How to Write an Unforgettable Opening Line

This is hard for me to say, fans of Stories’ Matter, but… I’m dying of cancer. This may be the last video I ever publish.

Okay, not really. But that got your attention, didn’t it? Made you want to keep reading.

Fiction, at its most fundamental nature, is all about lying. It’s about tricks and deceit and pulling the wool from behind your reader’s eyes. As a fiction writer, you use big words to lie and make yourself appear smart and distract others from the fact that, if the apocalypse were to come, your uselessness to mankind would make you one of the first left behind to die.  

The hook is the cornerstone to this deception. It’s the flashing titty, the taste of that first sip of absinthe, the smell of newly-lit rock smoldering in the crackpipe. It’s there to blind the reader to the crooked teeth, the blinding hangover, the achy withdrawal and the kiss of concrete in the back alley.

In today’s article, we’ll see how we can effectively snatch our reader’s attention right off the bat. We’ll manipulate in a way that would get us fired from almost any other job on this edition of Stories Matter.

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Before we start, let’s look at some examples of great opening hooks from classic works of fiction.

“I am an invisible man.”

From Invisible Man by Ralph Ellison. This is a great opening for people who don’t read the titles of books they’re reading.

“riverrun, past Eve and Adam’s, from serve of shore to bend of bay, brings us by a commodious vicus of recirculation back to Howth Castle and Environs.”

From Finnegan’s Wake by James Joyce. As true today as whenever it was written.

“You want to be there. You know you do. Don’t lie, dahling. I know what you think when you look up at that splendorous place atop the mountain. I know what fills you, spurs you on, fuels your dreams. You’re obsessed with being chosen. Everyone is.”

From Modelland by Tyra Banks. There’s so much confidence in the prose here, such command of the language. You can tell Tyra’s going to hit you with truths other models/talk show hosts wouldn’t dream of.  

So, how can we be as effective as these three?

Step One: Start in the middle of the action

This is sometimes referred to as “in medias res,” which is Latin for “Things called media, they go to the middle.” Starting this way confuses your reader. Which is good because most people read books to appear smart. So this forces your reader to keep reading to find clarity so they feel like less of a dumbass. Using tricks to prey on the insecurities of your reader is what writing’s all about.

Step Two: Imply intriguing contexts

It’s not just about confusing your reader. And it’s not just about shocking your reader with mutilations and expletives and left-wing ideas like murdering anyone who says Merry Christmas instead of Happy Holidays.

A context could be an era, place or scenario. You could allude to an ongoing conflict or bring up an interesting fact about a place or era of history.

Here’s how I started Doe’s Boys, my World War II drama set in the North African theater:

“By the end of 1944, half the men in L Division would never return home. Most of those who did came back missing a body part or two. But everyone who came back whole had one pastry chef to thank.”

Step Three: Set the voice and tone

We often think of hooks as being plot dependent, but voice and tone matter just as much. If they’re anything like me, the average reader is going to spend the next month or so listening to this person, so they want it to be someone unlike their family or co-workers or therapist, somebody worth listening to.

From the opening lines of Kerouac’s On The Road, you can tell Sal Paradise is a free spirit, not someone brought down by the old ball and chain.

You could try being funny, but I’d recommend something sad and desperate. If YouTube analytics are to be trusted, that will come much more naturally to you.  

Step Four: Invite controversy

Rudyard Kipling once began a story this way:

“A man should, whatever happens, keep to his own caste, race and breed. Let the White go to the White and the Black to the Black. Then, whatever trouble falls is in the ordinary course of things – neither sudden, alien nor unexpected.”

Now, am I suggesting you start your story advocating racial segregation? Kinda. I mean, Kipling’s famous and you aren’t so he must be on to something.

But if blatant racism, sexism, homophobia, zoophilia make you uncomfortable, just choose a statement that shows a strong but understandable conviction. My 2020 crime epic A Handful of Napalm starts like this:

“The one thing nobody ever tells you about crack: It never stops being awesome.”

Step Five: Tug the heartstrings

This seems counterintuitive as your reader doesn’t even know the character yet so why would they feel an emotional connection? Sort of like how you ignore news stories about thousands dying in floods and earthquakes or force yourself not to learn co-workers names so they won’t get attached and ask you to give money to their GoFundMe when they get bone marrow cancer.

There are, however, certain universal emotional triggers that even people who walk past choking homeless people without a second thought can’t ignore: A crying baby. A barren woman. A barren woman’s dog about to be put down for biting a crying baby.

Here’s a great example of how to do this:

“I was insane the way an animal is insane because I’d lost everything.”

That’s from William Shatner’s biography and it gets directly to the heart of his pain and his struggle.

Want to Write a Great First Chapter? Treat It Like a First Date

The first chapter of your book is a lot like a first date. Whether you hope to boost your book sales or have a partner who can call emergency services if you suffer a stroke in the middle of the night, you have to make a good impression quickly.

While your book cover, review and endorsement quotes are more akin to social media dating profiles, flirty texts and dick pics, the first chapter is much like a first date, where your reader can get to know the real you.

But as anyone who has been on a first date or has sent their first chapter to a publisher can tell you, this is when audience scrutiny is at its highest. Just as a date might be looking for annoying eating habits, Nazi tattoos or evidence that you’re placing sports bets while she’s talking about her job, your reader is looking for intriguing mystery, a unique voice or well-developed world building.

In this article, I’ll show you how the strategies that you can use to get laid on a first date will work equally well in the first chapter of your novel. We’ll hide our desperation to be noticed on this edition of Stories’ Matter.

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Strategy One – The Sympathy Strategy

I use this all the time on first dates. My goal is to make my date feel sorry for me so she’ll be less likely to turn down my advances. I have a few go-to’s. Sometimes I’ll tell her my last wife hurt me because was a total crazy bitch. This makes me look like a reasonable guy who’s just unlucky, and it has the added benefit of boosting her confidence because she’ll feel normal in comparison.

Other times I will pull out a photo of my “dead son” quote-unquote, which is actually a photo of a real child from a missing person’s cold case. This shows I’m committed enough to being a father, and the woman, who in the age range I date is likely baby crazy, will naturally assume I want to have another child quickly to take the place of the one I’ve lost.

In a book, you similarly want your reader to identify emotionally with your character fairly quickly. Books take a lot more time and effort than almost any other type of entertainment, so those emotional bonds are necessary. Consider starting your book at a parent’s funeral, or if you want to keep it lighter, just make it a dog funeral.

Strategy Two – The Exotic Setting

If there’s one thing I know about women, it’s that they’re wary of going to your house on a first date. If there’s two things I know, it’s that they really don’t like going to your house on a first date when you forgot to close the dresser that contains mementos and clothes from all your previous wives.

An exotic location can be a great place for a first date. If nothing else, the crazy setting gives you something to talk about. Some of my go to’s are restaurants where you can eat sushi off of naked people and spas where naked people come to eat food off of you.

In fiction, land your reader onto the surface of an alien planet. Lower them in the depths of an African cobalt mine. Or borrow from real life and use my naked spa idea.

Strategy Three – The Info Dump

Sometimes, when you’re on a date, it’s best to lay all of your cards on the proverbial chess table. Especially at my age, when cancer or heart disease might take you during your next sexual encounter. Well, heart disease anyway, I’ve never heard of a cancer that killed someone during sex, but at the same time, I’m not an oncologist so I can’t say with any certainty that there isn’t a type of terminal cancer that’s onset by particularly vigorous intercourse.

Anyway, my point is, I often make it a point to start dates by cataloging my marriages, my recent sexual history, the children that I know about, my publishing feats, my bankruptcies, my mixed feelings about being partially raised by a prostitute and my regrets that I never DNA tested the man in my father’s grave. And generally, I try to get this all out of the way before the main course arrives so we can just enjoy our meal. Sometimes the date leaves before then, but I’m at least happy knowing neither of us has wasted our time.

Now, a lot of writers will tell you it’s wrong to info dump right away. I disagree. You merely need to find a way to do it that doesn’t feel like info dumping. Epistolary devices like news articles or diary entries work great. In The Life We Have, the lead couple looks through a photo album together and discusses the last ten years of their marriage. To make it less boring, I end the chapter with a raunchy sex scene.

Strategy Four – The Misdirection Strategy

Like a reader, a potential love interest is out for an element of surprise. Some people think dating is about connection and comfort, but comfort is just sitting at home alone, binging Netflix and seeing how many boxes of wine you can drink before you pass out.

People date to get out of their comfort zone. I like to keep my dates on their toes. Sometimes I’ll spend the whole date hinting at my sexual prowess by doing things like running my fingers suggestively up and down the stem of my wine glass or sharing photos from a recent vacation that “accidentally” contains one in the middle of me shirtless in front of a mirror. I may also compliment the mouth of my potential paramour.

But then, at the end of the date, instead of suggesting we go back to my place, I’ll end things with a hearty, chaste handshake. “Who is this man?” say her eyes as we depart for the night and the thought of her tossing and turning in her bed unable to get me out of her mind is almost as erotic as the eventually sexual eruption that is soon to follow.

Of course, I have realized that the opposite strategy, hinting at chastity and wanting to take it slow, only to end the night with a sudden, desperate plea for at least a handjob, is not as successful.

Anyway, this type of misdirection can work wonderfully in your fiction. You could start the book from the perspective of someone who turns out to be an ancillary character, or a mystery that doesn’t actually play a part in the main plot. My novel, The House on Pain Avenue, starts with the protagonist finding a dead body in the park. But this isn’t a story about solving that mystery. It turns out it’s merely a catalyst for getting the main character to get checked for syphilis.

Strategy Five – The Unusual POV Strategy

Now this is a strategy I’ve used less than the others, but it can be successful when implemented well. In the context of dating, what I mean by POV is giving my date a fake name and sometimes even a fake persona. Now, why would I do this?

Well, for starters, sometimes I want to make sure I’m not dating a fan. Sometimes they get clingy and sometimes they get a little too critical. But what I’ve found, ironically, is that pretending I’m someone else is really freeing and helps me relax during the date. I’m much less self-conscious about being mean to waiters who won’t let me order off the menu. I’m also much my forward about which of my partner’s body parts I like and which could still use a little work.

 In your novel, you could start the story from the perspective of a dead person, a villain trying to justify their crimes, or as in my novel, Plastered Bastard, the perspective of the car the drunken main character is driving.