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40 Unhinged Messages From Dating Apps That Are Pure Chaos

Navigating dating apps can feel like stepping into the wild—you never know what kind of messages are waiting for you. While some people find sweet connections, others are left wondering how basic human interaction went so wrong. From hilariously bad pickup lines to messages that make you question reality, modern dating is nothing short of unpredictable. And then there are those moments so awkward, so cringe-worthy, that they simply have to be shared. The internet is full of people documenting their weirdest dating app encounters, and we’ve gathered some of the most jaw-dropping examples. Keep scrolling to see the funniest, most bizarre, and most painfully awkward messages people have received!

#1 I Was Immediately Unmatched. Heartbroken

Image credits: Legen_unfiltered

#2 Why Don't You Just Cancel The Date Before I Come There?

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#3 I Love Dating Apps Sooo Much

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Finding love isn’t exactly a walk in the park. Whether you go the old-school route with a blind date set up by your sister’s coworker or dive into the world of dating apps, the struggle remains the same.

The search for a meaningful connection can sometimes feel like an endless maze of awkward encounters, mismatched expectations, and, let’s be real—some truly bizarre interactions.

#4 Thought Y’all Would Get A Kick Out Of This 🙄😭😂

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#5 She Was Sucking On A Lollipop In One Of Her Photos

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#6 The Audacity

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These days, online dating is more popular than ever. According to the Pew Research Center, nearly three in ten U.S. adults have used a dating site or app. But it’s not all sunshine and romance.

In fact, recent findings reveal that 45% of users feel frustrated by the experience, while only 28% remain hopeful. It turns out that swiping left and right isn’t as simple as it seems—it comes with its own set of emotional highs and lows.

#7 Dating Apps Are Serious Trash Sometimes

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#8 Do I Still Have A Chance?

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#9 Yeah, Why The Hell Are You On A Dating App Anyway?

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It can be exhausting to keep scrolling through profiles, hoping to find someone who actually clicks. Hours of chatting might lead to ghosting, awkward first dates, or even the realization that someone’s profile picture was taken ten years ago. The entire process can leave people questioning if love was easier to find before technology took over.

#10 Passive Aggressive After I Wouldn’t Put Out On First Date

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#11 I Don’t Know, Maybe I Don’t Have Standing To Be Mildly Infuriated About This. Dating Apps Are Wild

Image credits: Jen_With_Just_One_N

#12 His Bio vs. His Message

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To understand the complexities of modern dating, we spoke with relationship coach Jay Bhaskar from Gujarat, India. He believes that impatience plays a major role in the struggles of online dating.

"People want instant results. They don’t want to invest time in getting to know someone," he explains. This rush to find "the one" often leads to impulsive decisions and miscommunication.

#13 Just Logged Onto A Dating App And This Is One Of The First Messages... Its Not The Creepiest I Know But Still Just Wtf

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#14 Genuinely Bewildered

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#15 My Friend Just Got A List From Some Guy On Okcupid With 6 Rules/Conditions For Dating Him

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“In an attempt to stand out, people sometimes end up saying things that come off as odd or even inappropriate,” Bhaskar adds. While confidence is key, there’s a fine line between being charming and being cringeworthy. And as dating app users know too well, not everyone gets that memo.

#16 Decided To Try Out A Dating Site For The First Time Where You Have To Text People. Creeped Me The Heck Out How She Went From 0-100 So Quick

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#17 Every Asian Girl Who's Tried Online Dating Will Eventually Get One Of These

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#18 Not Even Entertaining It Anymore

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“Sometimes, what people mean and what they actually say are two completely different things," he continues. "A joke meant to be funny might land the wrong way, or an innocent compliment might sound forced or awkward." The lack of real-time social cues in text-based conversations makes things even trickier.

#19 Guys This Is So Much Fun

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#20 Be Honest, Would This Have Worked On You?

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#21 This Person (28f) Frequently Complains On Social Media About How Badly Guys Treat Her. I (35m) Am Genuinely Starting To Hate Dating

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One of the biggest downsides of online dating, Bhaskar points out, is the lack of filters. “People don’t hold back. There’s a certain level of anonymity that makes them feel they can say whatever they want, without facing the consequences.” This can result in interactions that range from rude and inappropriate to downright shocking.

#22 Aaaand That’s Me Finished With Online Dating

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#23 Why Bother Sending Me A Match Request?

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#24 Guys I Got The 4th Ha!!

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"There’s no real accountability," he says. "If things go wrong, people can just unmatch or block the person and move on without any explanation." While this can be useful in some cases, it also leads to a dating culture where ghosting and abrupt endings have become the norm.

#25 People Who Use AI Photos On Dating Apps

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#26 It’s So Over???

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#27 Met This Divorced Man On Tinder. Dude Is 40 And Has 3 Kids With This Woman. I Think I’m Going To Stop Dating For A While 😭

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Writer Magdalene J. Taylor summed it up perfectly in an opinion piece for The New York Times: “Dating apps treat people like commodities and encourage us to treat others the same. We are not online shopping. We are looking for people we may potentially spend our lives with.” The endless swiping and quick judgments often take away the human element from dating, making genuine connections harder to form.

At the end of the day, dating—whether online or offline—isn’t just about finding the right person; it’s also about presenting yourself in the best way possible. And as these posts prove, some people definitely missed that memo. If nothing else, these dating app fails serve as a hilarious reminder of what not to say to your date! Which one made you cringe the most?