How to Appear Interesting in Conversations
So if you’re ever frequently around other people in conversations and you want to appear to be interesting or charming or have people walk away saying, “Hey, that person really was fun to talk to or had a great conversation,” here are a few things you can do to really stand out from others. Also, the opposite of that—how you could be boring and maybe you want to be boring or maybe you don’t—how to avoid it. The most important thing is to remember what people want to accomplish in a conversation.

People Want to Be Heard
Most people want to talk about themselves and be heard. How many times have you heard in relationship advice or counseling or therapy where people say, “I just want to be heard. I want people to listen to me”? That’s a key element of people’s needs as a human.

How to Make a Good Impression
So what can you do in a conversation? Well, you can try to not just listen but draw that out of them. Here’s a very specific thing you can say to a person if you really want to make a good impression. Obviously, the context has to be correct, but you can say:

“Look, think of a subject that you love to talk about, a story you love to tell, a topic that you love to talk about, a fact that you love to explain to other people—something that is unique to you that you just love to say out loud but that you don’t have people that like to listen to it. Maybe it’s a story you’ve told about, you know, when you were in college. You love to tell this story, but nobody wants to listen because all your friends have heard it a million times and they’re like, ‘Oh gee, he’s telling that story again.’ Maybe it’s something you know about because of your career, your job, your education—that you know about this very specific fact that nobody likes to hear because it’s boring. Maybe it’s a particular event that happened at your work, at your job, that to you is important, but to nobody else, they really care about it.”

Encouraging Others to Share Their Stories
Think of that in your head and give the person time to think about it, and say:

“Now I want you to tell your story, and I want you to tell it in a way that nobody else wants to listen to or that nobody else likes to hear. Just tell it from your own internal point of view without thinking about what I am reacting to it. Just say it however you want to say it. Don’t try to change it to make it seem like you think I’m going to like it more. Ready? Go.”

Now, you can change the wording, you can change the way you say that based on the context. Obviously, you don’t want to walk up to a stranger and say that. Or if it’s somebody you know a little bit but not too well, you don’t want to, you know, kind of freak them out by being too personal. But either way, try to beg a story out of them.

The Work Is Done Once They Start Talking
The good news is that’s all the work you’re going to have to do—thinking of how to say that. Once you’ve said that to the person and convinced them to tell their story, believe me, the work is done. They will then just go on—it’s like winding up a toy and letting it go.

Now, during that story, you have to be relatively genuinely engaged. You can’t just space out and look around or play with your phone. You have to pay attention to them, maybe occasionally ask a question or acknowledge, “Yeah, that makes sense” or “Gee, that was interesting,” and let them go.

The Key to Making a Good Impression
Now, is this going to be difficult to do? Well, it depends on your personality. You might not like it because you want to talk about yourself. You might want to tell your story and have somebody listen to it because you’re craving that kind of attention. Do that at a later date. If you want to make a good impression on another person, you will do that better by letting them tell you some unique or unusual or boring story to you rather than you trying to tell some story you think is exciting about your life to them.

Because that exciting thing about your life may not be that exciting to somebody else. It might be boring to them.

The Power of Asking Questions
And they’re not going to want to hear it. You’re not going to impress somebody with an exciting story about yourself in most cases—especially if you do that first. If you listen to the other person, or if there are four people in a room, ask them their stories. If there’s more than one person, you can even take this a step further.

You can ask one person to tell their story, and as they wrap up, say, “Great, that was interesting. Sally, what about you? What story do you have?” And then, if you’re the one who’s taking control of asking these questions, you can be like the Master of Ceremonies—the main character in the room. And I can guarantee you that it will have a big effect on how people walk away two or three days later, thinking, “Man, we were at that party, and you know, John was really interesting. He really carried that conversation.”

Making a Lasting Impression
They might even say that you said some interesting things—even if you never told your story—because to them, you were the one who orchestrated the whole thing. This can work in a business environment, a social environment, even if you’re dating. You can ask the other person the same thing.

Now, you don’t want to be fake in terms of your interest. If the subject that they’re talking about is really not that exciting to you, that’s okay. But what should be exciting is the fact that that person is telling you something—they’re sharing something about themselves. So you can be excited about the event, even if you’re not excited about the subject.

If You Want to Be Boring, Talk About Yourself
On the opposite side, if you want to be boring, go to a bunch of people and just tell a story about yourself. Because I can tell you that the story you have about yourself in your head—the experience and the vision of that time you went hiking in the mountains and found this lake and caught a big trout—you’re imagining it. To you, that’s an exciting story because you were there, you’re reliving it. But to the other people, they’re not seeing that movie in their head the way you are.

Customizing the Approach
And if it’s business, you might even want to prime the pump a little bit. So if you know something about that person—if you know that they were, say, the CEO of a stock company—you might want to say, “Well, how does this work in the stock trading industry? What is a story that you love to tell people about that is boring to a lot of people outside the industry?”