Making Jokes at Someone s Expense

Making Jokes at Someone’s Expense – Why It’s Tricky

Humor can be a great way to connect with people, but when it’s aimed at someone else’s expense, it can easily cross into hurtful territory — even if you didn’t mean it that way.

Here are a few key points to keep in mind:

Impact matters more than intent – You might mean it as harmless fun, but if the other person feels embarrassed, excluded, or belittled, the joke has already missed the mark.
Power dynamics amplify harm – Jokes aimed at someone in a vulnerable position (socially, professionally, emotionally) can feel more like bullying than humor.
“I was only kidding” isn’t a fix – If you have to explain that it was a joke after the fact, it probably wasn’t as lighthearted as you thought.
A kinder alternative:

Use self-deprecating humor — making yourself the punchline shows humility and makes others feel safe laughing with you, not at you.
Keep jokes inclusive — focus on shared experiences or playful exaggerations that don’t single anyone out negatively.
Read the room — if someone seems uncomfortable, steer the humor elsewhere.
If you’d like, I can give you examples of playful, non-hurtful jokes that still get laughs without targeting anyone. Would you like me to do that?