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
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#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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#4 She Was Sucking On A Lollipop In One Of Her Photos
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#5 Thought Y’all Would Get A Kick Out Of This
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#6 Dating Apps Are Serious Trash Sometimes
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#7 The Audacity
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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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#10 I Don’t Know, Maybe I Don’t Have Standing To Be Mildly Infuriated About This. Dating Apps Are Wild
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#11 My Friend Just Got A List From Some Guy On Okcupid With 6 Rules/Conditions For Dating Him
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#12 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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#13 Hehehe
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#14 His Bio vs. His Message
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#15 Passive Aggressive After I Wouldn’t Put Out On First Date
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#16 Guys I Got The 4th Ha!!
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#17 Genuinely Bewildered
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#18 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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#19 Why Bother Sending Me A Match Request?
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#20 Guys This Is So Much Fun
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#21 It’s So Over???
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#22 Be Honest, Would This Have Worked On You?
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#23 Dear Jason, You’re Not Funny
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#24 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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#25 Not Even Entertaining It Anymore
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#26 People Who Use AI Photos On Dating Apps
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#27 What Is Wrong With Men?
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#28 Every Asian Girl Who’s Tried Online Dating Will Eventually Get One Of These
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#29 I Hate Dating
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#30 Aaaand That’s Me Finished With Online Dating
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#31 Went On A Date With This Guy Once… Ended After About 45 Minutes
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#32 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
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#33 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
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#34 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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#35 Tried Being Mature And Canceled A Date Whose Location Wasn’t Correct On Their Profile
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#36 I Wouldn’t Even Be Mad At This Reply 😂
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#37 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
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#38 This Guy Wanted Me To Know Just How Disinterested He Is In Me
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#39 I’m So Done With Dating Apps 🤦🏻♀️
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#40 Damn I Got Rejected 😢
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