FAIL Blog - Work Life and Social Dilemmas - Employment, Life, Work, Culture - Cheezburger

employee job uber work travel expanses business trip Travel workplace company money Workplace - 46561541

Company refuses to reimburse employee for business travel expenses, claiming they didn't follow policy, leading employee to spend double on the next trip: ‘They paid up’

management workplace discussion employment issues boss workplace-stories hr coworkers colleague Horrible Bosses Workplace - 46561797

Two-person office forced to use a fancy phone system with hold music, so workers play the owner’s son-in-law’s terrible CD as muzak, and the requirement gets dropped as soon as a VP hears it

This father and his wife can afford to fund their daughter's college education thanks to a $3 million inheritance. However, the father will only pay for her chosen private-school tuition if she chooses to major in theater, art, or any other creative subject with “uncertain” employment.

Dad refuses to pay for daughter's college tuition if she chooses an arts degree, despite being able to easily thanks to a $3 million inheritance, daughter and wife disagree: 'She absolutely hated this'

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friends vacation time tired of it entitled people Holidays - 46558213

Friend gets tired of carrying his friend's suitcase for miles, so he asked them to hold it for 5 minutes, and they denied, then he snapped in anger towards them: 'Out of anger, I said, I’ll cancel the hotel reservation since it’s under my name"'

Content freelancer refuses to take client back after they tried to replace her with AI, then came back to offer 40% less than what they paid before: ‘They failed’

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boyfriend friends girlfriend game night toxic relationship Relationships - 46557701

Gilfriend gets upset at boyfriend for letting his friend come over for "boardgame night" with his new girlfriend, and she thinks that is breaking a boundary: 'This is the first time it happened, so I didn't know that we have this particular "rule"'

schedule boss bad boss meetings zoom meeting Horrible Bosses bad bosses work schedule Bad Bosses - 46565637

Boss reschedules weekly 9:35 AM meeting to 9:32 AM, berates employee at 9:33 when he's a minute late: 'I would have assumed it was a mistake and still joined at 9:35.'

humor salary hourly manager job work coworkers co-workers employees career comedy supervisor workplace funny Workplace - 46555653

'It all started when the internet...': Pour a dash of these laughs into your morning coffee for extra energy (August 25, 2026)

Elna McHilderson

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New issues arising with the AI revolution. I get it; it’s a terrible position to be in. Sometimes we reveal things accidentally that compromise other people’s work.

Employee accidentally exposes coworkers who were using AI to respond to emails and confidently providing wrong answers: ‘There's definitely a "well look who's the favorite now" vibe from a couple people’

We're all searching for that job that pays really well, takes little of our time, and doesn't require that much effort, but still somehow leaves us feeling that our purpose in life is fulfilled. This job exists almost as a fantasy. And like being in an alternative “indie” rock band in the 00s or 2010s, you kinda had to be born into it.

20+ Jobs that sound fake but actually pay really well for those considering an out-of-left-field career change: 'Bear removal expert'

A male supervisor standing over a female employee working on a laptop.

Employee develops crush on boss, gets fired for not acting on it: 'I just wanted to do the right thing'

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Questioning Life Paths In Your Thirties There comes a time in everyone’s life when we can’t help but question the path society expects us to follow. Sometimes we question it and realize

'I’m sure plenty of people would find that pathetic, but I honestly don’t care’: 31-year-old man realizes the traditional life he envisioned isn’t really what he wants, and there’s no point in buying a house just for the sake of building equity

family drama motherhood niece babysitting Family - 46557445

Sister doesn’t want to babysit her baby niece as her daughter has just started daycare and now she has 6 hours to herself: ‘I just have zero interest in watching anyone else’s children no matter the circumstances.’

boss marriage baby cheating husband wife married life cheating wife husband cheating ex wife Friends - 46556165

Wife cheats on her husband with her boss, gets divorced and married to her boss, now she thinks her husband is cheating on her and gets mad at her friend for not supporting her

Giuliana Tiscioni

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antiwork toxic-workplace job bosses work coworkers content creator working influencer toxic-boss ai workplace bad bosses Workplace - 46551813

Brands replace content creators with AI, when numbers tank they try to get creators back with lower pay: 'They are back in my DMs offering 40% less than what they paid me before'

Employees are forced to pay $80 a month in order to park at the office they were forced to return to in a return to office mandate

Company forces fully remote employees to return to the office after 4 years of successful remote work, begins charging them $80 a month to park outside the building: 'I'm seriously considering just quitting over this'

A person in an orange coverall and a black hat

Manager cuts all employees hours from 30-40 hours per week to 10-15 hours per week, leaving facility barely functional: 'The AC was stuck at 82 degrees during the 95+ degree heatwave.'

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Close-up of a server putting a salad on a table that has several drinks glasses, and a couple sat there.

Man demands restaurant server leave him alone on first date, misses out on second date because of lack of service: 'My job is to guide people without being overbearing'

Those dreadful family gatherings where everyone is suddenly interested in your love life I don’t know if it’s just me, but I’m always on this side of family gatherings, and I have to say It’s genuinely soul-crushing, and it’s something that has to stop. It’s enough to have an entire society telling you what you should

‘The pretty ones get picked first at the market’: Family makes nasty remarks to 22-year-old because she isn’t married yet