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I walked past a homeless guy with a sign that read

Posted on August 30, 2025 by Joke Poo

“One day this could be you.” I put my money back in my pocket, just in case he is right .

Okay, here’s my attempt:

Joke Poo: The Motivational Speaker

I listened to a motivational speaker who said, “Visualize success, and it will be yours!” I immediately pictured winning the lottery. Then, I went and bought a lottery ticket, just in case he was right.

Alright, let’s break down this joke and then build something funny on top of it.

Joke Dissection:

  • Setup: The joke begins with a relatable scenario: encountering a homeless person holding a sign. The sign’s message is provocative: “One day this could be you.”
  • Punchline: The humor lies in the character’s unexpected reaction: instead of feeling pity or empathy (the expected responses), they interpret the sign as a warning and hoard their money.
  • Core Elements:
    • Homelessness: A serious social issue.
    • Guilt/Empathy: The expected emotional response.
    • Self-Preservation/Paranoia: The comedic twist, subverting expectations.
    • Financial Security (or lack thereof): The implied fear of poverty.

Comedic Enrichment: Combining Factual Tidbits with Humor

Let’s leverage some facts related to homelessness and combine them with the joke’s spirit of paranoid self-preservation:

New Joke:

I saw a homeless guy holding a sign that read, “One day this could be you.” I almost gave him money, then I remembered: the average life expectancy for a homeless person is 12 years shorter than someone with stable housing. Now, I’m trying to decide if I should give him money to boost his spirits, or aggressively invest in a condo to ensure I live long enough to avoid the problem entirely.

Witty Observation:

That homeless guy’s sign was a real wake-up call. Turns out, homelessness can age you faster than smoking and filing your taxes late. I’m thinking of starting a GoFundMe to buy us both some retinol. You know, for preventative reasons.

Amusing ‘Did You Know?’

Did you know the saying “sleeping rough” came about because it was commonly believed during the 1800s that straw beddings hosted scabies mites and fleas, so people who had to sleep in a stable chose to sleep on the rough straw floor rather than a straw bedding?

Why this works:

  • The “new joke” builds on the original’s premise by adding a layer of absurd logic based on a factual statistic. The humor comes from the extreme and selfish conclusion the character draws.
  • The “witty observation” continues the theme of avoiding homelessness at all costs. It links the fear of homelessness to vanity (aging) and responsibility (taxes), creating a comical juxtaposition.
  • The “Amusing ‘Did You Know?'” is interesting and unexpected, and serves as an introduction to a discussion of the conditions and issues of homelessness.

The goal is to use the original joke as a springboard to explore the same themes (fear, money, self-preservation) in new and unexpected ways, ideally enhanced by a dose of reality or absurdity.

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