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An overly confident young employee strolls into a meeting to ask his boss for a 50% raise.

Gen Z employee demands a 50% raise after 1 year of work, requests meeting with CEO after his manager says no: 'He informed me that he deserves a $41K bump.'

An older and younger woman sit together having coffee, discussing something on the laptop in front of them

Mom gifts 30-year-old daughter $400k rental property in Sacramento, boyfriend protests that it's in her name only: 'He wants me to turn down the gift'

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Movers berates customer for taking more than 20 minutes to tip for their services: 'Demanding a tip is a great way to ensure you don't get one.'

The living room of an expensive New York City apartment, complete with crown molding and a dazzling chandelier

Girlfriend requires a $ 15K-a-month, 3-bedroom NYC apartment with outdoor space and crown molding, much to her boyfriend's dismay: 'I pay for 70% of everything, including rent.'

A woman smiles while walking through a college campus, holding a shoulder bag and a laptop

Parents put $300k in each daughter's college fund, 22-year-old protests when they want to take $100k from her fund and give it to 18-year-old: 'Her dream school is very expensive'

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A group of young cheerful friends relaxing indoors

Scammer charges roommate $1000 per month after telling him the rent is $1600, roommate discovers the rent is actually $1000: 'The landlord says we're short on rent because he only gives the landlord $800 a month.'

A female hospitality worker smiles while holding a clipboard behind a counter with a coffee machine behind her

Customer gives restaurant worker $5000 tip, manager demands they split it between every employee: 'Am I selfish to want to object?'

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Stepdad refuses to pay for his stepchild's college at the expense of his kid's college funds: 'My wife says it’s not fair that my child will have enough money for 4 years at college and her child will not.'

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Job applicant ends Zoom call after recruiter calls their salary expectations 'cute': 'We expect 50-hour weeks, but the base rate is non-negotiable'

A young woman graduating with a degree in theater who has no idea how difficult it's going to be to pay off her student loans.

25-year-old daughter asks mom to pay off all her student loan debt for her Theater degree with her $200K inheritance, but mom refuses: 'I knew she wasn't the next Broadway actor.'

Middle-aged dad asks his teenage son for money, instead of going out and getting himself a job.

16-year-old refuses to give his unemployed 53-year-old father $200 a month for gas money: 'If you weren’t this bad off before I got a job, why are you now?'

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A man and a woman lean over a balcony on a tropical building, with the man pointing to something

Vacationer agrees to allow girlfriend's friends to join them on holiday, changes mind when they demand he pays $2800 each in travel costs: 'They are calling me a miser'

Son refuses to pull Mom out of assisted living so he can afford helping in-laws with financial situation: ‘They want me to move my mom into our house’

Son refuses to pull Mom out of assisted living so he can afford helping in-laws with financial situation: ‘They want me to move my mom into our house to save costs’

An older couple sits at a table together, looking at something the man is pointing to on his cell phone

Son-in-law refuses parental offer of $150k house down payment that comes with the condition of creating a postnup: 'My parents saw my aunt go through something similar'

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Man refuses to accept $150k from his in-laws to help pay for a downpayment because they demand a post-nup in exchange, sparks debate about family gifts: 'Money comes with implied strings'

Jesse Kessenheimer

A middle-aged husband is contemplating whether he and his wife can afford to retire on $5M in a few short years

47-year-old husband thinks he won't be able to afford to retire on $5 million in 7-10 years: 'If we can’t live on $200k a year, then we have a spending problem.'