Employee books $623 flight for boss on his personal credit card after the company card was declined, boss never pays employee back: 'I got scammed by my own boss'

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Ben Weiss • Writer and Editor
Nov 16, 2025 2:00 PM EST

Imagine having to shell out over $600 to your boss so he can rebook his flight, only for him to refuse to pay you back.

Yes, for this unfortunate employee, he had to deal with the strange reality of getting scammed by the person who signs his paychecks. It all started when the employee's boss called him in a panic at the airport on his way back from a business trip. It turns out that for whatever reason, the company's credit card was declined, and the boss was unable to rebook his flight. Why he couldn't use his own credit card is beyond us!

Regardless, the author felt pressured to get him on the next flight back, so he took the plunge and used his personal credit card. Of course, at the time, his boss promised to pay him back. That was now months ago.

It's not like this employee has been too afraid to speak up for himself. In fact, he has brought up the fact that his boss owes him money time and time again. With each occurrence, the boss managed to think of a different excuse to avoid fulfilling his promise. Keep scrolling below for the full story and for the best reactions from several members of this online community.

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  • A man speaks on the phone while working on his laptop in an office.
    via Vitaly Gariev

    Image is representative only and does not depict the actual subjects of the story.

  • Thankfully, the author has acknowledged that he is already looking for better opportunities elsewhere, but not until after he collects that $600! It's not even that his boss hadn't been paid recently, either. He was simply withholding the money under the guise of being too busy to care!

  • "My boss made me pay for his $600 flight and it's been 2 months with no reimbursement"

    My boss called me from the airport in September saying his card was declined and asked me to book his $623 flight on my personal card. Said he'd pay me back as soon as he landed
    via Affectionate_Sir2440
  • That was September 12th. It's now November 13th I've asked him SIX times and keep getting excuses
    via Affectionate_Sir2440
  • • I'll Venmo you this week (never did) • Send me the receipt again (I did nothing happened) . • I'm waiting for my expense report to process (why does that matter?) • Last week: You're being really pushy about this
    via Affectionate_Sir2440
  • I'M BEING PUSHY??? IT'S $623 AND IT'S BEEN 2 MONTHS I make around $52k a year. This is basically my entire discretionary budget for a month.
    via Affectionate_Sir2440
  • The worst part is that I saw him expense it to the company. He already got reimbursed. He has the money. He's just not paying me back
    via Affectionate_Sir2440
  • Do I go to HR? Small claims court? Just accept I got scammed by my own boss I feel so stupid but he's my BOSS and he was in a panic and I was trying to help (and I didnt want to get fired)
    via Affectionate_Sir2440
  • G... 17h ago Edited 17h ago Straight to HR. They will be very interested to know that your boss is violating the company expense policy. There is literally no way you were supposed to pay for his ticket. He is probably faking his expense reports too.
    via Affectionate_Sir2440
  • Just before you go to HR, submit an expense report of your own with your receipt and the label "Boss's airplane ticket". That will get the finance department involved as well.
    via Affectionate_Sir2440
  • A young businessman holds his phone and jacket in one hand while carrying a suitcase in the other at the airport.
    via Unsplash+ (Getty Images)

    Image is representative only and does not depict the actual subjects of the story.

  • savoryannuity6162 17h ago . Go to HR. HR doesn't care? Simple, I'd document everything you have and go straight to small claims court. You don't need a lawyer for $623 and he's clearly just hoping you'll give up
    via Affectionate_Sir2440
  • YesterShill • 17h ago He was reimbursed for an expense he did not incur. This is a corp issue where HR needs to be involved. They should have simply reimbursed you directly in the first place.
    via Affectionate_Sir2440
  • Chicken65 · 17h ago Your boss has some pretty steep personal finance issues. 100% tell HR, don't warn him. A superior asking a subordinate for money is a big no no.
    via Affectionate_Sir2440
  • . Gloomy-Conferen... 17h ago File your own expense report with the receipt and title it "bosses name - flight- date" when they hopefully realise they've already paid him out for it, it'll raise questions and hopefully get you the right result
    via Affectionate_Sir2440
  • shontsu 17h ago Sorry, but why on earth would you do that? Yes, go to HR, but...d. What kind of business travel requires someone to turn up at the airport and buy a ticket at the counter on their card? This is shady as f
    via Affectionate_Sir2440
  • ooferfeesh97.16h ago Ask him for the $800 he owes you via text, when he corrects you, he just made a paper trail.
    via Affectionate_Sir2440

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workplace-stories employee work stories toxic-workplace job work flight Horrible Bosses company money toxic-work-environment
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