My uncle in Tulsa bet me $20 I couldn't make a good pun without the word "udder," and he was right

Alice Harris · 2026-10-09T08:55:04.310926+00:00

Last month my uncle Ray bet me $20 at a family cookout in Tulsa that I could not write a clean dairy pun without leaning on that one cow word. I took the bet and spent the whole week filling a notebook with lines about milk and moo and lactose, and every single one flopped when I tried it on my kids. My 9 year old just stared at me and said "dad that is not even a joke." Ray finally looked at my list and said the problem is that the punchline has to land somewhere new, not on the same old farming bit everyone has heard. I paid him the 20 and kept the notebook. So what is your go to move when a pun keeps landing flat, do you toss it or keep poking at the setup?

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My uncle in Tulsa bet me $20 I couldn't make a good pun without the word "udder," and he was right | Dad Joke Workshop - Hub Chatter