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40 Unhinged Messages From Dating Apps That Are Pure Chaos
Interview With Expert
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!
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#1
I Was Immediately Unmatched. Heartbroken
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#2
Why Don't You Just Cancel The Date Before I Come There?
#3
I Love Dating Apps Sooo Much
#4
She Was Sucking On A Lollipop In One Of Her Photos
#5
Thought Y’all Would Get A Kick Out Of This
#6
Dating Apps Are Serious Trash Sometimes
StarCrossedFriday 1 year ago
He waited less than 5 hours. In the middle of the day, when, yes, a lot of people are probably working. Nicely dodged, OP.
#7
The Audacity
#8
Do I Still Have A Chance?
#9
Yeah, Why The Hell Are You On A Dating App Anyway?
Celtic Pirate Queen 1 year ago
I luckily only went on 5 internet dates until I met my husband (17 years ago). I met one guy at my local. I was early so I ordered a glass of wine. He showed up 15 minutes late, acting like he didn't even want to be there & no apology. Okay, whatever. We start the usual chit chat and I ask what he does (job). He asks, "why? So you can figure out how much money I make? Maybe I should just show you my bank statement." I literally stood up and said, "WOW. F*ck you. No amount of money would make up for your personality" and walked out. I just went around the block and watched him leave. The bartender handed me my wine from behind the bar and was blown away at what a jerk he was.
#10
I Don’t Know, Maybe I Don’t Have Standing To Be Mildly Infuriated About This. Dating Apps Are Wild
#11
My Friend Just Got A List From Some Guy On Okcupid With 6 Rules/Conditions For Dating Him
StarCrossedFriday 1 year ago
I’m sorry, neighbours - my snort-laughing probably woke up half the neighbourhood.
#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
#14
His Bio vs. His Message
#15
Passive Aggressive After I Wouldn’t Put Out On First Date
#16
Guys I Got The 4th Ha!!
#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
#19
Why Bother Sending Me A Match Request?
#20
Guys This Is So Much Fun
Nice Beast Ludo 1 year ago
I thought this meant "you must be a wizard" because it looks like a muggle trying to enter Diagon Alley
#21
It’s So Over???
Nice Beast Ludo 1 year ago
My husband is 5'3 like me. We walk instep and everything. My ex was 6'7. I barely came up to his chest. I like being the same height much more than having someone tower over me
#22
Be Honest, Would This Have Worked On You?
Jess Bertram 1 year ago
This was hilarious and I'd respond in kind. Not everyone has that kind of humor, i think.
#23
Dear Jason, You’re Not Funny
#24
This Person (28f) Frequently Complains On Social Media About How Badly Guys Treat Her. I (35m) Am Genuinely Starting To Hate Dating
#25
Not Even Entertaining It Anymore
#26
People Who Use AI Photos On Dating Apps
#27
What Is Wrong With Men?
#28
Every Asian Girl Who's Tried Online Dating Will Eventually Get One Of These
StarCrossedFriday 1 year ago
‘I am wealthy and have a lot of status’ = ‘I have the personality of a gangrenous s*****m wart and the looks to match’
#29
I Hate Dating
StarCrossedFriday 1 year ago
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.
#30
Aaaand That’s Me Finished With Online Dating
StarCrossedFriday 1 year ago (edited)
It’s weird that their eyes turn lifeless after they get shot in the head? But they doesn’t think this style of introduction is weird? Edit: thanks, Karina, good point - we don’t know if it’s a man or a woman.
#31
Went On A Date With This Guy Once... Ended After About 45 Minutes
#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
#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
#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 😭
#35
Tried Being Mature And Canceled A Date Whose Location Wasn’t Correct On Their Profile
#36
I Wouldn’t Even Be Mad At This Reply 😂
#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
#38
This Guy Wanted Me To Know Just How Disinterested He Is In Me
#39
I’m So Done With Dating Apps 🤦🏻♀️
#40
Damn I Got Rejected 😢
#43
She Ghosted Me And Sent Me This 10 Days Later
#47
One Date And A Month Of No Talking Sand I Suddenly Get This
#48
Went On A First Date With A Guy Last Night- Thoughts?
#49
This Man Is 29. I Am 31. I Am Done 🪦
#50
Short Kings
#51
My First Date Admitted I Was Talking To AI The Whole Time On Bumble
QueenKittyCat 1 year ago
AI is entering our lives too much. At the very least the guy could have read everything in addition to being honest before the date.
#52
1st Attempt At Online Dating And My Colleague Gets This. 🤮
#53
This Vexes Me
#54
Found My Friend's Husband On Tinder. I Don't Know What To Do :( Does Tinder Recycle Old Accounts, Did He Just Forget To Delete His? I Don't Want To Ruin Their 8-Year Marriage
StarCrossedFriday 1 year ago
Honestly, just to start with satisfying my own curiosity, I’d probably make a fake profile. If he replies and goes for it, I’d bring his wife along for our ‘date’.
#55
... Or Maybe That Was Just A S**t Thing For You To Say??
#56
This Can’t Be For Real
#57
I (24f) Am Open To Dating Older Guys So I Matched With This Guy (48m) And He Sent Me This… At Least He’s Honest??
#58
Whoaaaaa
#59
He Was Quite Into Marriage And Children On The First Date And While I'm Sure He Was Making A Joke....yikes
#60
No Wonder We're Both Single
#61
Worst Part Is I Posted Selfies In R/ Teenagers
#62
Randomly Blocked By This Girl I Had A Date With Tonight
#63
Is Not Having Social Media A Red Flag?
#64
That’s Rough Buddy
#65
How Am I Even Supposed To Come Back From This
#66
It Worked
#67
What Happened To “Hello?” “How Are You?”
#68
Im 18 And He’s 25. Did He Not See My Age When He Swiped On Me?
#69
Was That Not A Valid Answer To Her Opening Move?
#71
Thanks Bumble!
Potato patato 1 year ago
I went to the reddit post to find the missing context and the second image is of them happily married, so that's happy at least?
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What do you think ?
Jess Bertram 1 year ago (edited)
Yup. I have got the gist of this online dating app thing. If my husband ever dies, i will never date again.
Pencil 1 year ago
Many, many years ago I was on Match. My profile said looking for a serious relationship only. Got a message from a guy and we emailed a bit. He asked about my background or something, don't remember exactly but it was normal and fine. I mentioned that I'm half Jewish. He replied that he was a white supremacist so obviously couldn't date me but not to worry, he'd still do me doggy-style. So that was one to remember.
Jess Bertram 1 year ago (edited)
Yup. I have got the gist of this online dating app thing. If my husband ever dies, i will never date again.
Pencil 1 year ago
Many, many years ago I was on Match. My profile said looking for a serious relationship only. Got a message from a guy and we emailed a bit. He asked about my background or something, don't remember exactly but it was normal and fine. I mentioned that I'm half Jewish. He replied that he was a white supremacist so obviously couldn't date me but not to worry, he'd still do me doggy-style. So that was one to remember.
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