How to tell a funny story and really entertain people

Learn how to tell a funny story. By getting why and how stories resonate. Plus how to structure a good story to make people laugh.

How to tell a funny story and really entertain people

Just imagine being at a cool party, standing in a group of five people you just met. There is a small silence. That’s your cue! You start telling your funny story! “So I was….”.

As you animatedly tell about your adventure, ten ears are tuned to the sweet sound of your voice. The group is glued to the ground. You’ve peppered your story with a few foreboding hints. You see their mouths already twitching in the anticipation of laughter.

As you drop the punchline; “… so the bus driver said: “Sorry sir, no penguins onboard next time.””, everybody bursts into laughter. You feel the adrenaline rush through your veins. You get a high five and pat on the back, one guy is straight up crying from pleasure.

Man, it feels good to entertain!

The cute brunette next to you gives a coy smile while she steals a glance. You poorly even notice in the rush. The competitive bro in front of you is entertained, but wants to top your story, so he already buts in with his anecdote. That’s cool, let him try. You entertained the bunch, and you will do it again that evening, with a few more of your cool stories!

Sounds awesome right?

Let’s learn to tell a funny story!

0. The Love of Stories

We all love stories! It’s why I binged Westworld, I compulsively read One Piece every week and enjoy Marvel movies (though honestly, the story is basically the same every time).

It even helped me overcome the contempt I had for books. I just somehow started reading Game of Thrones 7 years ago and haven’t stopped reading since (yes, I finished the first book).

But even better is telling stories.

It always envied friends who could just entertain people. Just by telling some random compelling narrative.

Why couldn’t I entertain people like that? When I told a story, people politely listened, but pretty soon started looking away for some excuse to leave.

What about you?

So what’s your experience? Can you tell a funny story? Why not?What is the difference between you and that charismatic colleague? Does your social anxiety limit you to socialize? Or do you feel it’s hard as an introvert to connect?

Maybe your stories are too long, anticlimactic, or just not funny. Or do you tell them all scrambled up, going back and forth, mixing up the punch line?

As you mess up, you feel people pulling out, disconnecting from the conversation, focusing on something more entertaining. Your courage seeps out, you start sweating as you’re barely able to mumble the end of your story.

I’ve been there, … It hurts, I know.

Luckily, you can learn the art of telling a funny story.

Before you freak out and think “I don’t know any interesting anecdotes”, … calm down. Because you do! No worries, all people have interesting things happen in their lives. You’ll just need to recognize them and know how to form them into a story. It can often be the simplest quirky things in life that are the funniest.

Normally I always hammer on being interested in other people. But sometimes you’ll have to step up to the plate. Story time is the moment you hog the spotlight. That does mean being a bit vulnerable at times. But don’t worry, it is great for connecting to people!

1. The Power of Storytelling

1.1 Campfire Confessions

We are made for stories, it is a binding factor in our lives. It is the most effective way bring across your standpoints and adventures.

It is its evolutionary point, to transfer knowledge and experience, from one tribesman to another. That’s how we’ve been doing it for millenia.

I always like to imagine we used to huddle together around a big campfire, listening amazing stories. About grandma absolutely slaying one mammoth after another. Amazing!

Storytelling is so effective because of our amazing mind. It fills in gaps, it connects facts and extrapolates context out of experience. But even more amazing, we humans can imagine past and future events!

1.2 Our brains as simulator

It sounds ridiculous, but the ability to simulate in our head what happened or is about to happen, makes us unique (1) No other animal can do that to the extent we can.

Furthermore, we can understand concepts. Abstract elements like tribe names, brands, nation states. These are not real things, I mean, what is “Tesla”?

It in itself, Tesla is nothing. But in our head we can make an idea of the company, culture, philosophies, people and economy that somehow work together. Because we all name it Tesla, the concept kinda becomes real. But even if we replace all its employees, factories, and by god, put someone else in charge than Musky, we would still have Tesla (2).

Furthermore, we use stories as analogies all the time. The Bible, Kuran and the Vedas, and every other holy book,… but for that matter also Harry Potter and Lord of the Rings are filled with stories, that didn’t necessarily happen.

I know, I know – blasphemy, I wish Hermione was real too.

Yet these stories are meant to teach us very real lessons. Jesus was all about them forgiveness, Buddha taught to let go of desires, Potter about overcoming the fear of death. You don’t have to be religious, or a fantasy nerd, to appreciate the lessons being told.

1.3 Epic Formula

Within most stories there are typical structures. These speak to our deepest instinct. The most important one Joseph Campbell revealed in his “Hero with a thousand faces”. Were he explains that every epic, from Star Wars to the adventures of young Gilgamesh, follows this path.

Modern series writers use this as well. Dan Harmon & Justin Roiland use a slimmed down model for making their 20 minute Rick and Morty shorts. They let different characters step in at different moments in this cycle, but still make them complete the cycle. This way we can experience compelling stories in a few minutes that resonate with our deeper story instinct.

This structure is unconsciously recognized by everybody in every culture. Because it speaks to a fundamental truth of development as a human. Even though, the style can differ widely.

2. The Anecdotes

So that’s the bigger picture, back to daily life again.

We are not going to narrate an epic poem at the water cooler every day. No matter how well it resonates with all people on earth. It misses some, …. practicality.

Nope, you want to know how to tell a funny story. Just something to entertain people. So they will find us interesting, or better yet, funny! You’ll help them fill that small existential void of awkward silence.

Just by telling a funny anecdote.

An anecdote can be about something you experienced, something you heard or maybe a bit of fantasy. A good story doesn’t have to be true. See it as telling a short story like a comedian.

That can mean exaggerating and stretching facts a bit. Sometimes you just come up with a bullshit story. Most people will know you playfully alter the facts, they won’t mind. But more often than not, just stating the truth, and emphasizing how weird it is, will get you most laughs.

For example, there is a geeky programmer in my friend group. He doesn’t seem to have an exciting life. He isn’t an extrovert and doesn’t tell a lot of stories. But when he does, ow boy, he brings out the big guns.

He occasionally surprises us with his rare epics called; Martin’s sexual confessions. In it he takes us on a 4-minute adventure, telling about what crazy (but sexy) adventure he experienced. The stories are amazingly funny! He has only told us four crazy stories over the course of five years. But I just can’t wait until the new installment.

A nice example of how quality beats quantity. None of us care if the anecdotes are real or not. They are fun, that counts! Besides, it shows how being an introverted geek does not mean people can be absolutely absorbed in your adventures.

3. Structure of your funny story

Back to telling a funny story. Just like the epic, the funny story has a typical structure and elements as well. All recognized and important for it to be compelling.

The elements are anchor point to lay out the context and build tension. The build up of tension is important. Because it is the release of this tension that creates laughter. This is done by flipping expectations at the end of the story. How the surprising twist is presented is the humor.

So as well a strong build up, as a good twist are important. How do you structure this? A funny story consists of:

1. The setup
2. Pattern
3. Foreshadowing
4. Characters
5. The Twist

Let’s take a look:

3.1 The Setup

This creates the context. It needs to be as short as possible, but recognizable. You sketch out a setting everybody will understand. So things like:

“So I was driving home, …”

“I brought my kid to the doctor, …”

This little sentence or two, should be ample to explain where or when the story took place. You can only skip where and when if it is not relevant to the story. You don’t have to be exact about it, “one summer”, is better, than “July 2012”

3.2 Pattern

You explain about a routine, a habit or pattern that will be broken in the story. Sometimes this can be implicit, but most of the time you need to sketch it out:

“Normally my commute is pretty fast.”

“My regular doctor is a pretty attractive, but very formal, woman.”

This second element already builds some tension, your audience has some context. What next?

3.3 Foreshadowing

This is you alluding to something that is about to happen. You already hint at a future twist, just lifting the tip of the curtain. This is to build more tension in your story.

“But his was no regular drive”

“Well today I finally impressed the cute doctor”

3.4 Characters

Often, besides you, there are more characters in the story. If people don’t know you well, sketch out your relevant characteristic and mood. Do the same for other actors in the story. Just the important stuff, people will fill in the blanks

“Well this officer was having a bad day”

“I’m a bit flirty, but my doctor is very professional”

3.5 The Twist

When the tension peaks, you drop the twist. Hit them with the punchline. You tell the unexpected turn of events. Something that flips the script. Something people didn’t see coming. No twist, no funny story, then it just a logreport. If done well, this is where you and your audience erupt in laughter

“Well I got home earlier alright, just in the back of the police car”

“And just when the cute doctor started flirting back, my kid pukes all over me!”

3.6 A Small Recap

In your story you build tension, you sketch out a context and introduce the characters. With that you establish a pattern that comes under more and more pressure. By using foreshadowing, style and the established structure you build tension. When the tension peaks, you drop the twist. The script is flipped, the pattern broken and the tension is released! This release is what causes people to laugh!

Example Story

On my flight back from holiday last month [setting], I was sitting next to a baby [character]. We all know how much noise babies make on a flight [pattern]. So I dreaded not sleeping [foreshadowing] because of a 100 dB sack of piss and shit sitting next to me! So yes, as expected, I didn’t close my eyes at all in a 6-hour flight. But not because of the noise, I was just all tensed up in anticipation of the kid crying. [Twist] The baby never let out a squeal

4. Features of a Good Story

So we got the structure laid out. Now lets talk about important features of good stories.

First of all, a story should be short and sweet. About five minutes max. You’ll lose your audience otherwise, no matter how good a storyteller you are. Don’t ramble on about related facts and side stories. Stick to the story, use the structure and don’t add too much. You can always tell another story afterwards

Furthermore, a story should be relatable. People mainly think about themselves, your story should be able to happen in their life as well. Or at least close enough that they can imagine the scenario.

Parents can relate to problems with kids, colleagues can imagine office politics, and classmates know about weird social pressures. Use the right story for the right audience.

For humor to fit, you should never see yourself as less than your audience. There is this whole status thing related to humor. View yourself of equal status to your audience. Don’t see yourself away as any less. Self deprecating humor can work for a while, but it’s not a sustainable strategy.

4.1 A little more from your side

Telling an embarrassing story does mean being vulnerable. This is hard, but a great way to connect to your audience. Even the normally unspoken mundanes of embarrassment is funny in itself!

People bond over quirky stuff, because we all have weirdness in life. Talk about something stupid you did, or about a weird habit you have. We all have them, it makes the story more relatable. Exactly because of your openness, you invite others to open up as well. Giving and gaining trust

If I tell a story about finally talking to my crush, only to be pointed out by her that my fly was open. I tell something embarrassing. But also something people relate to. Everybody makes blunders, I just flaunt mine while laughing about it myself. You’ll get laughs and sympathy in return.

Before you start sharing everything, there are some topics to avoid. First of all skip boring subjects, like talking about food or television. Also, skip medical stories. Most people don’t care, or are just bummed out.

5. Style and the power of using your voice when you tell a funny story

Make sure, that if you tell a story, you are heard! No mumbling, but articulating. Talk from your belly, not your upper throat, so your voice is strong and carried. It is important that people pay attention, signal that by the strength of your voice

Furthermore, you can use the vast spectrum of your voice and way of telling, to color your story. Find your style, and don’t be embarrassed to practice in front of mirror or spouse.

You use your voice as well to create the tension in your story. By playing with speed, volume and pitch. You can get people on the edge of their seats.

I wish I could give you just 5 pointers, but you have to figure this out by yourself. Find your style! Learn how you tell a funny story. For some people dry monotonous syllable spewing works best. For others rattling of high-pitched squeaks is the best way to induce laughter.

5.1 Emulate and practice

Unsure, how to style your story telling? Emulate people you love listening to. Take a look at your favorite comedian or speaker. Open Netflix now, open up a comedy special – laugh and learn.

In the safe confines of your room, practice emulating some styles and see what fits you best. How do your examples play with volume, pitch, timber and speed? In what way do they build up to a twist in the story? How can you apply elements of their style? Not necessarily the text, but all embedded signaling by voice and body. Don’t try to imitate, but create your own style out of what you learn.

This is not a one-day process, but something you embed in your story telling over the long term. Some of my favorite comedians I learn from are: Dave Chapelle, Hans Teeuwen and Jim Jeffries.

5.2 Beyond your Voice

Furthermore, when telling your story, embed an energetic upbeat vibe. Nobody wants to listen to a downer. Even though you may feel anxious, work up positive energy nonetheless.

How? Do what you love to get into a good mood in advance. Work out, read a book, pet your dogs, whatever gets that smile painted across your face. So if you go meet people, you come bringing good vibrations.

As you tell your funny story and you hit the punch line. There are two ways to go about it; either laugh authentically about the joke you just made :)! Display confidently how funny you thought it was. Or don’t laugh at all, and let your audience release their tension by filling the silence with their laughter. Both strategies can work – find out what fits your style best.

But don’t chuckle halfheartedly, that somehow signals you are not sure if your story was funny. Personally, I go for the full hard laugh afterwards, while having a foreshadowing smirk on my face all way through the narrative. But if you have a dryer way of storytelling, the silence will work wonders for you.

Lastly my friends, eye contact. If you can integrate all the above, I’m sure you can look the friendly party people in the eyes! It is very important you do, not only for story telling, but in all communication.

So much is told by facial expressions. It communicates interest, anticipation, boredom, anxiety, enjoyment, or any other subtle emotion we experience. As you master storytelling, you’ll even be able to adjust your style, according to the cues you get.

To be continued

Time to tell a funny story

Alright, let’s just gather our wits for second.

That was a lot of theory, and of course not all implemented at once. But you could start by constructing 3 stories to tell next time. Think of weird things you have experienced or noticed in your life.

Think about events that went against the grain. Then try to fit them in to the structure we discussed: Set-up, pattern, Foreshadowing, Characters and Twist.

Does your story work this way? Need a little tweaking? Practice telling your story to a friend. How does your style work? Need some more practice? No problem, practice more. But don’t hesitate to start trying in the wild.

Go entertain that dude at the copier, your cute classmate in the college benches, or those stranger (soon to be buddies) at the bar.

Make me laugh ;)

Let me know how it goes. Love to hear you feedback, but even more, one of your stories! Tell your funny story (or any question) to and I’ll be sure to send a cool anecdote back :)!