Pages Newsletter Tips
How to Use Humor
The hardest thing to write, and the easiest to get wrong. Aim for a smile, not a laugh.
Here’s the honest truth about humor: it’s the hardest thing in the whole newsletter to write, and the easiest to get wrong. A joke that misfires doesn’t just fall flat — it brings phone calls. But the good news is you don’t have to be a comedian, and trying to be one is actually the whole problem. The goal isn’t the big laugh; it’s the warm smile. Light and friendly is safer, it suits a newsletter better, and it lands more reliably than a joke that’s reaching. Nearly every humor disaster starts the same way — with someone going for the laugh.
the big laugh
The six rules
Mostly ways to keep a friendly joke from becoming an accidental one.
Aim for a smile, not a laugh
The reach for the big laugh is where the trouble lives — it’s what tempts you toward the sharp, the edgy, the joke at someone’s expense. A gentle, friendly smile is safer, fits the tone of a newsletter, and honestly lands more often. Undersell it. Nobody ever got an angry call about being too warm.
Make the subject the joke — not a person or a group
The safest humor is about a thing everyone already finds funny: fair food, Monday mornings, the office copier that jams on principle. The topic is the only butt of the joke, so there’s no one to offend. Point at the funny thing and let readers laugh at it together.
Write for a reader with no context
Print strips away your voice, your face, and — crucially — who said it first. A joke that’s perfectly fine in one person’s mouth can read as cruel with the teller removed. If a joke needs a tone, a wink, or knowing who’s telling it to be okay, it will not survive on the page. When in doubt, assume the reader knows nothing but the words.
Never punch down
Aim up, sideways, or at a foible we all share — never down at a group, never at the vulnerable, and never at the reader. If the humor needs a target, let it be you, the weather, or the situation. A newsletter should feel like it’s laughing with its community, never at anyone in it.
Match the room
Audience and newsletter type change what lands. A warm ribbing that’s perfect in a community paper can be a real problem in an employee newsletter, where the same line reads very differently with a boss looking on. Before a joke goes in, picture exactly who’s holding the page.
Treat your own certainty as a warning light
Good intentions are precisely what make you stop checking — the joke you’re sure is harmless is the one that needs a second reader. When you catch yourself thinking “they’ll love this,” that’s your cue to show it to someone unlike you first. And if you’d have to explain why it’s funny, it’s already dead — cut it.
See it in action
The same warmth, aimed well and aimed poorly.
“Deep-fried butter is back at the fair this year — because apparently regular butter just wasn’t trying hard enough.”
The subject is the joke. Everyone already agrees fair food is gloriously absurd, so nobody’s the butt but the corn dog.
A one-liner lifted from a comedian and dropped into the jokes column — the kind that’s only okay if you know who’s telling it.
Print deletes the teller. With no idea who said it first, readers hear it in your newsletter’s voice, and a joke that was fine in its original mouth can land as an insult.
“Sadie and Dave, practicing for retirement” — under a photo of a man and his dog fast asleep on the couch.
Affectionate, obvious from the picture, and it’s the family’s own gentle joke about themselves. Warm, and aimed at no one.
“Hard at work as always” — under a photo of a dozing employee, in a company newsletter.
Same warmth, wrong room. Now it reads as calling a coworker lazy, in print, with the boss reading too.
The one reliable recipe
When you want a little fun and none of the risk, point at something everyone already finds funny — the weather, fair food, a Monday, the copier that never works — and just describe it a touch too honestly. You’re not making a joke so much as holding up the thing and letting everyone laugh at it together. No target, no trouble, and it still feels like fun.
The humor gut-check
- Am I aiming for a smile, not a big laugh?
- Is the subject the joke — not a person or a group?
- Would it still be okay to a reader who has zero context?
- Does it punch down at anyone?
- Right room — does it fit this audience and this newsletter?
- Am I a little too sure? (If so, show someone unlike me first.)
- Would I have to explain why it’s funny? (If so, it’s already dead.)
Nobody ever called to complain about a gentle smile. Aim there, keep it kind, and when you’re not sure — warm beats witty, every time.
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