10 A 40 Year Old Cowboy Jokes

Observational Jokes

Updated on: Jun 18 2025

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You know you're getting older when a 40-year-old cowboy starts trading in his lasso for a riding mower and his trusty steed for a John Deere.
It's funny how a 40-year-old cowboy still rocks that rugged look, but you know he's secretly into those scented candles and aromatherapy.
You ever notice how a 40-year-old cowboy is just a guy desperately holding onto a midlife crisis with spurs?
I saw a 40-year-old cowboy trying to fit into skinny jeans. Let's just say the only thing that was roped in was his sense of dignity.
Ever notice how a 40-year-old cowboy's belt buckle keeps getting bigger, but his tolerance for spicy food keeps getting smaller? It's like he's compensating for lost heat with belt bling.
I saw a 40-year-old cowboy the other day, and I couldn't tell if he was wrangling cattle or just trying to remember where he left his reading glasses.
A 40-year-old cowboy at a yoga class is like a fish out of water, or should I say, a stallion in a stable full of goats.
I asked a 40-year-old cowboy how he keeps up with the times. He said, "Well, partner, I swapped out my horse for a pickup truck, but I still can't figure out these dang smartphones.
You can tell a 40-year-old cowboy's age by counting the number of "back in my day" stories that start with "Well, when I was ridin' the trails...
A 40-year-old cowboy's idea of a wild night is switching from regular to decaf after 6 PM.

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