How to Tell an Entertaining Story

I remember the night I realized that I was a really, really bad storyteller …

I was in grad school, hanging out with grad school friends. A fraternity brother of mine, Rich, had come down to San Diego to visit, and we were sharing our college stories, most of which revolved around the dumb things we did while 1) drunk, and 2) being in a fraternity.*

Okay, so maybe 1) and 2) are somewhat redundant.

Anyway, I decided to tell everyone about my 22nd birthday, which Rich played an active role in, and which is a pretty funny story.

Well, it was a pretty funny story, until I chose to tell it this way:

I was out with a bunch of guys from the house, and I bought everyone a round of shots. But they refused, and I ended up doing all of them myself.

So I do eight shots in a span of about two minutes. Next thing I know, I’m sitting outside on the curb, and some random girl comes up to talk to me. I tell her it’s my birthday, and she laughs at me and walks away.

A few days later, I ask Rich about the incident, and I’m like, “Where were you guys?” And Rich is all, “You were leaning against my leg.”

I finished my story, and … dead silence. I was hoping for a few chuckles, but everyone just stared back at me. The moment was agonizing.

And then it dawned on me. No one was responding because they were all waiting for me to finish the story. They had no clue that I’d already finished it.

That’s how badly I tanked it.

As I stood there in morbid humility, Rich jumped in and saved my ass. He burst into laughter. It was the fakest, most manufactured laugh, but its intent was clear. He was communicating that the story was in fact funny, and everyone should in fact laugh.

I appreciated the help. I needed the help.

Over the next few years, that trainwreck of an anecdote smacked me every time I was in a group setting and thinking of saying something. So I vowed to learn how to tell anecdotes and stories in a way that would elicit laughter. Sincere laughter.

This is what I eventually came up with for my 22nd:

My 21st birthday, I was totally fine. I walked home on my own accord and never even puked. My 22nd birthday, though? That ended a bit differently …

A bunch of guys from the fraternity take me out and start buying me drinks. Well, I feel bad because everyone had already done that the year before, so I decide to buy a round of shots.

Unfortunately, every single guy refuses to take their shot. They’re all, “It’s your birthday. You’re doing the shots.”

And so, I do. In a span of about two minutes, I end up taking eight shots. You can probably guess where this is going at this point.

Now, I do remember downing the shots and telling everyone that I want to go to another bar. After that, everything goes blank. One moment, I’m inside Maloney’s, and the next moment, I’m sitting on the curb outside in the parking lot, by myself.

So I’m all alone, wondering where the hell everyone went. And then some random girl comes up to me. She’s super-nice and asks me if I’m okay. I tell her, “I’m fine. It’s my birthday, and we’re gonna go to Westwood Brewery. I’m just waiting for my bro Rich to come back, so we can go.”

And with that, she laughs, wishes me a happy birthday, and walks off.

From that point on, I have only sporadic flashes of memory from the rest of the night. So when I finally wake up the next afternoon, I try to piece everything back together.

I find Rich, and I ask him about the night before. I say to him, “Hey, so I remember at one point, I was sitting outside on the curb in the parking lot, all by myself, and this random girl came up and talked to me. I think she was worried that I was drunk and you guys had ditched me. So where the f–k were you guys?”

Rich looks right back at me, shakes his head, and says, “Yeah, that whole time you were alone outside, talking to that girl? I was standing right behind you, propping you up with my leg, because you were too drunk to even sit upright. That’s where I was.”

See, isn’t that better?

So let’s break this version down and see why it works:

First off, notice that it has a storyline. There’s the setup: I’m out for my 22nd birthday. I even throw in a bit of foreshadowing, hinting at how badly my night goes. Then I get to the main problem: I’m left by myself and have no idea where my buddies went. After that, I attempt to solve the problem: I find Rich and ask him what happened. And finally, I reach the resolution: Rich was there the whole time.

Aside from the story elements, I also use a comedy technique called misdirection. That’s where you lead the audience to expect one thing, and then surprise them with something else. In this case, I drop hints that my fraternity brothers are a-holes who don’t give a crap about me. This misdirection isn’t too hard to execute, since fraternity guys already have a reputation for being … well, a-holes who don’t give a crap. So as I’m telling this story, I’m expecting people to be thinking, “Well, this is typical frat boy behavior.”

And that ends up making the resolution unexpected and humorous — the fact that my buddies weren’t uncaring a-holes after all. I was just too drunk to notice my friend’s literal support.

(For you arcane types, notice that the story even has a super-objective — illustrating what a good friend Rich is. This is the exact type of story I’d want to share when introducing him to people he just met.)

So the next time you have a story you want to share, consider mapping out these steps. Tell a story that introduces a problem, builds suspense, and then offers a satisfying resolution — even better if the resolution is satisfying in an unexpected way.

To be clear, you don’t have to do this for every anecdote you share. In fact, if every single comment you ever make has a fully fleshed-out storyline, people may think you’re trying too hard.

At the same time, if you find yourself struggling to keep people’s attention in social settings, or even just speak up, learning to tell an entertaining story will only help you become more charismatic.

And that’s kind of the point of this site.

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