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85 Painfully Entitled Choosing Beggars Who Walk Among Us

85 Painfully Entitled Choosing Beggars Who Walk Among Us

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“Can you buy me a Gucci bag? It’s my birthday soon.” Imagine a stranger (or even a casual acquaintance) making a request like that. You’d probably stare at them for a second wondering if they were joking. Most of us wouldn’t dream of asking someone else to spend hundreds or even thousands of dollars on us, especially when we barely know each other. But every now and then, you come across people who seem to have a completely different understanding of what’s reasonable. They’ll ask for expensive gifts, huge favors, or freebies without the slightest hint of embarrassment.
And the strangest part? Some of them genuinely seem surprised when someone says no. From expecting strangers to pay their bills to asking for expensive items simply because they feel entitled to them, these requests can reach truly impressive levels of audacity. Thankfully, people on the receiving end aren't always keeping quiet. They’re sharing these encounters online, giving the rest of us a front-row seat to some spectacularly entitled behavior. Scroll down to see some of the wildest requests and try to keep a straight face.

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#1 I Was Giving Away A Free Dishwasher On Craigslist And Caught One In The Wild!

A text message showing an outrageous request for more free items with a free dishwasher, not understanding money.
Report
56points

#2 People Have No Shame

A text conversation showing an outrageous request to buy a $900 kettlebell set for $100.
45points

#3 People Have No Shame

A text conversation showing an outrageous request for gas money to pick up a microwave.
45points

In today’s world, with the cost of rent, groceries, bills, and pretty much everything else climbing, it’s perfectly understandable that people are looking for ways to save money. Maybe you compare prices before shopping, hunt for discounts, use coupons, or wait for a sale before making a purchase. There’s absolutely nothing wrong with being careful about where your money goes. In fact, being financially responsible can make a huge difference over time. But there’s a pretty big difference between being frugal and being downright cheap. Saving money means making thoughtful choices with your own spending. Being cheap, on the other hand, can sometimes mean expecting everyone else to pick up the tab.

#4 Asking For Food In A Local Fb Group

A text conversation showing outrageous requests for money instead of offered food for children.
43points

#5 Hmm

A screenshot of a text message conversation showing outrageous requests for a free dresser, highlighting people who don't understand how money works.
36points

#6 People Have No Shame

A text message exchange with an outrageous request about money, asking if a $2 price is negotiable.
31points

So, what exactly makes someone a cheapskate? Generally speaking, it’s someone who goes out of their way to avoid paying their fair share, even when they can afford to contribute. The problem is that their attempts to save money often end up costing someone else instead. As Yahoo Finance explains, being cheap is generally viewed negatively, while being frugal is about making smart and intentional financial decisions. A frugal person might skip an unnecessary purchase because they have a bigger goal in mind. A cheapskate might conveniently “forget” their wallet when the restaurant bill arrives. See the difference?

#7 Free Bed, Still Asked To Deliver It

A conversation about a free double bed, highlighting outrageous requests for delivery and how money works.
31points

#8 I Hate To Say This But…

A text message conversation about an outrageous request to pay only $100 for a stand mixer due to financial issues.
30points

#9 This Person Had 51 Followers

A micro-influencer asks for free art, displaying outrageous requests and a misunderstanding of how money works.
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26points

Etiquette expert and keynote speaker Thomas Farley, known as Mister Manners, put it rather neatly in a piece for CNBC. “A cheapskate is someone who is simply not paying their fair share,” he explained, pointing out that even a billionaire can be a cheapskate. According to Farley, the issue isn't necessarily how much money someone has sitting in the bank. It’s about deliberately choosing not to spend it when doing so leaves other people to cover the difference. In other words, being wealthy doesn't automatically make someone generous, and being on a budget doesn't make someone cheap. Sometimes, it all comes down to whether you're being considerate of the people around you.

#10 Free Game, Fast Attitude

An outrageous request from a YouTuber with 200 subs asking for a free game or payment for a good review. Doesn't understand money.
unknown
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25points

#11 Please Form An Orderly Line To Take This Dude In!

A social media post with an outrageous request about a registered offender looking for a room, not understanding how money works.
24points

#12 $2 For A 36 Minute Trip..in This Economy??? Lmao

A chat conversation with an outrageous request for free delivery of a mouse, even asking for $2.
23points

And here’s the thing: being frugal doesn't have to mean living a miserable life or refusing to spend money on anything fun. Amy Dacyczyn, author of The Tightwad Gazette, famously approached thrift from a completely different angle. The publication began in 1990 as a small black-and-white newsletter written from her farmhouse in Maine. Dacyczyn, who became known as the “Frugal Zealot,” wanted to show that families could live comfortably on a modest income while still reaching major financial goals, including buying a home and raising six children. The newsletter eventually attracted a huge following and was compiled into a book in 1998, becoming something of a bible for extreme thrifting and creative money-saving.

#13 Birthday Month, Champagne Taste

A social media post with an outrageous request for a free or cheap Marc Jacobs bag as a birthday gift, showing misunderstanding of how money works.
unknown
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23points

#14 Told Her No Politely The First Time

A chat showing outrageous requests from a buyer offering $150-200 for an $875 sewing machine, misunderstanding how money works.
22points

#15 Facebook Find.... Jesus

A social media post from a film community with an outrageous request for free labor for home renovations.
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22points

For Dacyczyn, frugality wasn't about constantly telling yourself “no” or feeling guilty every time you spent money. Instead, she treated it almost like a puzzle: How can you solve a problem without immediately throwing money at it? Her philosophy encouraged people to replace spending with creativity, time, effort, and a little resourcefulness. Leftover food could become tomorrow's lunch, an old item could be repaired instead of replaced, and an ordinary errand could be planned more efficiently. In that sense, being frugal can actually be surprisingly empowering. You're not simply avoiding spending; you're finding smarter ways to get what you need without unnecessarily reaching for your wallet.

#16 Woman Asks For Blue Prius In Buy Nothing Group

A post from a Buy Nothing group requesting a free hybrid car, showing outrageous requests about money.
22points

#17 Bride In One Of My Local Wedding Groups Looking For Vendors To Join An "Unpaid Collaboration"

A social media post with outrageous requests for unpaid wedding vendors to collaborate for portfolio building, misunderstanding how money works.
21points

#18 It's Just Not Going To Work

A chat exchange showing an outrageous request from a buyer who can't pick up a Samsung phone.
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21points

And sometimes, it's the tiny everyday habits that make the biggest difference. Canceling a streaming service you barely watch, turning the heating down by a degree or two, washing clothes in cold water, hanging them outside to dry, or unplugging appliances you're not using might not feel like major financial victories. Neither does repairing something instead of immediately buying a replacement. But when those little decisions become habits, they can add up over months and years. The same goes for planning meals, bringing lunch from home, buying secondhand, or simply waiting a day before making an impulse purchase. None of these choices will magically make you rich, but together they can leave noticeably more money in your pocket.

#19 Furnish My House & Deliver

An online ad showing an outrageous request for household goods to be delivered due to no vehicle.
unknown
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21points

#20 Trade Your Car For My Counterfeit Watch

A listing showing an outrageous request to trade a Rolex watch for a car, not understanding how money works.
19points
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