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We’ve never had it easier when it comes to buying and selling secondhand stuff. That unworn top gathering dust in your closet? Someone out there wants it. Looking for a cute bag without the boutique price tag? A few clicks online and it’s yours. At least, that’s the theory.

In practice, anything involving other humans is destined to go sideways. Which is why both buyers and sellers regularly find themselves in increasingly unhinged DM exchanges that would make Tarantino dialogue look reasonable.

The Instagram account DM Drama captures these gloriously painful conversations in all their chaotic glory. We’ve rounded up the best of them below.

#1

Chat conversation revealing a buyer and seller dispute with fake car crash proof in buying and selling things gone wrong.

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The ferocity in some of these DMs makes you wonder if people think they’re wrestling over the last discounted flatscreen on Black Friday instead of a used sundress.

The haggling, the indignation, the dramatic standoffs over a $15 shirt would make a medieval marketplace merchant proud. It’s absurd, and yet completely entertaining to witness strangers go to war over secondhand clothes.

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    #2

    Skeleton modeling a purple Eldon cashmere scarf for a funny buying and selling things fail example.

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    #3

    Buyer and seller confused over item details in a frustrating buying and selling conversation gone wrong.

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    The word “thrift” itself dates back to 1300s Middle English, meaning “fact or condition of thriving” and “prosperity, savings.” The concept grew not from desperation but from using resources carefully to prosper.

    According to Dennita Sewell, professor of practice and fashion expert at Arizona State University’s Herberger Institute for Design and the Arts, “The secondhand trade is one of the oldest forms of clothing for the common man. Every era it comes to provides a reflection of the ideals of that period.”

    #4

    Parcel full of baked beans instead of a Reform UK T-shirt showing buying and selling things that did not go well.

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    #5

    Buyer showing a Halloween costume with green face paint and a brown waistcoat after a buying and selling exchange.

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    This trade has ancient roots. Piles of used clothes appeared in market squares across Europe as early as the 1300s. As society modernized, secondhand clothing operated as a bartering system, serving low income communities during the Middle Ages. The practice was practical and unremarkable for centuries.

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    The Industrial Revolution changed everything. Mass production made clothing more affordable and disposable, which sounds positive until you consider what it did to perceptions of secondhand goods.

    As Sewell told The State Press, economic divides widened and classism became more rampant. Secondhand consumption became stigmatized, particularly targeting immigrant communities and fostering xenophobia.

    #6

    Customer disputes parcel delivery with photos and messages in a buying and selling transaction gone wrong.

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    #7

    Chat conversation showing a buyer and seller interaction where buying and selling things did not go well.

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    #8

    Text message conversation showing a buying and selling misunderstanding involving a returned Chelsea shirt request.

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    The modern idea of thrifting as we know it emerged between the mid 1800s and early 1900s with organizations like the Salvation Army and Goodwill.

    “The popularity of thrifting has come and gone throughout the years,” Sewell explained. “Sometimes it represented something greater than itself, other times it represented staying in the past. It all has to do with the culture of the time.”

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    The early 1900s carried that unjust stigma until the Great Depression hit and consumer demand for secondhand clothes exceeded supply. Suddenly, thrifting wasn’t shameful anymore.

    #9

    Chat conversation showing buyer worried about no reviews when buying Korn adidas Campus shoes, a buying and selling fail example.

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    #10

    Chat conversation showing confusion over clothing size in a buying and selling transaction gone wrong.

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    #11

    Text message exchange showing a failed buying and selling negotiation with an unfriendly response included.

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    The later half of the 20th century proved more open minded. The 1970s in particular sparked a new wave of thrifting tied directly to counterculture movements.

    “The 1970s was all about expressing individuality to the youth counterculture,” Sewell said. “Thrifting represented freedom for them. The hippie movement allowed secondhand clothing to have more value and become chic again.”

    #12

    Man wearing a knitted hat in a mirror selfie, reacting to a failed buying and selling item experience online.

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    #13

    Conversation showing a confusing buying and selling exchange with an unexpected extra item and package mystery.

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    #14

    Chat conversation showing a buyer doubting seller’s excuse and proof of injury in a buying and selling situation.

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    Today, the secondhand clothing market is massive. According to ThredUp’s 2025 Resale Report, the global secondhand apparel market is expected to reach $367 billion by 2029, more than double its size from 2023.

    Online platforms have supercharged this growth, making it easier than ever to buy and sell used clothes from your couch.

    Take Vinted, one of Europe’s largest secondhand fashion platforms. The company has 80 million registered members across 18 countries as of 2023. That’s a staggering number of people actively buying, selling, and browsing used clothing.

    In the UK alone, one in three people bought secondhand fashion in 2023, a trend driven largely by younger shoppers.

    #15

    A hand holding a plastic water bottle wrapped in plastic wrap containing a pair of eyeglasses, illustrating buying and selling fails.

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    #16

    Buyer and seller chat about delay with a finger stuck in a lemonade can before order cancellation in buying and selling fails.

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    #17

    Chat conversation showing a seller canceling an order with an unusual personal reason in buying and selling fails.

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    The business model behind these platforms is straightforward but effective. Sellers list items, set their own prices, and ship directly to buyers. The platforms typically take a small commission or service fee.

    Vinted operates slightly differently by charging buyers a protection fee instead of taking commission from sellers, while Depop and Poshmark take a percentage of each sale. This peer-to-peer model eliminates the middleman of traditional retail.

    #18

    Chat conversation about buying and selling mishap where buyer got trapped for hours needing rescue and causing delays.

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    #19

    Chat conversation showing a confusing exchange about shipping costs, highlighting buying and selling things not going well.

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    #20

    Conversation about buying and selling 7 David Walliams books with payment and delivery issues shown.

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    What’s driving this boom isn’t just affordability. A McKinsey report on fashion found that sustainability concerns are increasingly influencing purchase decisions, particularly among younger, urban consumers.

    The fashion industry is one of the world’s biggest polluters, and buying secondhand is one tangible way people can reduce their environmental impact. Fast fashion’s overproduction has created mountains of waste, and secondhand markets help extend the life of garments that might otherwise end up in landfills.

    #21

    Message exchange over a Shein crop top sale showing buyer-seller communication problems and misunderstandings in buying and selling.

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    #22

    Buyer and seller dispute over undisclosed writing in a book, highlighting times buying and selling things did not go well.

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    #23

    Conversation showing a buying and selling dispute over delayed shipping of Prada sunglasses turning rude and confrontational.

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    But beneath all the environmental virtue and economic sense, there’s something delightfully chaotic about the human element. The platforms are smooth, the algorithms are smart, but the actual interactions between buyers and sellers remain wonderfully, messily human.

    Which brings us back to those DMs, where someone’s offering $3 for a vintage leather jacket and acting personally victimized when it gets declined.

    #24

    Chat conversation showing awkward buying and selling attempt on a shopping app with unwanted random messages.

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    #25

    Screenshot of a buyer informing delay in selling on Vinted due to personal issues, illustrating buying and selling problems.

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    #26

    Text conversation showing a buying and selling dispute with the seller canceling an order for rude reasons.

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    #27

    Buyer and seller in a messaging exchange with delays and misunderstandings during an online buying and selling transaction.

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    #28

    Haunted ceramic clown for sale with spooky history, showing unusual events after buying in a buying and selling fail story.

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    #29

    Text message conversation with humorous confusion, illustrating times buying and selling things did not go well.

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    #30

    Screenshot of a buying and selling conversation about a damaged ASOS top and buyer complaints with delivery issues.

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    #31

    Conversation showing failed buying and selling communication about delayed parcel shipment and cancellation request.

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    #32

    Conversation on a resale app showing a huge price gap in buying and selling things that did not go well.

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    #33

    Chat conversation showing a buyer requesting proof of delivery, followed by a humorous unexpected delivery photo.

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    #34

    Rare Baby Beanie Bear listed for £50,000 with tags, buyer questions price in a buying and selling things fail.

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    #35

    Chat conversation showing a buying and selling situation that did not go well with a canceled purchase.

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    #36

    Text message conversation about buying a vintage jacket with unexpected hair in pockets, illustrating buying and selling fails.

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    #37

    Text messages about a buyer claiming swapped shoes in a parcel, showing Adidas shoes instead of Prada, a buying and selling fail.

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    #38

    Chat conversation about buying Ugg shoes with sarcastic and dismissive replies showing buying and selling things did not go well.

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    #39

    Text message exchange showing confusion and frustration, illustrating times buying and selling things did not go well.

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    #40

    Buyer complaining about greasy KFC bag used for packaging a top, highlighting a buying and selling fail scenario.

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    #41

    Chat conversation showing a buyer complaining about Gymshark trousers with a fake stain in a buying and selling fail.

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    #42

    Screenshot of a buying and selling conversation about clothing size and fit, illustrating a buying and selling fail.

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    #43

    Bizarre homemade cake listing with distorted face and misshapen fingers, showing buying and selling things fail humor.

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    #44

    Conversation showing a failed buying and selling transaction dispute over a Burberry shirt on a resale platform.

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    #45

    Screenshot of a buyer-seller dispute showing damaged clothing and complaints about buying and selling things not going well.

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    #46

    Chat conversation showing buying and selling fails with damaged parcels and delivery confusion for an online order.

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    #47

    Customer review about a vintage sweatshirt listing showcasing challenges in buying and selling with misleading photos and item condition.

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    #48

    Screenshot of a buyer complaining about a dog food purchase on Vinted, highlighting failed buying and selling experiences.

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    #49

    Buyer wants to cancel purchase due to shipping delay, showing common problems in buying and selling transactions.

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    #50

    Buyer and seller arguing over a dress condition in a frustrating buying and selling interaction online.

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    #51

    Customer confusion over buying and selling reborn baby dolls leading to awkward online exchange.

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    #52

    Chat conversation shows a buyer offended by sale of funeral flowers, highlighting buying and selling things that did not go well.

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    #53

    Chat conversation about stained jeans purchase, refund request denied due to seller's illness, highlighting buying and selling issues.

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    #54

    Online buying and selling conversation showing sizing confusion for a red jumper with a poorly fitting model photo.

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    #55

    Chat screenshot showing a negotiating buyer and seller over a Gymshark T-shirt price, highlighting buying and selling fails.

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    #56

    Buyer comments on seller using excessive tags in Nike running shorts listing, showing buying and selling things did not go well.

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    #57

    Text message exchange showing a buyer frustrated with shipping delays during an online selling transaction.

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    #58

    Chat conversation showing buyer asking for chain thickness comparison, seller sending euros instead of a coin in buying and selling fail.

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    #59

    Chat conversation on buying app where buyer confuses selling clothes with personal chatting in buying and selling fails.

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    #60

    Chat conversation showing buyer confused about paying £1,000 for Adidas top during buying and selling mishap.

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    #61

    Buyer claims missing parcel despite seller’s precautions, illustrating when buying and selling things did not go well with delivery disputes.

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    #62

    Text message exchange showing a heated dispute over buying and selling items involving blocked accounts and accusations.

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    #63

    Chat conversation showing a confusing exchange about buying and selling jewelry with contradictory claims.

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    #64

    Buyer complains about pillowcase quality and microfiber fabric in a buying and selling transaction gone wrong.

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    #65

    Buyer and seller messaging dispute over item shipment and tracking details with negative reviews and cancellation issues.

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    #66

    Chat conversation about buying and selling tech fleece clothing, highlighting doubts and authenticity concerns.

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    #67

    Customer review exchange showing buying and selling conflict with aggressive messages and accusations on a resale platform.

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    #68

    Tweet about selling a leopard print coat on Vinted with buyer's message about a fancy dress in a buying and selling fail.

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    #69

    Chat conversation showing a buyer and seller miscommunication about shipping an ASOS oversized coat, illustrating buying and selling fails.

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    #70

    Chat conversation and listing of a titanium hip for sale, an example of buying and selling things gone wrong.

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    #71

    Improvised shoe wrapped in plastic bags and tape, illustrating awkward buying and selling fails in unusual street setting.

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    #72

    Chat conversation showing a frustrating buying and selling exchange about boots listed for years without selling.

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    #73

    Conversation about worn Ugg boots with a white mark, illustrating buying and selling things that did not go well.

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    #74

    Chat conversation showing a delay in picking up a navy 2-piece suit order in a buying and selling transaction.

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    #75

    Chat conversation about a refund for designer leopard print ski goggles in a buying and selling dispute.

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    #76

    Chat conversation showing buying and selling fail with payment issues during an Xbox series X transaction.

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    #77

    Chat conversation showing a buyer unable to cancel a purchase, illustrating times buying and selling things did not go well.

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    #78

    Chat messages showing a buying and selling mishap with a delayed shipment due to a seller’s hospital admission.

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    #79

    Hand holding a plastic bag with a knitted item inside, illustrating a buying and selling things fail moment outdoors.

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    #80

    Hand holding a poorly packaged black knitted item wrapped in excessive duct tape, illustrating buying and selling fails.

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