40-year-old coworker repeatedly asks 25-year-old colleague for thousands in loans, turning the office into his personal cash machine with nonstop awkward money talk: ‘I'm not the only coworker he's requested this, It's making me feel extremely uneasy’

Author image for Etai Eshet
Etai Eshet • Editor
Apr 22, 2025 7:00 AM EDT

Some people see the workplace as a place for collaboration, innovation, and the occasional bland sheet cake for birthdays. Others approach the office like it is their own private cash dispensary, handing out withdrawal slips disguised as friendly conversation. 

In their world, every shared project is an opportunity for a loan request, and every team meeting holds the promise of a new venture in short-term coworker financing.

The coworker-for-cash system is powered by equal parts guilt and optimism, with just a dash of professional discomfort. It starts with a casual hint, then a plea for understanding, and finally a promise to pay the moment circumstances allow. The emotional energy required to dodge, deflect, and diplomatically decline these requests could power half the printers in the building.

But, you have to admit, this type of shamelessness is kind of admirable, while I'm over here overthinking how to ask my own brother for a ride to our parents', some of us are out there asking coworkers half their age for thousands in cash. And that, people, requires some nerve.

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  • The office can be many things, but it should never double as a low-interest loan agency for the persistently cash-strapped.

  • "Coworker keeps asking for money."

    "Coworker keeps asking for money"
    via Elnur

    The image does not depict the actual subjects of the story. Subjects are models.

  • Back at the end of January a coworker of mine (early 40sM) asked me (25F) for money. At first I was cautious but told him I could lend him some and made
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  • him sign a written contract saying he would need to pay me back by the end of March. He ended up requesting 2k... 2k!!!! And the pushover that I am agreed to it.
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  • When I reminded him of the deadline in mid-March, he told me he might take two more weeks to repay me. I wrote him an email telling him that if he
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  • Cheezburger Image 10496558848
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    The image does not depict the actual subjects of the story. Subjects are models.

  • doesn't pay me on time like he agreed I would file a complaint to a small claims court and escalate the matter to HR as well. I received the payment three days
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  • later I believe, the full 2k, coming from someone else than him. I didn't ask any questions, but it got me thinking...
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  • Then on two separate occasions he asked me if he could borrow 1k again and both times I gave excuses as to why I couldn't. It's making me feel extremely uneasy.
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  • Cheezburger Image 10496558336
    via petrdlouhy

    The image does not depict the actual subjects of the story. Subjects are models.

  • I've also learned that I'm not the only coworker he's requested this to three others were asked before me, but I'm not sure about the time frame.
    via khyplionna
  • Knitchick82 Two lessons here: 1: NEVER lend money that you don't mind losing.
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  • 2: NEVER lend money to, or sleep with coworkers. Both tend to end in anger and resentment.
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  • Tell him you're no longer lending money. If he asks again reiterate, and warn that further requests will need to involve HR. If it continues, involve HR.
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  • BurnerLibrary Moving forward, say, "Jared, I want to thank you for teaching me a very valuable life lesson. I've learned to not make personal loans. I'm sure you'll understand and stop asking."
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  • No excuses, ever. Don't et it trouble you to the point that the above comes out as exasperated,because it's really true.
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  • Wakemeup3000 No is a complete answer. You don't need to give an excuse on why just a 'No that won't work for me' and leave it at that. Your
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  • coworker is either bad with finances or has other issues. Neither of these are yours to solve.
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  • Zealousideallmage575 Not a coworker but my brother had a coworkers years before who asked me to borrow a large sum of money. I had just bought a condo, was early-ish
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  • 20s. I said no, it was so uncomfortable. A few months later his garage caught on fire with what he wanted to pay off inside.
    via Zealousideallmage575
  • RegisterLoose9918 Lending serious amounts of money is never a good idea between couples, family or coworkers. It just makes the hole environment toxic and hostile especially when the person taking the money eventually fails to pay it back in time or at all.
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  • Just be smart and say I don't think its a good idea. If someone is in financial trouble, there is a good chance they will not pay you back. It's literally why banks use your credit history to deem you fit for loans or not.
    via RegisterLoose9918
  • FilmAdorable1814 I think you need to tell HR regardless.
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  • Sea_Substance9163 Tell him "they" increased your school loan repayments by a ton, and you have no money and that you were hoping he could spot you some money. He will run away so fast.
    via Sea_Substance9163

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management boss workplace-stories hr toxic-workplace manager bosses work PTO managers supervisor workplace Horrible Bosses work-life balance
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