How to Make Memorable Small Talk (Even if You’re Shy)

You know that nervous feeling of not wanting to say the wrong thing when you first meet someone? Do you like weather? When they ask you a question, you give a simple, safe answer. And eventually, the conversation stalls out and neither of you knows what to say. If any of this sounds familiar, you are not alone. Because most of us suck at small talk. And it's for one simple reason. We started treating embarrassment like the worst thing that can happen in a conversation. But there's actually something that is much worse. Every time you ask the same tired question, you are limiting your chance to give the other person something to resonate with. And that can cost you more than an awkward interaction. It can cost you a potential friendship, a relationship, a job opportunity, a person that you might actually have wanted in your life. And that means that we can't just write off small talk as useless or stupid or something that only people with interesting backgrounds or funny stories can excel at. You have to start seeing it for what it is—a skill that you can and should develop. And I can promise you, from my experience teaching over 30,000 students inside Charisma University, it is actually possible to turn small talk into a life-changing connection. So in this video, I'm going to show you three modes of small talk that build on each other to turn conversations into meaningful relationships. And I'll show you exactly how to lower your filter so that you can become a more memorable conversationalist. Here's the thing. There is a good reason that we usually start small talk with the same basic questions. It's because we're all probing. Is this person normal? Are they someone I can actually click with? I like to think of it as a front porch to your house. You wouldn't just want to let anyone walk inside, right? And that is where safe questions and answers come from. Not because you're boring, but because you don't want to be turned away. So what gets you invited inside someone's home? Well, I can tell you what doesn't—basic, literal information exchange. That means trending news, the weather, local sports. By itself, this kind of conversation rarely creates connection. But here's what can actually work. For those of you who are introverted or shy, you can use the news as your launching point and pair it with fun or values. All that you have to do is take whatever news item pops up into your head or into the conversation and attach it to one of these two lanes. First, you've got news plus fun. Take a light, weird, or funny trending topic and throw it out there playfully. Like, did you see that story about her? Can you believe that people are actually—fill in the blank. Second, news plus values. Do the same thing but frame it as, did you hear about X? Honestly, it kind of pissed me off. Or it got me excited. Or I just saw X and it honestly made me realize. Using this framework will give the other person tons of threads to pull from and also allow you to find someone who shares your interests. That's your starting point. Once you're comfortable with this framework, you can actually drop news entirely and go straight into fun or values on their own. While news is literal information sharing, fun-based small talk is the exact opposite. If you want to give this a try, here's what you can do. When someone asks the same news-based questions, don't give the same predictable answer. Do the opposite instead. Give a playful, non-literal, non-serious answer that surprises them. This is exactly what my friend did at a party recently. There was a swanky event full of influencers and well-do's, and the first question everyone was asking was, what do you do? But instead of giving the expected literal answer, my friend confidently went up to a group and they asked. He said, oh, I'm homeless. And this immediately elicited laughs and created a playful atmosphere that was less stuck up and more enjoyable for everyone. Now, I know that you might not feel comfortable saying something like that, but the point isn't to say that I'm homeless like it's some magical line. It's that in a room full of people giving the expected boring answer, he did the opposite. He lowered his filter and said the first playful thing that came to mind instead of the expected thing that everyone else was reaching for. So now I will do the opposite. Now, this obviously has to be done selectively. You can't just say the opposite and expect to immediately be rewarded with a fun conversation every time. The skill is learning to recognize the right moments. So you want to start small. Try tiny inversions and see how people respond. Doing that will develop a sense for when to push a little further and when to play it straight. And if something doesn't land, smile, own it, and move on. I promise you the worst that happens is a little silence, and that is nothing compared to the laughs and the connections you get from actually trying. The one caveat is that if you rely solely on that fun mode forever, you will get a reputation as someone that is never to be taken seriously. So it's important to eventually pivot to what you really do care about. So if fun is about breaking the pattern and creating playful unpredictable energy, value is an earnest attempt to lead with what actually matters to you so that there's an opportunity for genuine real connections. Here's how you can do it. When you get to those typical small talk questions like, how do you know the host or what do you do? These are all opportunities to actually lead with what you truly care about. So instead of just saying, I work at a non-profit, you say, I love helping animals, so working at this place lets me do that. And honestly, I'm getting to live by the beach, and that's not such a bad perk either. Now, you've shared two things that you care about. You're talking about helping animals and being by the water. If you start to lace enough of these in, you'll stop wasting time on small talk with people that were never going to connect with you anyway and start finding ones that, like Velcro, match who you actually are. Did we just become best friends? Yep! So to recap, each mode matters. News gets you the basics of who someone is. Fun breaks the ice and builds rapport, and values opens the door to real lasting connection. But here's the thing. You lean into just fun or just values for too long, and you will come across as one note. To truly master small talk, you have to be willing to combine all three. And writing this actually made me think of a story that happened in a recent Charisma on Command team meeting. So we had this new team member, and he had been spotted up early on Slack. And somebody asked him if it was because he had a kid. Now, the normal answer that someone gives in this moment is, no, I don't have a kid. I'm just up early. But he took a social risk. He was a new team member, and so we were in the meeting, and he's asked, you know, why are you up so early? It's because he has a kid. And he says, well, actually, I do, but I'm just a deadbeat dad. And everybody laughed. And it took this very robotic beginning of the meeting that we had, and people started making jokes. And then somebody was quoting Daniel Day-Lewis like, I've abandoned my boy! I've abandoned my boy! And then we started talking about movies, and he's a big movie buff, and we actually were able to connect off of that one little joke to something much bigger. Now, he didn't map every step of that Smalltalk conversation out, but being willing to break protocol, to be playful, actually took us in the direction of values, because now he and I are working on scripts outside of Charisma on Command together, because I know that he's into movies. And to pull back the curtain a little on this, making this video has actually made me relive some of my own negative experience with Smalltalk and the connections that I let slip away by not doing this sort of thing. The most memorable example for me was when I was a fresh-faced college graduate. I'm working in Washington, D.C. I'm at a bar with my work friends, and my idol at the time, still someone I super admire, Tim Ferriss, author of The 4-Hour Workweek, took a seat in the same restaurant by himself. Literally, this is my hero in my restaurant. And I remember having the guts to leave my table, making the walk towards him, and then not being able to make him laugh or share what was important to me. And I walked away disappointed from that conversation. For years, I'm wondering what might have happened if I just said something different. But the good news is, because I worked on it, and I wound up building Charisma on Command around everything that I learned, I was eventually invited on Tim's podcast about 15 years later, and I got to tell him the story and get a good laugh in the process. And I didn't know what to do. I just said, you know, hey, Tim, Mr. Tim, I don't know. But what I want for you is to not have the same regrets in the podcast return that I had years ago. I want you to nail the first impression so that you don't spend those years wondering, what if the way that I did? I created Charisma University for that younger version of myself, the person who has the guts to make the walk, but not the skills to make that positive impression. If you've ever walked away from a conversation knowing that you had something worth saying, you couldn't find your way into it, that is exactly what the conversation module is built to fix. Now, the whole course is a step-by-step 30-day program that tells you exactly what to do each day so that you're radiating confidence and charisma naturally, not just when you're on, but as your default. And it comes with a 60-day money-back guarantee so there's no risk in trying it. Either way, I hope that you've enjoyed this video and I very much look forward to seeing you in the next one.