11 Reddit Money Messes That Have Us Guarding Our Wallets — & Saving up for Disasters

If there’s one thing the “Am I The A-hole” (AITA) subreddit proves (besides that people are, ya know, a-holes), it’s that money drama definitely grows on trees. Family trees, specifically. We see financial feuds all the time (like, all the time). It’s everywhere, because beyond making the world go round, money makes people downright vicious.

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And as far as we can tell, these aren’t stories of people who are truly strapped for cash. People who are living paycheck-to-paycheck and are trying to put food on the table. They’re just greedy, stingy, clueless, or utterly uncompassionate.

We wish we weren’t here telling you about a mother-in-law who was a legitimate thief, a dad who tried to steal his daughter’s inheritance, or a mom who wanted her daughter to pay “market value” rent to live at home. We wish we weren’t, but do you remember that first thing Reddit proves? A whole lot of people are a-holes. And they’ll do a whole lot to take (or keep) some Benjamins.

And so let’s take a walk down a drama-filled memory lane that will hopefully remind you to keep your money close, your expectations clear, your relationships in mind, and your hands off everything in someone else’s house. Because if you remember the old cliché, money can’t buy happiness — but it can certainly cost you.

  • Major PSA

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    One AITA post from June 2023 seems to top the rest, and it’s acted as a PSA for people to change their bank pins and passwords frequently.

    A man joined Reddit to talk about his “not-yet stepmother” and her desire to have a big wedding. She has asked her “not-yet stepkids” to help pay for said wedding, and the original poster (OP) wass “super annoyed” by this. When he refused to contribute, she “flipped out” and took matters into her own hands.

    “Since I had a good relationship with my father, he had access to one account, [and] she simply took [money],” he said. “It wasn’t a significant amount, but when she refused to return the money, I threatened to report her to the police for theft.”

    “AS HE SHOULD,” Reddit yelled in unison. But for some mind-boggling reason, thinks he is the a-hole (AH). Read the full unbelievable story here … and remember to change your passwords, pronto.

  • A ‘Leeching’ MIL

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    A lot of adults support their parents or other family members financially, and the assumption is that it is done in good faith. But you know what they say about assumptions. One woman joined the AITA subreddit to talk about her mother-in-law, who frequently asked her husband for thousands of dollars.

    He has disposable income and was happy to help. But the MIL’s requests didn’t make sense to this woman since her FIL is seemingly successful. So when this MIL asked for $15K, OP asked her FIL if their finances were OK. He was shocked to learn about the requests — ultimately realizing she was stealing from him too.

    The family is now in shambles and the “lying and leaching” MIL gave an excuse that Reddit thinks is total BS. Read the full story, and where they think the cash really went, here.

  • You Break It, You Buy It

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    One uncle posted on Easter 2023 to talk about how his niece and nephew wouldn’t leave with only Peeps in their baskets — they would also be getting a bill for $1.5 thousand dollars. And Reddit is actually on his side! The 12- and 14-year-old menaces had broken into their aunt’s makeup collection and caused some major destruction. Let’s repeat that: not toddlers. Twelve and fourteen.

    “They had dug into her eyeshadow palettes with her brushes and poured out her foundations into them and a bunch of her compacts were in the sink soaked in water,” OP wrote.

    He and his wife tallied the damage to her $4K collection, and wrote his brother and sister-in-law a bill for what was destroyed. As you may have guessed, they put up a fight and refused to pay. And (as per usual) it’s probably because of the patriarchy.

    “If the kids came into your home and destroyed a $1500 painting they would be expected to pay for it, right?” one Redditor said. “Makeup is expensive, and it’s unfortunate that they are in this position, but it is what it is. You break it you buy it. You’re not running a charity or a funhouse for their kids. This is a big learning experience for your bro and his kids; don’t touch other people’s things without express permission.”

    Read the whole makeup mess here.

  • Same Gist

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    A similar incident occurred with a man whose niece and nephew ruined his wife’s art supplies. He asked his brother-in-law for $375 to replace the markers and other damaged goods. It’s a smaller bill, but Reddit seems even more fired up about this one. And honestly, their logic (found here) has us fuming too.

  • A Wrongful Venmo Request

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    Reddit spotted a whole lot of red flags in a post that the writer would have preferred to be spotless. The stepmom in question suffers from Obsessive Compulsive Disorder and pays for a cleaning service to keep her house tidy. One day, after a cleaning, her stepdaughter brought friends over and “ruined” the house. And so OP Venmo-requested her the price of the cleaning service.

    OP explained that the friends didn’t take their shoes off, leaving footprints “all around the house,” and left “crumbles on the counter” after making pizza from scratch.

    Um. That doesn’t sound like “ruined” to us, and it didn’t sound like “ruined” to Reddit either. Users were waiting to hear about the horrible mess that was worth “ruining” a relationship over. When they didn’t get it, they came up with several solutions (read the whole story here) and ultimately urged OP to consider investing in her mental health instead of a high-end housekeeper.

    “I have OCD,” one Redditor said. “I’m genuinely baffled that OP felt it was anything other than manipulative to refer to footprints and CRUMBS as DAMAGE … I thought this was going to be about some house party where furniture was destroyed and items were stolen. OP should consider therapy.”


  • Birthday Party Prices

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    Let’s be honest like this mom and admit that kids’ birthday parties are a drain and a drag. And do you know what doesn’t make them any better? You guessed it — drama!

    One mom experiences this annually because her daughter and niece were born 10 days apart. Thus, her sister-in-law has always pushed for a “shared” birthday party. Which would be sort of fine (though attention-loving kids might disagree) if the adults shared the bill, but you know where this is going.

    The OP’s brother and SIL never help with the costs, and so this year OP said enough is enough. It didn’t matter that “things were tight” for her brother and SIL; this year she was throwing a solo birthday party for her daughter. Everything was fine and dandy at the Formula 1-themed birthday party (how cool is that?!) until OP brought out the cake. SIL asked if this was “the girls’ cake” and OP said no, it was for her daughter since it was her [Formula 1-themed!!!] birthday party.

    “Now my daughter isn’t going to have any kind of celebration for her birthday this year because you and your husband are so selfish,” SIL said before “making a huge scene” by storming out of the kitchen and yelling to her family to say it’s time to leave.

    Reddit unanimously agreed that OP wasn’t the a-hole — and went above and beyond by sharing so many great ideas for what parents can do when things are tight (that don’t involve picking fights with family). Read the full list here. 

  • Wedding Woes

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    You saw this coming, right?! Because not a day goes by that there isn’t wedding drama on Reddit. This one actually has the internet divided, which doesn’t happen as often as you’d think on AITA.

    One father of the bride said he would give the happy couple an undisclosed amount of money for the wedding. When they opted out of a venue-wedding and decided to elope, the bride asked for that money to fund a month-long honeymoon instead.

    Reddit isn’t quite sure if that’s reasonable or ridiculous and for what reasons, so we’ll let you decide. Read the full debacle here.

  • Saying No To A Nanny

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    Finances are serious business (duh!), so we’re always surprised to see posts that have Redditors saying, “It’s not a big deal.” One woman on Reddit has a thoughtful nanny, Tessa, who is actually paid by the state because OP’s daughter Ruby has autism.

    Ruby is a big reader, and Tessa will buy her books when she’s out thrift shopping. Ruby then pays her back with her allowance. It’s all very thoughtful. One day, Tessa told Ruby that she found some books she might like. She ended up spending $50 on 35 books. Ruby didn’t know it would cost that much and didn’t have that kind of money. OP then refused to cover the costs since she didn’t approve this purchase.

    Reddit said this is really straightforward (read their full thoughts here): Just hand over the $50 and be done with it.

    “Sometimes it’s better to salvage an important relationship than to be right,” a comment with 33.4k likes said. “Pay for the books. Let Tessa know that you can’t do so in the future, though, without talking about it. Tell her how much you appreciate her thoughtfulness, now and always.”

  • Utterly Horrifying

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    One teen on Reddit tragically lost her mother a year before she posted on AITA. Her mom’s money and house were left to her, and she plans to move there after she finishes college. But her father and stepmother were pressuring her to hand over the house and the money, and we couldn’t believe what we were reading. Can you imagine your mom dies and than your dad tries to manipulate you into giving away your inheritance? As we said when writing about the full story (that only gets more intense), this dad is “a top-level piece of garbage.”

  • To Pay Or Not To Pay

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    Paying grandparents for babysitting seems to be a touchy subject. As we said when writing about a particular situation in April 2023, we’ve seen posts on the subject go viral every six months or so. In Oct. 2021, one woman on the “Am I The A-hole?” subreddit couldn’t believe her retired parents wouldn’t babysit her children after she got a promotion. In April 2022, a grandma who worked full-time refused to babysit her grandchild on her days off and got a whole lot of backlash from her daughter. And in Dec. 2022, a mom just needed a moment to vent about how disheartening it is that neither her parents nor her in-laws will lend a hand.

    But in this situation, a mom joined to say it “boggles her mind” that some grandparents expect to be paid. She then shared her totally bizarre reasoning.

    “To me, [a grandparent asking to be paid for babysitting] is no different than a wife expecting her husband to give her money every time they have sex, just because prostitutes are paid for the same job.”

    Um … what?! Redditors mentioned how weird that comparison was before dividing themselves into Team Freebie and Team Invoice — and writing some really compelling comments.

  • Market-Average Markup

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    One mom is paying the price for asking her daughter to pay rent, and it’s going to come back and bite this AITA user in the … ya know. TLDR: Her adult daughter was in a tricky situation and needed to live with her for “6 months tops.” Instead of welcoming her with wide-open arms, she effectively locked her out, forcing her to move into a 2-bedroom apartment with SEVEN people.

    “She’s an adult now, and she needs to learn to take care of herself, not relying on handouts from her parents,” she said. “She offered to pay rent, but we would only do that if she agreed to pay the market average plus her share of utilities, which would mean she couldn’t save up like she wants to.”

    Market. Average. Are you actually kidding me, Mom?! Both Reddit and Twitter had a lot to say about this cold-hearted move. Like, a lot.

    “I hope OP enjoys the retirement home when they hit that age and might need their daughter to help out. Because unless you are willing to pay the market rate to her I don’t think she’ll help out, cuz you know, you need to learn to be an adult then too. Don’t come looking for hand outs.” 



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