5 Tips for How to Tell a Great Story in Conversation

Dudefluencer: How to tell a great story in conversation

We’ve all been there: circled up with our friends outside as everyone shares stories to lighten the mood and build closer bonds. Your friends find ways to turn the most mundane events into something deeper, more meaningful, and entertaining. You watch in awe as you wonder when they learned how to tell a great story in conversation.

Then the circle comes to you; you’re put on the spot, unsure of what to say. So you try your best to little reaction. I get it, I’ve been there before. But I learned that being a good storyteller can be one of the most beneficial skills for being a more assertive communicator.

People tend to overlook that storytelling is an artform: good storytellers can connect moments of little significance into something more entertaining, while those who don’t know how to tell stories can bore you with the most incredible plot ever. That’s because the best storytellers understand these five tips for how to tell a great story in conversation and have practiced their craft for a long time. But you don’t need to be a professional actor or comedian to be a well-oiled narrator, you need to master a few tricks of the trade, and you’ll be the life of the party in no time flat.

The Importance of Storytelling

I never realized the importance of storytelling until graduating from college. When building close male friendships is difficult, and opposite-sex friendships are even more complicated. At a party post-graduation, I found myself sitting in the room’s corner, awkward and confused. I kept staring down at my soda, watching the bubbles pop and float. 

One of my friends pulled me into a circle of strangers, introduced me, and told them about a story I had written about my horrible fashion sense. Don’t worry, you can read all about that in my men’s fashion guide, but the critical part was as I re-told the all yellow-jumpsuit, or my grotesque pirate earring, I felt the room lighten up (at least for me). I was building connections through laughter and shared pain (who doesn’t have a terrible experience from middle school).

That’s when I understood the importance of storytelling in my own life. I never felt entirely comfortable in my skin, but it was a whole new Garrett once I started telling stories. The shyness went away, the performer in me that loves to show himself would come out. I’d entertain, make people laugh, but most importantly, I’d use those storytelling experiences to build deeper connections with my peers.

And that’s because storytelling is one of the most basic, fundamental forms of communication available to us. Uri Hasson and a team of researchers from Princeton tested out the way human brains react to storytelling. The researchers placed a woman in an MRI machine and asked her to recite an English and Russian story. Then, the study had many volunteers listen to the story while also getting their brains scanned. What happened next was incredible.

When the volunteers listened to the woman’s story, their brains engaged and synchronized. “When she had activity in her insula, an emotional brain region, the listeners did too. When her frontal cortex lit up, so did theirs. By simply telling a story, the woman could plant ideas, thoughts, and emotions into the listeners’ brains.” When we tell a good story, we are transferring our feelings, thoughts, and memories to them. We build connections and empathy. Learning how to tell a great story in conversation allows you to develop deeper relationships and gain new friendships.

Plus, stories are just more interesting than reciting data points or reading off a PowerPoint. Part of what makes Mike Birbiglia (Dudefluencer should just become a Birbiglia fan-site at this point) so talented is his ability to tell a story. Take, for example, this performance on This American Life, Birbiglia captures the audience’s attention with humor and a well-crafted narrative. We find ourselves throughout the story synchronizing ourselves with Birbiglia’s re-telling. The same goes for most stand-up comedians.

Lani Peterson writes in Harvard Business, “Scientists are discovering that chemicals like cortisol, dopamine, and oxytocin are released in the brain when we’re told a story…If we are trying to make a pointed stick, cortisol assists with our formulating memories. Dopamine, which helps regulate our emotional responses, keeps us engaged. When it comes to creating deeper connections with others, oxytocin is associated with empathy, an important element in the building, deepening, or maintaining good relationships.” The science behind storytelling makes a lot of sense: through world-building and strong narrative, we unlock certain aspects of our listeners’ brains and encourage them to react in ways that build connection and empathy.

But to get those brain functions working, you need to tell a good story. And when learning how to tell a great story in conversation, these five tips should get you well on your way to becoming a stronger storyteller.

1. Have a story worth telling.

As a kid, I’d always rush home to tell my mom about something funny in school. And as I did my best to spit out my story without laughing, it was still the same reaction: silence. Now that’s not because my mom didn’t have a sense of humor, or that I was a lousy storyteller, but so much of it is because I didn’t know what stories were worth telling.

You should ask yourself before telling a story is whether or not it’s a universal story or something that works only with a select group of people. For example, take a story about your fantasy football league and include a bunch of specific references and inside jokes that everyone in the league would get, but few else. Now imagine telling that story to your partner? Would they understand? The more you have to explain yourself, the more time you’re taking away from the narrative.

When I taught creative writing, the first thing I always told my students was to figure out what messages are universal before telling your story. If we look at the Harry Potter series, no one in the world has been to Hogwarts, practiced magic, or is a wizard. But J.K. Rowling is a millionaire because of her narrative; why?

Because she found the universal truths in her story: friendship, coming of age, the battle between good versus evil, everyone can relate to at least some of those themes, which is why Rowling is booming, and most authors aren’t.

If you want to know how to tell a great story in a conversation, think a bit about your narrative’s universality. Can strangers relate or empathize? If so, then you probably have the most crucial aspect of storytelling.

Remember, your experiences are unique unto yourself, but themes are universal, and life is full of them. I’m not suggesting taking the time to write out your story before you tell it, but think about whether it’s worth telling in the first place. 

2. Understand the structure of a story.

You have a story that you deem worthy enough of being told, now let’s go back to high school language arts to see what makes a great story versus a boring romp. Remember the plot charts?

I hate to say it, but your ELA teachers were onto something. Since the beginning of time, we’ve been telling stories, and geniuses like Kurt Vonnegut have managed to turn the structure of those stories into a science. In the clip below, watch as Vonnegut dissects some of history’s most remarkable stories in a way that’s understandable and entertaining.

Every story you tell should have a beginning, conflict, and resolution. It might make more sense to watch this brief story from Dwayne Johnson on Conan O’Brien. If you’re looking for good examples of live storytelling, watch interviews on late-night television as good hosts can extract information from their guests. In the case of Johnson, the story has a beginning, middle, and end. And of course, since Johnson is so charismatic, he plays his role as a storyteller to perfection.

So when you’re wondering how to tell a great story in conversation, make sure you take the time to figure out the structure of the story you’re telling. Build up to that ultimate funny moment, or leave your friends wondering what will happen next. Make sure you stick the ending though, that’s what everyone is going to remember.

3. Make your story engaging.

You’ve got your theme and plot, now what’s next when learning how to tell a great story in conversation? Here’s where your flair for the dramatic comes into play. You want to make your account not only well-thought-out but engaging as well. We are trying to get that dopamine and oxytocin flowing, and the best way to do it is through some engaging storytelling.

There’s a way to tell a story about going to the grocery store that can capture folks’ attention, but if you go step by step by step, you’ll start seeing a bunch of blank faces and dead eyes before you even reach checkout. An engaging story needs to think about the concrete details you can include throughout your re-telling. An easy way to remember is to think about how you can best use the five senses.

The more sensory images you place in your listener’s heads, the more likely you will synchronize brains. Here’s an example from John Mulaney. Mulaney’s bit is about a party he went to as a teenager, and what makes it hilarious and engaging is the imagery he chooses to share. Especially the section in which Mulaney utilizes Ratatouille to describe the kids at the party scurrying away like rats. Even if you haven’t seen the movie before, most people can imagine a group of rats running away. A simple metaphor does it’s job to perfection.

It’s always helpful if your story is interesting, to begin with. A story about a flight delay isn’t that fascinating, but the story of you ending up on the wrong plane and landing in another country probably is. If you’re looking for another example of an engaging storyteller, watch this clip of Will Smith shared a story about borrowing money for gas from a fan. 

4. Make people laugh.

I’ve come to find out that there’s no more terrific way to build connections via storytelling than through humor. I previously wrote about how to be funnier, so it might be useful to take a break from this article to check that one out before going further.

Now that we know everything, we need to know about being funny, why is it important to add humor to our storytelling? When we make jokes, there’s already a vulnerability level that we are sharing with our audience: we bank on them laughing at our comedy, but the silence could be horrifying. Add in the fact that our story might already be self-deprecating in some form or fashion; then, we’re extra vulnerable.

We’ve already learned from the importance of male friendship that vulnerability is essential in building close male friendships. And the same goes for telling a great story in conversation.

According to a study, “shared laughter may communicate to others that we have a similar worldview, which strengthens our relationships.” When we are telling stories, more often than not, we are trying to build a connection with a group of people (or just one person). Science says that laughter is one way to communicate and develop those relationships. Laughter is also just a generally good barometer of how well your story is going. Did you hit a big punch line to silence? Maybe it’s time to speed things up a bit. Or is everyone rolling on the floor laughing? Then you know you’re killing the storytelling game.

One of the easiest ways to add humor to your story is by acting it out. For example, this Donald Glover bit: one of the earliest laughs comes from his impression of a girlfriend. She probably doesn’t behave exactly like that, Glover overacts and adds a snide voice to get the crowd laughing. 

Think about your story for a moment: how can you act it out? Are there any funny characters? Maybe there are some actions you can exaggerate that will make your story more amusing. Anything you do to make your audience laugh will bring them closer together.

5. Art of timing

Mastering the art of timing is one of the most challenging skills to learn when studying how to tell a great story in conversation. For one thing, it requires you to read a room and interpret other people’s body language on the fly. Of course, that also means possibly changing your story as you tell it. Go too long; you’ll see your friends start drifting away. Cut it too short, and you’ll leave folks unsatisfied.

Timing and comedy go hand in hand, so it’s a no-brainer that I look to Jerry Seinfeld as one of the timing masters.

So how do we master timing?

Let’s look at timing from the angle of comedy. Greg Dean told The Cut, “the reason people say comedy timing is the most important thing, but nobody can talk about it in any useful way.” Dean proceeded to come up with two comedic timing principles that he teaches his students. The first, “[Dean] started analyzing audience laughter and found that a good, solid laugh usually comprises an initial burst, then a pause for breath, then a rise to a peak.” As for the other, “The second principle involves what’s called tagging your jokes, adding a quick verbal redirection after the punch line, once or even several times.” With all of these tips and tricks, though, for Dean, emphasis needs to be on the relationship you have with your audience.

The same goes for any storytelling you might be doing in conversation. The more often you tell a story, the easier it will be to pick up on the little things that could make it better.


When storytelling, the truth is that practice makes perfect. The more times you tell a story, the better it will become. And in no time, you’ll figure out how to tell a great story in conversation.

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