Your Ultimate Guide To Writing Emails That Are Actually Funny

There are funny emails, and then there are ‘funny’ emails, and the chances are pretty good that you already know what I mean by the latter.

You see, humor can be a delicate thing. Even at its broadest, it’s somewhat subjective, and the more specific you get, the more easily you can lose people.

And there are few things that will put people off more than a painfully-unfunny email.

But why is this the case? How do you avoid deploying a clunker? And what’s the secret to online hilarity, if there even is one? (Note: there certainly isn’t).

Let’s take a look at the things you can do to avoid comedy disaster, and we’ll keep the wacky hijinks to a minimum to avoid a horribly-ironic fate. Here we go.

Keep Them Short

How long should a sales email be? If you thought something other than “Between 50 and 125 words”, you’re apparently wrong (at least, according to a statistical study).

Maybe your funny emails aren’t going to be about sales, that’s true. But it remains the case that people don’t like reading long emails, no matter how compelling.

The internet is a minefield of distractions.

Besides, you don’t need all that many words to make an impact. A little can go a long way. It’s true for this section, and it’s true for comedy in general.

Tip: Use these powerful words to supercharge your funny emails!

Use Humor As an Accessory

Imagine that you’re having a pleasant conversation with a stranger, but all of a sudden, totally out of nowhere, they make a dreadful, horrible, diabolical joke, delivered with entirely-forced cheeriness. You stop yourself from visibly cringing, but inside you’re suffering.

After that, you just can’t focus on what they’re saying, and you definitely can’t take them seriously. Your paths have fully diverged, never to meet again.

two path road

The way to avoid this kind of fate with email comedy is to avoid placing too much stress on any one part. It should only ever support the ultimate purpose of the email. At no point should any metaphor or silly word be given enough focus to slow or stop the flow.

Try to envision the humor you put into your emails consisting of, as customer service in general is here described, little unexpected extras. It’s all about delighting in ways that are unexpected and surprising, not blatant and over-wrought.

Instead of detracting from the points you make, questions you ask, value you add and actions you suggest, they should bolster them with a nice, friendly, welcoming feeling that the reader will appreciate.

That means you should steer clear of jokes in general. The occasional brief and seamless aside can work if implemented very carefully, but most of the time a joke in an email will be clumsy and obvious and generate second-hand embarrassment in all those who read it.

If you can’t be genuinely funny, at least to a very mild extent, then you’re far better off getting rid of all traces of attempted humor, because they only stand to sabotage your efforts.

Stay Audience-Appropriate (But Don’t Pander)

Whatever you do, whatever style of humor you lean towards, you must make sure that it actually stands a decent chance of being appreciated by your target audience.

To do this, you need to take into account the tone, language, and references of the intended recipients, and cater to them when necessary. Comedy relies heavily on references to shared experiences.

It may be that your audience consists of people much like you, in which case this part should be easy. Just talk as though you’re addressing your peers.

If you’re a middle-aged curmudgeon going to fire off a newsletter to a youthful audience, however, definitely do not wheel out a dated reference to an obscure musician from your childhood. It won’t play very well.


For the sake of illustration, let’s pretend that this sign is very old.

With that said, while you do want to take out anything that won’t be understood, that’s not to say that you should throw in a lot of references that will be understood, just for the sake of it.

You can show that you understand your audience’s needs and preferences without trying to gain entrance to their gang. Besides, you need to stay true to yourself, as we’ll see next.

Draw From Your Personality

Forget rifling through scripts to old comedy routines or ebooks called “501 Ways To Be Hilarious In Business”. You need to say things that match who you are.

Authenticity is a nebulous but powerful influencer, and no amount of ripping off a funny webcomic you saw last week is going to help you achieve it.

If you find something funny, let people know. Even if they don’t find the same thing funny, they will find something to enjoy in your enjoyment of it. We’re all more inclined to like people who come across as open and genuine, and in turn more likely to laugh along with them.

genuine fake factory

Pictured: a very confusing sign. Avoid this!

This is also a great way of making your brand memorable. The more you lean into that signature tone, the more likely you are to stick in the reader’s mind.

In a good way, hopefully.

It does depend on your personality (as well as the quality of your email design in general). And that leads us to the next point.

Get Plenty of Opinions

This may be the most important thing you can do when it comes to producing a funny email. Draft something however you like, then have people you know read it. Friends, partners, colleagues; all are perfectly capable of providing invaluable feedback.

The reason this is vital is that the subjective qualities in humor can lead some people to believe that having fun writing something must mean that it’ll be fun to read.

Ask a professional comedian and they’ll tell you it isn’t true. They may even glare at you.

scary and funny face

Pictured: a furious comedian. Possibly. He could be a pilot for all I know.

It’s technically possible that your personality-driven draft will be a superb work right off the bat, but it’s considerably more likely that it needs work first. Not to take out everything, but to pick out the worst bits and polish the mediocre ones.

“It might not seem like it, but the best comedians hone their material scientifically, by experimenting bit by bit,” says Warner. “And the only way to learn is through hard, repetitive, empirical work. You get up there on that stage night after night, gauge which lines work and which don’t, and adjust accordingly.”

Now, you should be doing this for a lot of your standard emails anyway, but it’s so much more pressing here because comedy is a high-risk, high-reward tactic.

The more feedback you get, the more you can polish your email, and the better it will end up coming across to the readers. There’s no substitute for editing.

Remember Not To Take Things (Including Yourself) Too Seriously

In the fast-paced world of business, it’s pretty common for people to become very sensitive and controlling about how they come across to clients, customers, colleagues, and competitors alike.

You may be tempted to joke about your professional rivals, and that’s alright, you can. Just keep things light, and don’t make the great error of taking yourself too seriously.

Comedy abhors the self-important. If you can show that, while you are very serious about what you do, you’re still willing to poke fun at yourself… well, that’ll help immensely.

So let’s recap. Be yourself, know your audience, get feedback, and don’t take things too seriously. Then edit, edit, and edit some more. That’s really all it comes down to. Good luck!

Victoria Greene is an eCommerce marketing expert and freelance writer who knows the importance of personality in business. She particularly enjoys encouraging companies to embrace their unique strengths. You can read more of her work on her blog Victoria Ecommerce.

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