4 Mistakes to Avoid When You’re Trying to Convert with Funny Copy

You know when someone tells a joke, and they’re super excited about it, and you’re waiting for the punchline…

And then the punchline comes, and that poor lil joke falls flat on its face?

r2d2 fallsWomp.

Maybe that’s happened to you. It’s DEFINITELY happened me. More than once.

*cue silent, awkward foot shuffling *

The same thing can happen when you’re trying to write funny copy.

And along with your joke falling flat, you don’t get your point across…

And with that failed punchline and missed point go all hope of convincing or converting your readers.

If your joke is REALLY bad, your readers might not even like you anymore. 🙁

luke nooooAnd as we know, being liked is the only reason to continue existing.

Now, I can’t tell you what jokes will have your readers rolling on the floor like those stupid jingle-ball cat toys I inexplicably have forty of.

What I CAN do is tell you about 4 common mistakes I see in so-called “funny copy”. These faux pas suck the air out of a joke faster than the vacuum of space deflates our puny human lungs.

^^ Observe! An in-the-wild example of a joke that didn’t quiiiite get there.

Mistake #1: Forcing the joke

If a joke takes an entire extra sentence, a series of hyphens, or a personal phone call to explain, it’s just not obvious enough.

Forcing a joke creates an agonizingly awkward experience. And that experience makes the rest of your copy less effective.

Unclear, obtuse, and poorly phrased jokes add to your readers’ cognitive load. Their brains literally have to burn more sugar just to try to understand you.

That’s brain-sugar they’re NOT using to think about how convincing your offer is.

luke and yodaMmm, sugar.

One quick and easy way to simplify a joke? End your sentence on or near the funniest word.

For example, take this dumb bit I used to perform:

I like to replace the words “kid,” “child,” and “baby” with “possum” because it just sounds so much better when other women talk down to me. “Everything is different once you have a possum, Lianna.” “I didn’t know what love was until I met my possum.” “I needed reconstructive surgery after giving birth to my possum.”

Possum is a hilarious word. And it’s the main reason that bit got laughs. ‘Cause let’s be real, it’s not my finest work.

Mistake #2: Too many jokes

Look, I’m a firm believer that the more puns, the better. Punning is my favorite pastime.

In fact, I was crowned the Pun Champun of New Orleans at the first International House of Puncakes competition in 2017. (It’s not actually international, but who could miss the chance for that name?)

lianna pun competition

You were expecting another Star Wars GIF, weren’t you?

I make a punishing number of puns — so many puns, some people find it punbelievable!

BUT. I also try to kill my darlings when I’m writing copy…

Because, just like forcing the joke (Mistake #1), including too many jokes can distract readers from the real point of your copy.

And that’s a losing proposition.


Y’all see “Star Wars: The Last Jedi”? Sure, it was good, but it had like 25 different openings.

In my incredibly humble but also completely accurate and inarguable opinion, “The Last Jedi” would have been a lot stronger if there had been just one or two different establishing scenes. Instead of the seventeen opening scenes that just made it feel like the movie was constantly starting over like Groundhog Day.

darth maul

Yeah, I said it. COME AT ME, NERDS

There isn’t really a hard-and-fast rule for how many jokes you should make in a piece of copy, but in case you need one, I made it for you:


This should keep us all sane and on track.

Also, obviously this rule doesn’t apply to me. Because I said so. *stamps foot*

Mistake #3: Failing to voice-match

One of the most common issues brands and writers make when they’re starting to experiment with humor? Failing to match their voice with the brand’s existing voice.

OR, a brand goes full-bore with customer-facing humor from the start… but they forget to update the default copy in their email service platform or CMS.

So you get this maniacal mix of fun, punchy, branded copy — and boring-ass transactional emails.

For example, here’s what happens when you subscribe to McSweeney’s, which you’d think would have side-splittingly great copy even in its default emails:

mcsweeney's meh

You would be wrong.

Dang! So disappointing.

Attention to detail is always important when it comes to copy, but it’s extra crucial when you’re aiming to be funny.

Mistake #4: Jokes in the wrong spot

Rhythm is one of the basic principles of comedy. Whether you’re watching standup, improv, sketch, or your spaghetti-stained Uncle Joe reminiscing about his youth, you’re subconsciously expecting some sort of rhythm and resolution.

When you make a joke at the wrong spot in your copy, you destroy the rhythm. You pull readers away from your point.

Including a joke at the wrong spot can even feel frustrating or irritating, much like including too many jokes.

it's a trap

If this all feels overwhelming, you could just hire me

So where are the RIGHT spots for a joke in your copy?

Anywhere you’re introducing anxiety or doubt — Because humor breaks tension and builds trust. I especially like a little bit of humor in “click trigger” copy under a CTA button

Anywhere you’ve got a long list of boring or “standard” items — Add delight here with a funny line item and reward readers who are paying attention

Anywhere your reader runs the risk of getting bored — Long, technical copy? Make a parenthetical aside every now and then

Anywhere you’re talking about yourself and your brand — Show readers and customers that you’re confident enough to be self-deprecating. It’s paradoxically endearing

In your image captions — Everybody reads the captions. Everybody. Even you


These are all extra-safe options, because the object of your joke is never the reader.

(Wanna make fun of your reader? SO DO I. PLEASE STEP INTO MY OFFICE)

Anyway, I figured a post about everything you’re doing wrong would be a great way to make you like me more.

Did it work?


  1. Matt Reply January 16, 2019 - 1:54 am

    Ya nailed it! Always love to read and learn from your copy Master Li-oda >> that’s not so punny, I know. 😬

    And I’ll forgive you for the Last Jedi comment because I know you were just saying that set up a punchline. 😒

    “Am I wrong Dude? Am I wrong?! Tell me I’m wrong Dude…”

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