A big statement.
It doesn’t matter whether they appear on a blog post, a commercial, an advertising message, a business book, or a novel.
Headlines need to capture attention and draw people in. They can be bold, intriguing, mysterious, desire-enhancing, problem-solving, promising, dramatic, or even… funny.
But they need to be intentionally funny!
Funny is one of the hardest things to achieve in copywriting and in any kind of writing because it requires a fine-tuned set of skills.
The writer of funny needs to 1) understand the audience’s worldview perfectly, and 2) be able to merge that worldview with an unexpected and innovative idea the delights without offending.
Last week, we took a look at the latest Equinox ad campaign that has pretty much failed on both these fronts: It doesn’t seem to understand or acknowledge the gym-going audience’s worldview, and the “twists” it presents are a little too twisted (almost offensive at points) to be funny.
But another epic way headlines can fail is when they become unintentionally funny. When people laugh not with you for creating a delightful image in their minds, but at you! Gulp!
These unintentionally funny headlines will have your in tears and show you how to avoid the same mistakes as we analyze what went wrong.
Ready? Grab a tissue and let’s get started!
1. When You Know What YOU Want to Say
That’s the trick about getting the worldview right. You have to understand that your audience doesn’t have the complete image, all the information, or the entire story in their heads yet.
And it’s your headline’s job to draw them in with a strong hook. But when that hook tries to get too much at once… oh boy!

Instead, she just sounds like a perv. Offering girls “something special” by means of her position as… head!
Because the word “head” can have various uses ranging a very wide spectrum of meanings, it easily lends itself to misreading and double-entendres when you don’t stop to think if people who don’t know the story understand what you mean:

This headline needed proofreading by someone who wasn’t in the story and didn’t know what the headline meant, or what the author had in mind with “head job,” but actually read it at face value.
If you don’t have an “external reader” for your messages (like a friend, a collaborator, or even your mom), try to at least let them sit overnight before publishing. Looking an “inside” headline with fresh eyes will often help you catch such communication errors.
2. When You Really Needed to Open That Thesaurus
When you realize for example that you used the word “powerful” too much and instead of finding new ways to convey your message your resort to substituting “powerful” with words like “forceful,” “violent,” and “intense” all of which carry different intonations and color a message quite differently.
Because there aren’t really any substitutes for the right word. The right word is the right word.
And the moment you need to run to your thesaurus (as I constantly do as a professional writer) is when you haven’t hit upon that right word quite yet.
Because wrong words can leave you committing blunders like the following:

This headline makes me feel guilty at laughing at the incongruity. And guilt is never a good tactic when you’re trying to communicate anything to an audience.
Yet a slight change following a 2-second search in the thesaurus could save this author all the embarrassment.
How about instead of “applauds” using a word like “praises,” “commends,” or “appreciates”? All better alternatives. All still portray the same meaning.
3. When You Shoot for the General and Miss the Target
Being specific, however, doesn’t mean compacting the entire meaning of the article, sales page, or any other communication in the headline. (See the girls’ school headline above!)
Nor does it mean being overly generic as to avoid giving too much away in the headline. Have a look at the following exhibit:

Could the message of this article have been that the shaking occurring during earthquakes causes most damage? I highly doubt it. That’s worse than old news. It’s common sense.
If you look at the sentence below the headline, it dives into the causes of the varying degrees of earthquake shaking. And perhaps the story explains how different types or intensities of earthquake shaking damage buildings.
In which case the headline could read:
“How Various Earthquake Shaking Patterns Cause Damage.”
Or
“How Earthquake Shaking Damages Buildings.”
Or something similar that revealed what the article was about.
Stating the common-sense or the obvious only makes readers wave your text aside. “Yeah, yeah, we already know what.” What is your real point in the communication?
4. When You’re Entirely Clueless About Your Audience’s Worldview
The web coder with the ugly website that’s entirely functional. The talented interior designer who speaks entirely in highfalutin jargon. The life coach who mocks “silly” emotional failures.
All three scenarios stem from a lack of true understanding about who your audience is and where you need to meet them. And so you end up sounding condescending and offensive to the very audience you’re trying to reach.
And it can come out in as little as a headline you write if you’re not in touch with your audience’s worldview.

“Should I read this article or is it belittling to the man in the story?”
“Who’s belittling whom here?”
“Is this supposed to be funny?”
Or how about this headline:

Breaking with the audience’s expectations in this way and opening up a gap between what the headline purportedly says and the actual feeling it conveys can turn people off your message faster than anything else.
5. When You Get Your Facts Twisted
Clarity is the main aim of any communication. And when clarity is violated… funny things can happen. Funny at your expense that is. Because they can cause you big bucks if they happen in advertising headlines.
Take these newspaper headlines as examples:

And a wrongly stated advertising messaging can have the same disastrous effects on your business: Cause people to lose their trust in you.
Or how about this:

If you read the bit of text visible with the paper clipping, it seems that what the Utah Poison Control Center is really reminding people is that medicine, when badly administered, safeguarded, or presented, can become poisonous for young children.
The author’s blunder is the headline, funny as it may be, must have robbed many parents of the chance to be informed about poisoning dangers around the house. Because we all know we shouldn’t take poison. Thanks very much for the “reminder” Utah Poison Control Center but I don’t think I’ll be reading on…