40 Unhinged Messages From Dating Apps That Are Pure Chaos
Interview With ExpertNavigating 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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I Was Immediately Unmatched. Heartbroken
I wrote this in a reply comment but I have to add it again for my own sanity: Alpha males DON'T EXIST. The concept is taken from studies in 1957 and 1970 of wolf packs in captivity and the term ended up in popular culture as a description for (toxic) masculinity. The theory has been disproven repeatedly (including by Dr L. David Mech, who wrote the 1970 book that popularized the term) but the uneducated keep using it. It drives me crazy when I hear it because it's absolute bullsh*t. Here's a reference (and there are a lot of them): https://www.iflscience.com/the-term-alpha-male-is-all-a-lie-66483
Why Don't You Just Cancel The Date Before I Come There?
She could just as easily done that favor a day earlier.
Load More Replies...In the very least, send someone a simple 'sorry, I changed my mind and don't wanna go a date with you'. Just not showing up and not saying anything, is incredibly mean and rude, I cannot believe that people think this is okay behaviour. When did so many people turn into horrible people who don't give a f**k about other people's feelings?
She really should have texted. Back when I was dating you had to cancel plans or break up in person or on the phone. Now you just text! Easy peasy! Would have saved this guy some time. And just been courteous.
Had that happen a few too many times as well unfortunately. Sometimes before the actual date, “luckily”.
I Love Dating Apps Sooo Much
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.
She Was Sucking On A Lollipop In One Of Her Photos
Thought Y’all Would Get A Kick Out Of This
You must already have 10 years of experience. Sorry, you do not fit the requirements.
Dating Apps Are Serious Trash Sometimes
He waited less than 5 hours. In the middle of the day, when, yes, a lot of people are probably working. Nicely dodged, OP.
Obviously he wasn't working... definitely dodged a bullet here
Load More Replies...SCARY! At least true colors are coming out really fast with these idiots. They don't have the mental capacity to hide their true interior for 5 hours over a message.
I remember there was this guy who was really not my type who kept messaging me on a dating app every time I got back on it. I didn't respond but one time he wrote something about him being ugly and that's why I'm not answering. I tried to be kind and let him know why I haven't (he wasn't my type but wasn't like ugly) then he just kept bugging me and wouldn't take no for an answer. That's why we ignore messages sometimes from incessant men.
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.
The Audacity
Do I Still Have A Chance?
Apparently it's in good tone to celebrate murder, and people are downvoting like crazy anyone who thinks that this is wrong.
Get over yourself. You're either playing ignorant on why people reacted this way. Or you're too blind/stupid to see it. Stop acting like this was some random act of violence and stop trying to ignore the causes. That sh*tstain CEO was PERSONALLY responsible for countless deaths and millions suffering PURELY for his own profit. If you refuse to ignore those fact. It just makes you look like an idiot.
Load More Replies...Not happy he died, just understand the reason. Unfortunately the Orange Felon is making things more deadly for Americans than the healthcare companies have
Load More Replies...Yeah, Why The Hell Are You On A Dating App Anyway?
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.
Most would have stopped that line of questioning after her original answer.
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.
I Don’t Know, Maybe I Don’t Have Standing To Be Mildly Infuriated About This. Dating Apps Are Wild
Always brings to mind to beauty contestant who was asked what her idea of a perfect date was, and responded "March 25th".
I just want to know what the “equality” in the “equality and patience baby” was supposed to say? Lol
Someone told me oine of his hobbie is washing his car. Then he asked when we could meet. I tried to go with the car thing, cos im not judgy (unless there is very good reason), but he felt we had talked enough and wanted to meet. No dude, I have better things to do with my time than wash cars, and I dont have time to waste. So that kinda made me judgy..
I am absolutely not going anywhere with anyone who is not willing to make me comfortable about how well I know them. And all these guys who write “ask me” instead of filling out their dumb profile. No sir. I filled out my stupid profile. We’re doing equal levels of work here. Either you’re willing to put forth effort for a relationship or you’re not. But I’m not putting in more work than you. Stop being lazy and fill out your profile!
Load More Replies...My Friend Just Got A List From Some Guy On Okcupid With 6 Rules/Conditions For Dating Him
I’m sorry, neighbours - my snort-laughing probably woke up half the neighbourhood.
That's okay, I know my guffawing did wake the neighborhood!
Load More Replies...Pity they didn't post the other five rules, I hope they were just as gobsmackingly bad
Imgur.com: https://imgur.com/a/LGC0e. Reddit pulled a BP by scraping just one screenshot, and BP followed suit. At least Reddit included a link in their post.
Load More Replies...The theme song from the original Imagination Ride at Epcot just popped into my head
Load More Replies...A bunch of context is missing. https://imgur.com/a/LGC0e
For those curious like I was. All 6 rules: “Ok, there aren't many rules and I'm sure you'll find most of them quite trivial. Only a few women have balked at them but I think it's because they weren't right for me. Here are the basic rules: 1) You agree not to berate, belittle, besmirch or denigrate my character in any way while we're in public. In private, feel free to say anything you want but I will not have my good name sullied in public. 2) You will not make eye contact with any other men for longer than 2.5 seconds at a time. 2.5 seconds or less can be considered a glance but anything else implies interest in the person you are gawking at. Anything over 2.5 seconds is considered gawking and can be interpreted in you belittling me. This would break rule #1 as well. 3) I would like to be complimented on my physique at least 3 times during our date. Any amount of compliments fewer than that would be considered rude considering that I always try to look my best on a first date. …….
…. Anything less would also be uncivilized. 4) I enjoy fresh air so at least 20% of our date must be held outdoors. If you are averse to outdoor activities we can simply stand outside the restaurant for 20-30 minutes before beginning our date. I'm not too picky about how we arrive at the 20% number. Although you are an attractive lady with sex appeal and I am an attractive man with sex appeal, I would appreciate it if you did not attempt to lure me into your bedroom on the first date. We can negotiate if or when sexual activities will take place on our second date. 6) Kissing or touching is encouraged but not required. If you do not wish to engage in these activities during our first date, you must proclaim that I am desirable in public and at least 3 people must here your words. not kiss our touch me at all then people will take notice and begin to mistakenly believe that I am undesirable. This reduces my status and technically breaks rule #1 as well. You can decide how to state your
Load More Replies...Just Logged Onto A Dating App And This Is One Of The First Messages... Its Not The Creepiest I Know But Still Just Wtf
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.
Hehehe
His Bio vs. His Message
Yeah, without context this entry is a strawman. He is clearly referring to something, and we are being led to assume it is wrong.
True. "Bad boys" can be 2 chickens covered in foil for all we know.
Load More Replies...Passive Aggressive After I Wouldn’t Put Out On First Date
Serious question. Isn't Tinder supposed to be for one night stands?
Nope, it's "supposed" to be for serious relationships
Load More Replies...I said right in my profile that I don't have sex with strangers, so if they thought they would be the exception to just move along. My husband (17 years) said that was one of the things he liked most about me.
“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.
Guys I Got The 4th Ha!!
He was being so sweet and funny. My husband’s idea of romantic phrases usually end up awkward even after +20 years. He admits it Even in the beginning he tried but awwwww hope this guy finds the lady that will appreciate him.
Genuinely Bewildered
I got a 4 wheel drive 5'5" brown eyes and mayby you can handle these...ifykyk.
Think this is closest approximation of what would happen to me. If I tried online dating.
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
I wonder if she was in tears from laughing or crying. I hope she didn't waste emotion on this a*****e and got a good laugh out of it. That's horrible to happen to you the first time you step out of your comfort boundaries
What a tire fire of a person, I feel bad for the OP she seems so nice
Jesus lol “Respect my f*****g details you a*****e dickheaded twatwaffle!!” “Oh ok. I see. Just gonna ghost me like a b***h?!” “I don’t know where I went wrong. We had such a good chat and then she just disappeared. Why do I always pick such a******s! 😭” 🤦🏼♀️🙄
The female version of “nice guy” except you don’t even have to refuse to put out on the first date to offend them 🤷🏼♀️
Load More Replies...Miss Manners needs to write Dear Abby for advice on receiving a personality transplant.
“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.
Why Bother Sending Me A Match Request?
Yes let me take an hour out of the day to iron/fry my hair to please you. Online dating sounds terrifying.
Omg that reminded me of a guy I met on a dating app. We clicked pretty fast and he was cute so we moved to Snapchat even though I dont tend to give my socials fast. I think he asked for a picture so I sent a selfie and he asked me "are you always this ugly" I was f*****g shocked and asked if he was serious. I don't remember what he said but it was a fast block
Guys This Is So Much Fun
I thought this meant "you must be a wizard" because it looks like a muggle trying to enter Diagon Alley
That would represent how a muggle trying to enter platform 9¾ is like the OP trying to enter a relationship with this person
Load More Replies...Plot twist: she was actually looking for her husband to check if he's using the app :))
They're talking to a brick wall because they're only getting one or two word answers back.
Load More Replies...It’s So Over???
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
I’ve been out with men that have very little going for them who think they can coast on their height. It’s weird. I’d rather have a shorter guy who actually has something going for him.
In their defense, they probably can coast on their height given the number of women that fetishize it.
Load More Replies...She's looking for a guy that can carry her around in his pocket
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.
Be Honest, Would This Have Worked On You?
This was hilarious and I'd respond in kind. Not everyone has that kind of humor, i think.
Interlock toes? I'd ask how that even works but I'm afraid someone would try to explain it to me.
Yes! My aunt and I had toes that could do that. People I told thought I was crazy. Yeah but that’s besides the point.
Load More Replies...Unless your feet are smooth with a perfect manicure, no footsies. Rough nails hurt...
Dear Jason, You’re Not Funny
Coming from a black person they always think its a joke worthy of a killer head, but its not and never will be.
Load More Replies...Talk about decorum and common sense flying out of the window. Why, oh why?
This Person (28f) Frequently Complains On Social Media About How Badly Guys Treat Her. I (35m) Am Genuinely Starting To Hate Dating
That full stop after ‘lying’ really threw me. Then it got worse.
"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.
Not Even Entertaining It Anymore
Maybe she needed help putting the groceries on the highest shelf
That's it! She needs help putting up her groceries!!
Load More Replies...I know! 👍 You are too lazy to get a stool for those top shelves in the kitchen, and trying to poke things down with a long spoon or the kitchen broom is 50/50 if you succeed or get the thing at your head/on the floor. 😉
Load More Replies...People Who Use AI Photos On Dating Apps
Its too busy digging its own grave with all the bs ads and premium nonsense to jump sharks.
Load More Replies...This AI dude's got five fingers and a thumb, on one hand Very prosperous!
Yes but a total of 10 fingers, which is astonishing for an AI pic.
Load More Replies...What is it with the ‘here’s me in front my car looking smug’ pictures? They’re cringe enough even without AI.
For me, the funny part is i dont recognise most cars so i would not be impressed.
Load More Replies...What Is Wrong With Men?
“No, but I’ve always wanted to try it. My place or yours? I’ll bring the biggest strap on I can find! 😁”
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?
Every Asian Girl Who's Tried Online Dating Will Eventually Get One Of These
‘I am wealthy and have a lot of status’ = ‘I have the personality of a gangrenous s*****m wart and the looks to match’
Do you mind if I still gangrenous s*****m wart?? I really like that.
Load More Replies...I have an Asian wife and so I know many others with Asian wives. I can assure him that they are not docile and submissive.
As an Asian woman, I have no idea where that stereotype came from. In Korea, people tend to like women for having strong worth ethics and being stubborn. We like good workers! 💪💪
Load More Replies...Ew ew ew I feel like worms are crawling through my body reading that I am so uncomfortable right now
"I manage million dollar accounts...". Dude must be really old if he thinks a million is impressive.
I Hate Dating
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.
It is the digital equivalent of sweaty construction workers howling, barking and making loud smoochy noises at attractive ladies walking by. Doubt they had a high success rate either.
Load More Replies...Why does any guy think a woman is going to be turned on by the phrase "destroy your insides"? Would these men get turned on if a woman would say "I wanna ride you until your d*** is bloody and bruised"?
Aaaand That’s Me Finished With Online Dating
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.
No "future", and not a sociopath. The man is presently a full-on psychopath.
Load More Replies...Went On A Date With This Guy Once... Ended After About 45 Minutes
I wanna put a [dutch] baby in you. That would work way better.
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
Reply to nottheactualphoto: there's enough charge to phone 911, 999 or whatever their emergency number is.
The caption says she already contacted the police but maybe it didn’t when you saw it (judging from other comments)
Load More Replies...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
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 😭
At least he was honest from the jump and didn't have to find out after perhaps getting to like him. Its a fast track no go and that's amazing.
Repeat after me “just because it isn’t illegal, does not mean it is morally right or okay!”
Tried Being Mature And Canceled A Date Whose Location Wasn’t Correct On Their Profile
I do not like long distance, and I think that I have lived within less than 30 minutes of the guys who I have dated.
I Wouldn’t Even Be Mad At This Reply 😂
I hope this hateful dipshit goes skydiving without his parachute next time.
So nice when they show who they really are with just a sentence or two.
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
Surely that last line gets you every time, doesn't it, ladies?
Probably able to look up your email address or Snapchat username and mess able to find you from there or just got a friend suggestion because of the username search. Not always sinister, especially these days with AI s**t. It’s like thinking about something then suddenly it’s being suggested everywhere, although, I DO understand the concern.
I don't understand the photo context of Squidward and what is blocked out under "cyberbully"?
Cum. Under cyber bully and squidward is always grumpy and angry so I would guess that’s what he’s there for since it says “down bad today aren’t we?” But I couldn’t tell you lol
Load More Replies...Why did she continue on with the conversation? And that pic she sent; slightly inappropriate
Well yes, it would be if it didn’t say cyberbully instead of cum lol
Load More Replies...This Guy Wanted Me To Know Just How Disinterested He Is In Me
He kept count? But he’s not interested? And she has no idea who he is and she’s the one that’s “relentless”? lol isn’t Opposite Day?
They don't even remember. I have good memory and been some time on dating apps. They put the same photos and change accounts surprisingly often. But can't actually remember whomever they liked so I had many incels repeatedly like/text/whatever me and being the same surprised after next and next rejection.... And if you use different photo they are absolutely lost 😂
I’m So Done With Dating Apps 🤦🏻♀️
In guy speak, he was willing to check your oil levels, but wasn't interested in a relationship with her for whatever reason whether it be something in her bio that he knew wouldn't mesh, like maybe she's very religious or something. Either something along those lines, or he just wasn't that attracted to her appearance.
Damn I Got Rejected 😢
Been Back On Dating Apps One Day
He Unmatched Me
She Ghosted Me And Sent Me This 10 Days Later
What Should I Respond?
Low Effort Date Rejection
Umm… I’m Confused
One Date And A Month Of No Talking Sand I Suddenly Get This
They think they'll eventually find THE ONE who'll entertain their bs.
Load More Replies...Went On A First Date With A Guy Last Night- Thoughts?
why are you telling a guy you just went on a first date with about a guy following you home from the gym?
I'd probably have asked why is this guy offering to shoot someone to a woman he just went on a first date with? (Or to anyone really)
Load More Replies...People all over the US have guns and are idiots with them.
Load More Replies...This Man Is 29. I Am 31. I Am Done 🪦
Short Kings
Not exactly short but different from the normal pattern
My First Date Admitted I Was Talking To AI The Whole Time On Bumble
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.
I’m betting he used it write the apology text too…
Load More Replies...To be fair ai xan be quite clever
Load More Replies...1st Attempt At Online Dating And My Colleague Gets This. 🤮
This Vexes Me
Literally just started a rewatch of the whole show after a long time, forgot how much I enjoyed it!
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
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’.
One thing to remember though, some people have an open relationship but don't tell that to their friends because of the taboo, and assume that there's only a super small chance that someone you know is gonna match with you on a dating app and find out. (Because if someone only sees your profile, you can just say it's an old undeleted one)
... Or Maybe That Was Just A S**t Thing For You To Say??
This Can’t Be For Real
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??
Whoaaaaa
He Was Quite Into Marriage And Children On The First Date And While I'm Sure He Was Making A Joke....yikes
No Wonder We're Both Single
Worst Part Is I Posted Selfies In R/ Teenagers
Randomly Blocked By This Girl I Had A Date With Tonight
The blue ones are iMessages and they use the internet. The green one is a text message, the recipient probably didn’t have signal or they blocked them. 🤷♀️
Load More Replies...If you can’t handle me at my fried Oreos, you don’t deserve me at my Cream of Wheat
Is Not Having Social Media A Red Flag?
I mean apparently you're a lot less likely to be hired without any form of social medias, so according to companies- yep
That’s Rough Buddy
How Am I Even Supposed To Come Back From This
It Worked
Though this post is cute / It's on the wrong list / I think they're a match / You get the gist
I hope it worked out/ill check and update in time/i dont know what to say here/its difficult to rhyme
Load More Replies...What Happened To “Hello?” “How Are You?”
Im 18 And He’s 25. Did He Not See My Age When He Swiped On Me?
Was That Not A Valid Answer To Her Opening Move?
Dating Apps In A Nutshell
Thanks Bumble!
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?
Yup. I have got the gist of this online dating app thing. If my husband ever dies, i will never date again.
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.
I lost my husband a few years ago. I'm never going on any dating app, hell, I'll probably never date again. I was lucky enough to marry a truly decent man. No one could ever come close to him so I'll save myself the trouble of looking for something I'll never find again.
I like reading these. Helps me get my daily dose of cringe so I don't have to go back in my personal archives lol.
Kinks should probably not be one of the first things talked about guys
Best thing is to go to specific sites for kinks. Unlikely to find what you want on a vanilla dating site.
Load More Replies...Yup. I have got the gist of this online dating app thing. If my husband ever dies, i will never date again.
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.
I lost my husband a few years ago. I'm never going on any dating app, hell, I'll probably never date again. I was lucky enough to marry a truly decent man. No one could ever come close to him so I'll save myself the trouble of looking for something I'll never find again.
I like reading these. Helps me get my daily dose of cringe so I don't have to go back in my personal archives lol.
Kinks should probably not be one of the first things talked about guys
Best thing is to go to specific sites for kinks. Unlikely to find what you want on a vanilla dating site.
Load More Replies...
