5 Jokes About Bad Decisions

Double Meaning Jokes

Updated on: Mar 15 2025

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The Gambler's Dilemma

Trying to win it all, but losing everything.
My financial advisor told me I should diversify my portfolio. So, now I invest in both bad stocks and bad poker hands.

The Procrastinator's Plight

Putting things off until it's too late.
I finally decided to procrastinate procrastination. It turns out, I'm really good at it.

The Online Shopper's Regret

Clicking 'Buy Now' and instantly regretting it.
I'm not saying I have a shopping problem, but my mailman and I are on a first-name basis. He calls me "The Regret Express.

The Relationship Strategist

Thinking you know everything about relationships but realizing you don't.
I asked my significant other what the secret to a happy marriage is. They said, "Not asking too many questions." That's not a good sign.

The DIY Enthusiast's Nightmare

Believing you can fix anything, but making it worse.
I'm all for DIY, but apparently, "Do It Yourself" doesn't mean "Destroy It Yourself.

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