I like to think I’m funny.

I mean, I’ve made people laugh. I think.

Probably.

I hope.

But mostly, I make myself laugh. A lot.

Which is honestly a great skill to have.

Because even if no one else is entertained, at least I am.

(And if that’s not self-care, I don’t know what is.)

But you know what actually is funny?

Like, objectively funny?

Like, makes people stop, chuckle, and maybe even screenshot it funny?

Microcopy.

The right words, in the right moment, with just the right amount of personality in a product, can turn an average user experience into something memorable.

And the best part is that microcopy doesn’t just entertain the user.

It guides. It reassures. It makes people feel seen.

However, just because funny microcopy works in some products doesn’t mean it works for all.

That’s because, as impossible as it might be to believe (considering how absolutely awesome those little sentences can be), great microcopy isn’t just about clever wording. It’s about context.

So, in this issue, I’ll break down different types of microcopy that bring products to life, why and when they work so well, and when they might actually backfire.

For Context…(yes, pun intended)

If you're not familiar with the term “Microcopy”, this is what it sometimes looks like 👇

And this is what it means 👇

Microcopy is the small but essential text that guides, informs, or reassures users in digital experiences.

It appears in buttons, error messages, form fields, tooltips, onboarding prompts, empty states, success messages, and loading screens. Basically, anywhere users need clarity or a little nudge to take action.

Microcopy appears everywhere, but for this take, we’re zooming in on one angle: humor.

Now, back to the main stuff…

Types of Microcopy

^{Disclaimer: Some example copy used here might no longer exist on the specified platform. This is because product teams like to overhaul things, particularly copy (even perfectly good ones) when trying to give the product a ‘new look’.}

^{Mini-rant done. Again, back to the main stuff…}

1. The “Witty But Useful” Microcopy

This is the microcopy that makes you laugh and keeps you on track. It doesn’t just throw in jokes for the sake of it but actually helps.

Example:

→ Slack’s loading screens: "What do you call a can opener that doesn’t work? A can’t opener."

→ Spotify’s error messages: "Oops. Something went wrong. (It’s probably the WiFi’s fault.)"

Why it works:

It acknowledges the situation, reduces frustration, and keeps the experience smooth.

Where it makes sense:

Loading screens, error messages, 404 pages.

Where it doesn’t work:

A banking app. If you’re trying to transfer money and an error pops up, the last thing you want is a joke. You want a fix.

2. The “Hype You Up” Microcopy

This is the copy that makes you feel like you just won an award for doing the bare minimum.

Example:

→ Duolingo when you’re taking a lesson: "You’re on fire! Keep going!"

(I particularly love the ‘buhbeem’ sound Duo makes when you answer 5 or 10 questions correctly in a row.)

→ Headspace after a meditation: "That’s a wrap! Your brain thanks you."

Why it works:

People like positive reinforcement. A small “Good job!” at the right moment makes the experience feel rewarding.

Where it makes sense:

Progress updates, achievements, milestones.

Where it doesn’t work:

WhatsApp. Messaging isn’t built for achievements but for connection. Adding gamified microcopy here would feel weird and unnecessary.

3. The “Overly Honest” Microcopy

This is the type of copy that makes users laugh because it says what everyone is thinking.

Example:

→ Mailchimp’s unsubscribe message: "Wait… is it something we said?"

→ Tumblr’s password reset: "Don’t worry, it happens to the best of us."

Why it works:

It feels human. It acknowledges that users are real people making real decisions, and sometimes, a little honesty goes a long way.

Where it makes sense:

Confirmation messages, email signups, unsubscribe pages.

Where it doesn’t work:

A mental health app. If someone is deleting their account on a therapy platform, humor might come off as insensitive. Instead, the copy should be supportive, not snarky.

4. The “You’re in on the Joke” Microcopy

This is the microcopy that makes users feel like they’re part of an inside joke.

Example:

→ Cookie banner: "We use cookies. Unfortunately, not the kind you can eat."

→ Password strength checker: "Weak. Like decaf coffee."

Why it works:

It builds a connection. When users feel like a product gets them, they trust it more.

Where it makes sense:

Tooltips, security messages, pop-ups.

Where it doesn’t work:

Government websites. If you’re filling out a tax form, a joke about how “tax season is a nightmare” isn’t helpful; it’s frustrating (especially with how bad the UX is on many gov-sites).

So, Why Does Context Matter?

A lot of people think good microcopy just means adding personality.

It’s easy to see a fun, witty microcopy and think, We should do that too!

But it’s important to stop and note that what makes those eye-catching microcopy stand out isn’t how entertaining they are; it’s how they fit the context of the product and the user’s mindset.

Take WhatsApp, for example.

You won’t find playful loading screens or quirky error messages there.

And it’s not because WhatsApp’s writers aren’t creative but because the context doesn’t call for it.

People don’t open WhatsApp for entertainment in the conventional way.

They’re there to message someone or watch statuses, not to engage with the app itself. A joke on a loading screen would just feel like a distraction, and the core function of WhatsApp is distracting enough, let’s be honest.

Now compare that to Slack.

Slack is a work tool, but work can be stressful, overwhelming, and repetitive.

That’s why their playful loading screens work.

They provide a small moment of humor that actually improves the user experience.

You could be giggling about the cute pony in the Unreads tab and forget that the reason you saw it in the first place was because you were going through the 100s of messages you missed over the weekend.

Or think about a mental health app.

Imagine if it used the same witty tone as Duolingo:

“C’mon, you can do this! You’re just one therapy session away from crushing it!”

That would be completely off.

Instead, a mental health app needs a voice that is supportive, kind, and calming, because that’s what users need in that moment.

If you need a key takeaway from all I’ve said here, then this is it: Every product has its own context (what feels right for the product, the user, and the situation), and the best microcopy fits that context perfectly.

Your Turn (Context Checklist)

Next time you’re writing microcopy, ask yourself:

✅ What is the user feeling at this moment? (Frustrated? Excited? Stressed?)

✅ Does this actually help the user or is it just being clever for the sake of it?

✅ Does this tone match the overall voice of the product?

✅ Does it fit the product’s context?

If the answer is yes, you’re on the right track.

And if the answer is no?

Well… you could always throw in a bad pun.

That usually works too.

2025 with Content & Context 🤝 

This year, I want to take you on a journey.

Not just through my takes on what content founded on better context looks like (it looks pretty good actually), but through the world of UX writing itself. What it is, what it isn’t, and why it matters in product UX in general.

And because you’ve been with me through this journey so far, I’ve put together something special: a free resource, UX Writing for Small Teams. It’s my way of saying thank you and making sure that even if you don’t have a UX writer on your team yet, you can start creating better experiences right now.

You can grab it here.

Now I know this resource may not be beneficial for everyone, so if you have a special resource request, please reach out by replying to this email with what would be beneficial to you. That’s what UX is about, really.

New Here? Catch Up on These Reads

Here are a few past articles you might enjoy:

•  B-rated... 

•  How to "unalive" a good product idea 

•  This thing called UX writing... *sigh 

•  👋 First impressions only happen once 

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