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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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Rosecrucian Roeth
Community Member
16 hours ago Created by potrace 1.15, written by Peter Selinger 2001-2017

Why would you order if the reviews seem to have a recurring theme of her lying?

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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

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

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    Upstaged75
    Community Member
    23 hours ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    Well that's just sad. How do you get khaki from car key??

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    #3

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

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    Mobey Drunk
    Community Member
    Premium
    18 hours ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    I think this was an ad for a cyber truck.

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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.”

    #5

    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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    Laughing Orc
    Community Member
    23 hours ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    Much rather have the baked beans than any association with the UK's home-grown MAGA wannabes.

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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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    Laughing Orc
    Community Member
    23 hours ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    Why are the words "police" and "theft" in need of censoring....?

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    #7

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

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    Chad Olin
    Community Member
    6 hours ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    I had someone do this to me literally THREE months after I bought it for a birthday gift. They insisted I get it back and return it because it was sold by mistake and it was a sentimental item to them. I had already given it away and they were adamant about getting it back. My guess it could be the same person above who wants the shirt back, lol. Some people just don't get how the internet works...or life, either.

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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

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

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    Mike F
    Community Member
    21 hours ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    Wow, they have those on the other side of the pond as well?

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    #10

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

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    Upstaged75
    Community Member
    23 hours ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    This sounds like a conversation with CrystalWitch. 😂

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    #11

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

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    Owen
    Community Member
    Premium
    1 hour ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    Nailed it.

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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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    Michael Largey
    Community Member
    23 hours ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    Apparently her knitting wasn't the only thing she was tending to.

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    #14

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

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    poiplescales
    Community Member
    18 hours ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    Most library computers require your library id to log in to print things

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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.

    #16

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

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    Ace
    Community Member
    Premium
    12 hours ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    That's one odd-looking dog bite.

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    #17

    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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    Laughing Orc
    Community Member
    23 hours ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    Totally reasonable, theres just no possible way to take that extremely robust can apart to free his very definitely stuck finger without going to A&E.

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

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    Upstaged75
    Community Member
    23 hours ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    Condition is the word I believe they're looking for.

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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.

    #22

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

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    Debby Keir
    Community Member
    7 hours ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    So she's selling on a website, and he can't find any other way of contacting her (cos he's blocked) so uses her selling page to communicate. Clunky but enterprising.

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

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    Owen
    Community Member
    Premium
    1 hour ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    Maybe I'm pointing out the obvious here but she managed to take a picture of herself from outside of where she was trapped. All this effort for a £1 T shirt.

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    #25

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

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    Upstaged75
    Community Member
    23 hours ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    Magaluf is a resort town in Spain. I had to look it up to understand this one.

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    #26

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

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    Crystalwitch60
    Community Member
    10 hours ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    🤣🤣🤣🤣🤣really omg that’s just pathetic!,

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    #27

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

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    V
    Community Member
    18 hours ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    Can you block and report? Because that's what I would be doing

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    #28

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

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    wbb57sdjqc
    Community Member
    Premium
    7 hours ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    tbf this does seem like quite a rude reaction when it wasn’t being messed around that much tbf. like i had to put a pic up of a dress to reserve it seperate and got no response and was unbothered. didn’t lose much from it cept five mins on my phone 🤷‍♀️ seems like they was gonna buy - no proof of lie

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    #29

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

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    Owen
    Community Member
    Premium
    1 hour ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    I smell a long story of bullsh*t. Just give the clown away you absolute donut.

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    #30

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

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    Mike F
    Community Member
    21 hours ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    This is a verbal tennis match. Click the link, holy cow.

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    #31

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

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    Owen
    Community Member
    Premium
    1 hour ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    I wear a leather jacket. They do not cost £20,000. Maybe I got a bargain?

    #32

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

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    Owen
    Community Member
    Premium
    1 hour ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    He knows what he's about.

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    #33

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

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    Owen
    Community Member
    Premium
    1 hour ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    Their one is special because of the added sentimental value.

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    #37

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

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    Debby Keir
    Community Member
    7 hours ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    I'm glad they explained what that mark was!

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    #41

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

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    Upstaged75
    Community Member
    22 hours ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    I would pay just to have them throw that cake away. 😂 It's cursed.

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    #42

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

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    Mike F
    Community Member
    21 hours ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    And now the child is crying, right?

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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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    BioMom
    Community Member
    1 hour ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    I need someone to translate...

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    #48

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

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    Ronja Oksanen
    Community Member
    8 hours ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    Can't even sell old shiiit without these slimebags 😵‍💫

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    #49

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

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    Jp@nda
    Community Member
    1 hour ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    That's sad, just cancel the freaking order

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    #50

    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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    Cee Cee
    Community Member
    15 hours ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    Evri has to the one of the worst delivery firms in the UK. Last weekend found one ferreting around in my basement light well. Told me he could read the note on my front door from his van saying I was in. Took a lid from my recycling bin. Refused to give me the parcel. Came back with it 20 mins later. Then put his foot in my door. Needless to say no response from Evri customer service or the CEO. Unfortunately Evri is the default option for many EBay sellers.

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    Note: this post originally had 80 images. It’s been shortened to the top 50 images based on user votes.