willing to talk to you, and that’s fine).
1. Act like old friends
Confidence is key in conversations with people you don’t know. A big smile with warmth in your voice will take you a very long way.
How do you greet old friends you haven’t seen in forever? You might hug them, but aside from that, you’re going to ask tons of questions all about their life because you know it’s been a while since you caught up.
By initiating a new conversation / new relationship with this approach, you’re going to set the other person at ease that you are someone it is safe to talk to. You don’t feel like a stranger, but you feel more like an old buddy they’ve just lost contact with.
What are other techniques to practically pulling off this step? Refer to the next one.
2. Actively engage with eye contact, body language
This one’s more difficult for some people than others (I wholeheartedly admit that I struggle to maintain eye contact with most people for more than a few moments), but if you can find a way to work this into your behaviour, it’s got the potential to pay dividends in building rapport in an accelerated amount of time.
Demonstrate to someone that you’re interested in what they have to say by looking them in the face when they are talking. Do not be on your phone or checking the notifications on your Apple Watch (personal pet peeve). Indicate with your body that you’re also actively listening for what they’re saying.
No one likes talking to someone they think is only half-listening. It’s that simple.
3. Ask about the situation you’re presently sharing
At this exact moment in time, you two happen to be in the same place. What led you here? Are your friends getting married? Are they also renewing their license at ServiceOntario? Are they always walking their dog on the same trail?
Just by being in the same place at the same moment, you are sharing something. Start with that. Ask questions about how they ended up here. Don’t assume they got here the same way you did. Be polite yet curious.
4. Get comfortable with “awkward” silence
I have absolutely never been a fan of someone declaring “…well, this is awkward” if they’re not doing it in a joking way.
Things do not become awkward on their own. They only become awkward if we allow them to become awkward.
What this means is that a very real part of “awkward” silences is just mind over matter. If you consciously decide for yourself, “Not talking is totally permissible,” then you have no fear of the awkward silence. I mean, then it’s not awkward at all: it’s just silence.
On the topic of awkward silences (or perceived awkward silences): what do we know to be true? Well, it’s probably fair to say that most people are not comfortable with them at all. What this means is that, if we are the ones comfortable with awkward silence in a conversation, the other person is likely going to start rambling to fill it.
One of the best ways to get someone else talking is to learn how to stay silent long enough for them to have the space to. You might have a comment or follow-up question ready to go in your head, but hold onto it just a little longer and you might find the other person in the conversation finds something new to talk about because they feel uncomfortable being quiet.
5. The Netflix fallback
If you’ve exhausted the technique in Step #3, this is my absolute #1 go-to question for generating conversation.
Everyone has a completely unique taste in movies and tv shows. Ask about theirs. It reveals a lot about them as a person if you’re reading between the lines.
No matter how they answer this question, it’s easy to follow up on:
Do they mention a show you’ve heard about? Ask them if it’s lived up to the hype.
Do they mention a movie you’ve never even heard of? Ask them what drew them to it.
Do they mention a movie you love? Fantastic! So much in common. Share about your favourite part and ask for theirs.
Do they mention a show you hated? Air your grievances and see why they don’t (or do) share them.
Do they tell you they don’t watch Netflix? Do they read? Listen to music? How do they spend their off time? Ask more about that.
Again, no matter what they give you, you’ve got something to go on.
6. Sophisticated versions of toddlers asking “Why?”
If you haven’t caught on by now, my technique is just a more sophisticated version of toddlers that ask “Why?” over and over when they’re learning about the world.
For even more points, cover the entire 5 W’s and 1 H: Who, What, When, Where, Why, and How.
If the only thing you’ve noticed is that they’re eating a Roast Beef Sandwich on Rye bread, ask them about it. Did they put mayo on it? You’ve never really been a mayo person. Mustard though! And perhaps they also love mustard, but primarily on Turkey. Boom. Now you’re rolling. You might only be talking about sandwiches, but it’s a start. (“How did you find yourself in a mall foodcourt alone eating a roast beef on rye on a Tuesday at 3pm?”)
7. Be direct and ask something unusual
The more conversations you have with complete strangers, the more you might feel like you’re having the same conversation over and over. That’s ok: it’s normal.
The more you ask questions, also, the better you might get at coming up with unique ones. Particularly if you have an acute attention to detail (or develop one as a result of talking to strangers frequently).
When those unique, unusual, direct questions pop into your head: ask them! People might initially be a little surprised by the question, but if you’re engaging with the right person, you might be surprised to get a proper response.
Note that this technique is not advisable for the novice conversationalist. You’ll want to have confidence you can steer a conversation in a totally different direction in case you’ve touched on something pertaining to childhood trauma… or adulthood trauma… basically just trauma of any kind.
I’ve found myself in conversations with the President of the company I work for, and I’ve asked her what her greatest weakness is as a leader. I was impressed when she answered me candidly. She could’ve easily politely declined, but it led us to a new place in our working relationship to hear her answer.
You’ve gotta know your audience on these things, but once in a while: take a stab in the dark. You might be surprised.
8. Share an inside joke or make a fool of yourself
If you’re a naturally funny person, it’s probably super easy to crack a joke about something. But, even if you’re not naturally funny and are just dorky or punny (like me), that might be enough.
Most people are funnier than they think, but not in the traditional sense. They probably don’t think about themselves as particularly funny. This means that when you tell a dumb dad-joke that is good for little more than an eye-roll, they will feel disarmed and more like you are an equal.
We don’t tend to make a fool of ourselves in front of new people that we’re subconsciously trying to impress; so if you can swallow your pride a little and make yourself the butt of a joke, I’ve found that people are going to like that.
This is another surefire way to make Step #1 happen. You’re proving that you’re not above them in intelligence or humour: you’re on a level playing field, like friends.
9. Weekender / Dream vacation
If the Netflix question didn’t pan out for you, this is another really great one to have tucked in the back of your mind:
How do you spend your weekends? Where would you go, and what would you do, on an all-inclusive vacation?
Show me your credit card statement and how you spend your spare time, and I’ll show you what actually matters most to you.
We spend our money and time on the things that we value, so uncovering these in a conversation is going to give us a much more intimate look at our conversation partner.
If they don’t have a dream vacation, ask about where they’ve been on vacation in the past. If they haven’t been anywhere, ask why they’re happy staying home.
If you just utilize Step #6, you’re bound to end up in a conversation that takes you somewhere.
10. Get them to teach you something
I have seen some of the most shy people I’ve met become chatterboxes because I asked them to teach me something.
This technique combines elements from many of the other steps, and I think that’s why it works so well (if you’re in an environment you can utilize it).
Asking someone to teach you something is a compliment: it’s saying that they are smarter than you, and you’re hoping they’ll share their knowledge with you. And, assuming you’re asking about something they at least kind of find interesting, they’re probably going to be happy to share.
This technique doesn’t level the playing field though: it actually tips it in their favour. It also helps get the conversation off of them as a person, and onto what they know, which can be really disarming for some people. Once you’ve got them chatting, it’s easier to steer the conversation where you want it to go (like into personal territory) because you’ve then built a bit of rapport with them already.
If you’re in a place where someone can teach you about something, you’re going to be off to the races in a conversation. You’ll be old friends in no time.
The 15% Guide
If the person you’re engaging with is a halfway decent person, they will likely ask you some questions in response. This is great! You don’t want the conversation to be completely one-sided.
When answering someone’s question, or interjecting a follow up comment of your own, I suggest adding an additional 15% to your answer than you were asked. You don’t want to be seen as rambling, but you create just a little more opportunity for continued conversation by sharing a little more than might be absolutely necessary.
Trying to have a conversation with a complete stranger is not an opportunity to be quiet and reserved. Give them a bit to work with in the same way you are hoping they’re going to give you a bit to work with.
In Summary
Having meaningful, engaging, easy conversations with complete strangers is nowhere near as hard as people believe it is. Most people just haven’t been taught the proper techniques of what they’re doing. It’s sort of just like grammar: you don’t always comprehend why you’re doing what you do, you’ve just rehearsed certain patterns through decades of repetition.
Hopefully by drawing your attention to some of my favourite ways to get people talking, you’ll be able to see how it’s not that difficult.
Many of these techniques can simply be memorized as tricks or go-to’s. They don’t involve solving someone like a mathematical equation.
Of course, these are all just my techniques from years of personal experience. What’s worked for me might not work for you if your personality is just nothing like mine (and you can’t fake it for a time being with someone you’re meeting).
Try these out and take note of what works. Remember new discoveries if you can. They’ll help you in the future.
This is the last thing I’ll say: having meaningful conversations with complete strangers is not as difficult or scary as you might’ve believed up until this point in your life. Take a deep breath, fake a little confidence, and ask questions.
You’re going to be surprised how easy this actually is.
