Part 2: How to Have a Great Conversation With a Stranger

Talking to a stranger feels a lot like this...

Talking to a stranger feels a lot like this...

How do you talk to a stranger? Not easily. But, like most difficult and slightly risky things in life, this can be a really rewarding experience. It’s way more difficult than talking to someone at happy hour or structured networking event who might be a stranger but is at least attending a function that expects people to talk to each other (see Part 1 in our series to master this scenario).

Nothing in inter-personal communication is harder that talking to a complete stranger at a café, bar, or book store. Nothing.

So how do we do it? First, let’s figure out why people want talk to a stranger. Here are some common and real-life reasons people give:

“I want to improve my networking skills…” / “Overcome social shyness and gain confidence...,” / “Beat my fears…,” / “Be a more interesting person…,” / “I want to learn from people…,” / “I’m new to the area and want to make friends...”

Who doesn't want to have this guy's reputation?

Who doesn't want to have this guy's reputation?

If this idea of walking up and talking to some complete stranger scares you, don’t fret. Most people suffer from some form of anthropophobia or interpersonal relation/social phobia. It’s natural. In fact, there are entire subreddits on this fear and even help groups to overcome it. Quora has dozens of questions with hundreds of answers on how to master these skills. You can find a number of Ted Talks on this too. What we're trying to is that you (and I) are not alone.

Even though this is a difficult skill (and despite the psychological hurdles involved), there are plenty of reasons we’d like to master this seemingly dark art or Jedi mind trick.  Who doesn’t want to sidle up to some stranger at a coffeeshop, spark some life-altering conversation, have the whole room crowded around to hear every word, and then walk out as the World’s Most Interesting Man/Woman?

Here’s how to do it with six steps.

For starters, especially in America, people are generally skeptical of a stranger approaching them to chat. We have conditioned ourselves to assume someone crazy enough to just walk up and talk to us out of the blue must up to something: selling something, trying to pick us up, swindle us out of cash. We don’t know what, exactly…but we assume this crazy person is up to something. So Step 1 is defusing this concern from the other person’s perspective.

Step 1. Defuse the Creepiness

There is a lot of bad advice in this department from friends and the internet. There’s no subtle or magic opening line that will win someone over and make them drop whatever they’re doing to hang on your every word. It doesn’t matter if you’re smiling more than normal or make the exact right kind of eye contact (common bad advice).

Defusing the situation is the key.

Defusing the situation is the key.

You see, what we’re trying to do initially is just find a person who is BOTH: a) willing to talk to a stranger, and b) has time available at that moment. This is no easy task.

We have to find someone who meets both criteria. This is why some seemingly amazing opening line doesn’t matter; if the other person doesn’t have the time available or simply doesn’t want to meet with a stranger, you won’t be able to lure them into a conversation with even the most interesting of one-liners.

This is why we need to take another approach: honesty.

Sound crazy? It shouldn’t. We’re simply going to tell this stranger that we’d like to talk and make sure they have the time available.

Here is the appropriate intro (note that this is NOT some underhanded one-liner…just the truth):

“I’m sorry to bother you and I know this sounds crazy, but I was just looking for someone to chat with. I’m not selling anything/hitting on you…promise. Would I be intruding?”

You’ve now helped both yourself and your new potential conversation partner because there’s nothing awkward or creative that they need to do to shoot you down. On the contrary, the person has an easy excuse to shoot you down without seeming like a jerk OR they accept your offer.

So, if they don’t have time, this is when you bow out gracefully: “I totally understand. Sorry to bother you.” And you move on.


Your new acquaintance offers you a seat…breath a small sigh of relief and proceed to Step 2.

Step 2. Use Your Best Weapon

Good news! You’ve made it past the hardest part (the initial contact). BUT…you’re not out of the woods yet.

At this point, the responsibility for what comes next is on you. This person is listening very, very carefully at what comes out of your mouth next. They want to figure out if they made a mistake or not in letting you sit down. Your next comment should play off your first one to both: a) reassure this person you REALLY aren’t there to sell them anything, and b) that this type of experience is something you enjoy doing.

Here’s a good follow-up line: “I appreciate it. I know this type of thing can be off-putting to some. In fact, it’s not easy for me either. Personally, I’m trying to [insert the honest reason you want to talk to strangers here…’get better at talking to people/overcome my introversion/learn about other people/build up my confidence/hear interesting stories/step outside my comfort zone.’]

As you can see, the possibilities are endless…as long as you’re honest.

If you can’t - or just don’t want - to memorize something like this, that’s no sweat: just stick to the truth. You don’t need to have some masterful delivery, you just need to put the other person at ease. The truth usually does that.

Humans are extremely good at detecting insincerity. Some are better than others, but unless you’re skilled at deceiving people, people will sniff out your motives right away, so let’s stick to the truth and keep our new acquaintance disarmed and interested in hearing more.

At this point, we’re on our way to an interesting experience. How many people can say they’ve ever made it this far? Statistically, not many. This is hard stuff (some people have literally worn a giraffe costume to get to this point). So let’s go to Step 3 and see how to move the conversation forward.

Step 3. Get Ready to Carry This Thing

Since we initiated the conversation, we need to carry it forward.

Since we initiated the conversation, we need to carry it forward.

Step 3 is a two-part process. We need to introduce ourselves and let our new acquaintance/friend share a bit about themselves.

When you introduce yourself, it’s best to give your first and last name (this shows you’re not hiding anything…yet another way to disarm your friend) and share what you do in life (where you work or study, for instance). 

After introducing yourself, pause to let your new acquaintance introduce him or herself. If they don’t offer anything else beyond their name, and assuming you shared something about yourself like what you do, then you should feel free to ask them the same or another similar question. “Nice to meet you John. What do you do for a living/How do you find this town?”

Easy. You’ve now successfully established communication with this person and the rest is smooth sailing. It might not feel like it at first, but what comes next is something very few people ever experience. So let’s expand beyond introductions in Step 4.

Step 4. Expanding the Conversation

We need to hear what our new acquaintance has to say.

We need to hear what our new acquaintance has to say.

This is the point in the conversation where you let your acquaintance speak about what’s on his or her mind. There’s a direct correlation between talking about ourselves and positive well-being (see our article on this here).

What does this mean for us and our conversation? If you want the other person to feel like they’re having a good and interesting conversation with you, let them talk about themselves. Ask questions that allow them to talk about who they are, their family, how they got to this point in life, or where they’re going.

If there’s a break in the conversation, which scares some of us, then use it to return to exactly WHY you wanted to talk to this stranger. Most people find this interesting because (as we all know at this point) talking to a stranger is hard and not everyone can do it.

We need to share our personal reason for wanting to talk to this person; this is not necessarily a one-size-fits-all. Do you find people’s stories interesting? Are you trying to learn from other people’s experiences? Are you looking for advice on some challenge most people face? Are you just trying to overcome your fears?

No matter your reason for wanting to have this interaction, go ahead and share this again and use it to ask more questions of your friend.

For instance, I like hearing about other people’s lives and how they got to where they are today. I’ll often ask how they ended up living in a particular part of the world or working where they do. I ask because I genuinely want to know the answers and the responses are usually exactly what I’m looking for. In return, I’ll share the same about myself. Either way, we’re both sharing and opening up all kinds of other avenues for discussion.

At this point, there are a lot of ways to take a conversation, but you’re not really talking to a stranger any more, are you? It’s much easier now. You can be more natural and engaging the way you would with your friends or people you know at work. Let yourself do this and don’t sweat any of extraneous factors people often talk about like eye contact, facial expressions, mimicking body posture. Just be sincere and interested in your new friend.

As with all good things, the conversation must eventually come to an end…in Step 5.

Step 5. All Good Things Must End

Ending a conversation, particularly an interesting one, can be hard to time perfectly. There’s no ideal time and you’re always walking the fine line between ending this at what seems like a lull in the conversation or powering through to another interesting topic. Either way, nobody does this really well, so don’t worry and again, try to be sincere.

Ending with something like this is best: “Well, I really appreciate you letting me sit down and chat. It was really interesting. I’m going to Have a good one.”

Step 6. Do a Mental Victory Dance did something most others never will. did something most others never will.

Congrats, you just accomplished what most people will never be able to do. Was it hard, yes? Was it worth it? That’s up to you, but most people find it rewarding. You’re on your way to becoming the Most Interesting Man/Woman in Your City…

The truth is that there are plenty of benefits from talking to other people. Statistically, this type of social interaction is great for your mental health, physical well-being, and helps you live longer.

The problem is that nobody wears a sign that tells you it’s okay and safe to walk up and talk to them. At Convers8, we want everyone to be able to have more of these spontaneous and interesting conversations with people all around us. We created Convers8, an app, for this very reason.

If you’re like us or you just want a more interesting experience in life, try out the Convers8 app and have a conversation today.