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  • Ben Stower

How to Write Dialogue that's Entertaining & Clever

Dialogue on the page is very different to the dialogue we hear and speak on the streets and in the homes and workplaces we inhabit. Generally, dialogue on the page is clean, witty, interesting and informative. More importantly, it is edited.

There are only a handful of writers who can write amazing stories without editing and none of them exist. But this series is called Writing Blind, not Editing Blind, so we’ll leave it at that.

Now, before we go any further, I must acknowledge that in writing, for every rule there is a way to break it well. There is also a way to break it horribly. But we must know the rules before we can know how to break them well. Otherwise we’re not breaking rules at all. In fact, we don’t know what the fuck we’re doing.

So, what are the key elements to any well-written dialogue? It should serve at least one of the following purposes:

  • Exposition

  • Humour

  • Characterisation

  • Advance the plot

  • Describe the scene/setting

Exceptional dialogue usually serves more than one of these. Of course, there are no doubt more purposes that dialogue can serve – and sub-purposes of these purposes (tumble, tumble down as far as we can go) – which we’ll discover as we practise. But these are the main five, or the Big 5 if we want to relate it to an African safari. Don’t ask me which one is the lion.

Cute kitten on a bed

No, that's not a lion, but goddamn if that kitty isn't cute.

I guess, if you’re looking at those five main purposes, you’re looking at the bricks and mortar of dialogue. But they’re no exactly what makes dialogue pretty or memorable. They’re a necessity, don’t get me wrong, but there’s something missing that gives our dialogue life or makes it that little bit more interesting for readers.

Really memorable or engaging dialogue should also:

  • Develop relationships between characters

  • Foreshadow events to come

  • Emphasize theme

  • Increase conflict

  • Give our characters distinct voices

Ultimately, dialogue is how we create three-dimensional, lifelike characters that leave the page and roam our readers’ imaginations. And as we get better at writing dialogue, we can use it to play with our readers’ perceptions, lulling them into false beliefs about characters or plots then spearing those preconceptions with a fucking zinger of a line.

God damn! I’m jazzed right up to 13 on all this dialoguing potential. Let’s skip this boring theory and get right to practising ... is what I would’ve said in university, but let’s bottle that misguided enthusiasm for a moment and carry on.

Because dialogue is not some willing participant in a gimp suit waiting for orders. No, it’s a wild fucking brumby that doesn’t want to be wrangled. And the best way to do so is by doing. But it also pays to watch, or read, the best and learn from them.

You wouldn’t try to wrangle a wild brumby without watching a professional first, would you? No, you’d probably die. Well, you won’t die from writing dialogue without some prior mentoring, but you will quite likely waste a lot of time making mistakes you could’ve avoided.

Who Are the Best Dialogue Writers?

Some people believe that aspiring writers should read books, aspiring screenplay writers should read scripts and aspiring playwrights should read play scripts.

That is bullshit.

Read. Them. All. The scripts for movies, plays and even video games are so invaluable for writing dialogue. This is because dialogue in these three mediums is so important. It’s arguably the best way to learn how to write the speech part of dialogue. Of course, there are plenty of novelists who do this just as well.

When you read books for dialogue, you must also focus on the descriptive and action elements outside of the quotation marks. Although this is similar to stage directions in a play script or descriptive elements in a movie script, dialogue in novels shows you how to add these elements in an engaging way that reveals more to the reader without shoving it down their throat.

So, who should we be reading?

Honestly, there are so many lists out there on the web that you can google “best writers dialogue” and get more sources than you’ll ever want to read in three lifetimes.

For me, the following writers always strike a chord with their dialogue:

Hunter S Thompson – The father of Gonzo wrote about real-life events (other than The Rum Diaries, but even that was autobiographical), so his dialogue was often based off real conversations that he recorded on his dictaphone. What I like about Hunter is that he found a way to make real-life dialogue interesting. It might've been the drugs, but shit that's like saying dry grass invented fire.

Quentin Tarantino – Not many writers can make seemingly bizarre dialogue sound so real and authentic like Tarantino. There’s a poetic flow to the way his characters speak, and it blends so perfectly with the soundtracks to his films.

Tennessee Williams – I remember feeling completely transported to New Orleans while reading Williams’ A Streetcar Named Desire. He taught me how to better capture the sounds and nuances of people from different places, lending authenticity not only to characters, but setting as well.

Richard Linklater – Linklater’s films are very much driven by characters and setting more so than plot. As a result, his dialogue often carries entire scenes and never lets you down.

A little side bar: I’ve found that writers who focus more on characters and setting than plot generally write better dialogue. This isn’t always true, but you’re pretty safe learning from these kinds of writers.

Should Dialogue be Realistic?

Let’s dive a little deeper into something I touched upon with Hunter S Thompson. The man was very, very good at writing realistic dialogue in an interesting and entertaining way.

This is something I’ve always struggled with. I can easily write really boring, mind-numbing dialogue that’s realistic. And I can easily write really out there, crazy, unrealistic dialogue that people don’t actually believe in.

So where the fuck is Goldilocks when you need her?

I imagine that if she were here, she would say something along the lines of:

“When writing dialogue that’s juuust right, you have to make unrealistic dialogue appear authentic, not the other way around.”

“So I shouldn’t try to make realistic dialogue sound interesting?”

“Well, no, you can do that too. Just find whatever is juuust right.”

“What the hell does that mean?”

“Look, I just came down here to get a bowl of porridge and go back to bed. I never wanted to be part of this, so just flubber off will ya.”

Anyway, I guess what I’ve come to realise is that conversation isn’t dialogue. But we have to write dialogue that feels so authentic it reads like a real-life conversation. Whether that involves making completely fabricated dialogue appear real or making real conversations more interesting, there’s a sweet spot right there for great dialogue to live.

And that sweet spot can only be found with practise (and editing). For instance, I had originally included the 'u' 10 times in Goldilocks' "juuust right", but cut it back to three times. Realism, people.

And shit, we’re already so far into this blog and I’ve forgot to mention the most important part, that I’ve learned anyway, about dialogue: subtext.

What is Subtext in Dialogue?

Subtext is essentially the golden “show don’t tell” rule of writing applied to dialogue. Your characters, just like real people, won’t usually say exactly what they’re feeling, thinking or wanting. Instead, they’ll give hints of this through the words they say and how they say them. As readers, we’re forced to read between the lines and fill in the gaps, instead of being told exactly what’s going on.

Time to have a go at writing some very simple dialogue with and without subtext.

The scenario: Mike and Janet are having breakfast together. Mike is angry at Janet for taking money from his wallet the other day.

Dialogue without subtext

“Hey Janet.”

“Yeah Mike?”

“I’m angry at you?”


“Because you took money from my wallet the other day.”

Holy Lucifer that was bad. And unnervingly easy to write. I think I’ve made my point.

Dialogue with subtext

“Hey Janet, can I have some of your bacon?”

“No, you’ve got your own.”


“Hey! I said no.”

“Oh, I’m sorry, I thought we were sharing everything now. Money. Bacon. Money.”

“Jesus, bro, I said I was sorry.”

“And I forgive you.”

“Hey! Stop taking my bacon!”

Fuck, I think that’s pretty good. It took me longer to write, but my god is that conversation a lot more interesting to read. It shows us what Mike is feeling and why, but it also:

1. Tells us more about Mike’s personality

2. Builds conflict

3. Describes more of the setting

4. Reveals the relationship between Janet and Mike

5. Gives the characters distinct voices (kind of)

6. Provides some humour (at least compared to the first version)

Now, when I was writing that second scene of dialogue, I wasn’t thinking about those six purposes. I was only thinking about writing dialogue with subtext, and everything else fell in around it.

So I guess the message to take away here is that once you start focusing on writing dialogue with subtext, your dialogue will naturally begin to serve multiple purposes without you even trying. This is why, in my mind, subtext is the most important part of writing good dialogue.

Writing without subtext, or telling instead of showing, also makes readers feel like the author perceives them to be too stupid to read between the lines. It’s a mistake I’ve made constantly with my writing, due to a lack of practice and confidence in the craft. But that’s all it is. Practising writing with subtext is all it takes to do it consistently and well.

And yet again we find exceptions to the rule. Many iconic lines in novels, films and plays don’t have subtext. But as I said, before we break the rules, we should probably master them, or at least know what they are.

This seems like as good a place as any to bring this first lesson to a close. If you’ve made it this far and are feeling a little disappointed, then let me point you in the direction of some resources that might actually help.

Check out these websites:

12 Tips for Writing Dialogue – Ginny Wiehardt

How to Write Good Dialogue – Nathan Bransford

Top 10 Best Dialogue Movies – Taylor Holmes

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