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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

Chaotic dating app conversation featuring a self-proclaimed alpha male and a skeptical response.

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Nathaniel He/Him Cis-Het
Community Member
1 day ago (edited) DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

As an Alpha male, I just have to tell all you men out there, if you have to state you are an Alpha male, you are not an Alpha male. Trust me, I am an Alpha male.

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    #2

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

    Unhinged dating app message recounts a canceled date with accompanying image of yellow flowers.

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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.

    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.

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    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

    Dating app messages showing chaotic conversation with one apologizing for not responding.

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    StarCrossedFriday
    Community Member
    1 day ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

    He waited less than 5 hours. In the middle of the day, when, yes, a lot of people are probably working. Nicely dodged, OP.

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    #9

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

    Chaotic dating app message conversation about agenda and attraction.

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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.

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    #10

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

    Chaotic exchange on a dating app with cheeky and blunt responses, highlighting unhinged messages in dating scenarios.

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    #12

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

    Dating app message with chaotic rules about kissing, touching, and public proclamations of desirability.

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    StarCrossedFriday
    Community Member
    1 day ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

    I’m sorry, neighbours - my snort-laughing probably woke up half the neighbourhood.

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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

    Unhinged dating app message with chaotic toilet emoji request and a response pointing to a subreddit.

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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

    Chaotic dating app messages exchange discussing profile information misunderstandings.

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    #17

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

    Online dating profile message showcasing unhinged and chaotic behavior with a focus on personal wealth and preferences.

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    #18

    Guys This Is So Much Fun

    Chaotic dating app conversation ending with a humorous image of a boy facing a brick wall.

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    Nice Beast Ludo
    Community Member
    12 hours ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

    I thought this meant "you must be a wizard" because it looks like a muggle trying to enter Diagon Alley

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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.

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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

    Be Honest, Would This Have Worked On You?

    Chaotic dating app exchange about sleeping with socks and interlocking toes, highlighting unconventional romance.

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    #23

    Aaaand That’s Me Finished With Online Dating

    Chat showcasing unhinged dating app messages with a dark and chaotic conversation about animals.

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    StarCrossedFriday
    Community Member
    1 day ago (edited) DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

    It’s weird that their eyes turn lifeless after they get shot in the head? But he doesn’t think this style of introduction is weird?

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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.

    #26

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

    A chaotic dating app message discussing relationship expectations and financial support.

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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.

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    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?

    #29

    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 😭

    Chaotic dating app message discussing relationship age differences in a concerning conversation.

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    #30

    Went On A Date With This Guy Once... Ended After About 45 Minutes

    Chaotic dating app message displayed against a dark background.

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    #31

    Guy Saw Me On A Dating App (Where I Did Not List My School), Looked Me Up In A School Registry & Messaged Me Via Microsoft Teams

    Message screenshot from a dating app showing chaotic humor with "FYI I saw your profile and swiped right lol".

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    #32

    I Hate Dating

    Chaotic message exchange on a dating app showcasing unhinged communication styles.

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    StarCrossedFriday
    Community Member
    1 day ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

    The more I read these, the more it becomes apparent people come up stuff like this and expect some kind of good outcome, it’s deeply worrying.

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    #34

    I Went On A Date With This Guy A Couple Days Ago, I Have Never Been So Creeped Out By Someone. The Picture He Sent Me Is Of My Apartment Building. I Already Contacted The Police

    Chaotic dating app messages with frantic texts followed by an image of a blurred car view.

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

    Reply to nottheactualphoto: there's enough charge to phone 911, 999 or whatever their emergency number is.

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    #35

    This Guy Wanted Me To Know Just How Disinterested He Is In Me

    Chaotic dating app conversation; one user accuses another of repeatedly liking their profiles over years, leading to an awkward exit.

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    #36

    For Context: Met This Guy Through A Dating App About Three Months Ago. Never Actually Met But Spoke Through Snapchat. I’ve Had A Boyfriend For Two Months Now And I Have No Idea How This Guy Found Me On Facebook Considering I Never Told Him My Last Name

    Unhinged messages from a dating app conversation filled with awkward exchanges and memes.

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    #38

    Tried Being Mature And Canceled A Date Whose Location Wasn’t Correct On Their Profile

    Chaotic dating app messages discussing meeting halfway and long-distance relationship experiences.

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    #40

    I Wouldn’t Even Be Mad At This Reply 😂

    Unhinged dating app conversation about parachuting and skydiving, ending with an apology.

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    Note: this post originally had 71 images. It’s been shortened to the top 40 images based on user votes.