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My Dating Nightmare: Guy 'Owned Plane', But Shared A Bedroom With Two Brothers

Bad dates make great stories, especially when the date completely crashes and burns. Like this one!  We teamed up with The Single Society to share all of the dumpster fire dating disasters women face in this bizarre era that is digital dating. If you have a trainwreck dating story like this one, share that sh*t here! 

dating fail about guy who owned a plane but shared bedroom with two brothers | thumbnail pop art image of guy in plane Text - How about you buy me some drinks and I will tell you all about my plane? | would rather share 600 square feet brothers than give up my plane proclaimed as made me pay $100 worth of tequila downed on our date
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Dating Nightmares: Craziest Things People Found After Googling Their Date

The internet is a great way to meet a potential partner! It is always a great way to dig up some dirt that they may be hiding! We teamed up with The Single Society to bring you all the crazy stories in the online dating world. Here are 9 cases where someone found out that their date was a less than desirable candidate by using the good 'ol Google! Have a crazy online dating horror story? Share it with us

bad dating stories about crazy things women found when googling their dates | thumbnail includes pop art graphic of woman at computer Text - I'm dating a sex offender?! | Turns out, the guy had THREE cases of sexual assault and battery he had been convicted of within the last five years (he was 34). When I confronted him about it via text he told me he had a crazy ex-girlfriend. Likely story.
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Dating Nightmares: Rude Things Men Have Done On First Dates

Some people are just plain rude. Especially the plethora of assholes on the dating apps these days! We teamed up with The Single Society to share the fabulously bad stories of online dating disasters and the crazy things people ACTUALLY have the balls to say and do. It's not pretty, but it's pretty fucking hilarious.

bad dating stories about guys who were rude on first dates | thumbnail pop art graphic of man and woman Text - not to be rude, but what is your cup size | A guy I was on a date with kept texting and looking at his phone. Finally, I asked him what was going on. Turns out he was arguing with his ex about taking me to a place they used to go
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My Dating Nightmare: Explosive Diarrhea Disaster On Halloween

Online dating can be a terrifying feat. But one of the MOST terrifying things on earth can be your gastrointestinal system….especially since it can strike when you least expect it! Put those two things together and add in a haunted house with no bathroom and sh*t can be straight-up horrifying…Literally! Together with The Single Society, we're sharing these dating disasters with the world, and here is one of the spookiest, by far!

dating fail about a guy who had diarrhea on first date on halloween | thumbnail Text - I just shit my pants | Apparently, the scariest thing about this evening was Bryce's gastrointestinal system because he sh*t his pants right in the middle of the haunted house.
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My Dating Nightmare: The 'Recovering' Alcoholic Who Stabbed Ex-Wife With Fork

There are some crazy people in the world, and many of them can be found on dating apps! But no GOOD story ever started with 'I met a nice normal guy….' Like this weirdo who clearly has a little emotional baggage (and maybe some anger issues) to deal with. We teamed up with The Single Society to share all the crazy dating experiences from women all over the world! You're welcome. 

dating fail story about guy who stabbed ex-wife with fork | thumbnail pop art image of guy Text - "give me a chance or I'll throw my fork at you" | He how his drugs and alcohol addiction caused him to lose his job and ruin his first AND second marriage by drunkenly trying to stab his ex-wife with a fork in a restaurant, resulting in incarceration.
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Dating Nightmares: Women Who Had to Deal With Total Stalkers After A Date

I think I speak for every single person when I say the modern dating scene can be pretty scary. But for someone unlucky ladies it can be downright terrifying. People not taking hints or even accepting a blatant rejection rearing their ugly heads can be undoubtedly frightening. We teamed up with The Single Society to tell you all about these spooky encounters from people who just couldn't take 'no' for an answer.

Women who had to deal with a total stalker after a date | thumbnail pop art image of man on computer Text - She blocked me again?! Time to find out where she works | l met a guy online and went on one mediocre date. I didn't respond to any of his texts, hoping he would get the hint. He didn't, and started calling the front desk at my work multiple times a day and leaving messages on my machine. The secretary had to block his number
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Dating Nightmares: Horrific Halloween Walk of Shame Stories

A good walk of shame (or stride of pride) story is always good for a laugh...especially after Halloween! Who doesn't love the thought of a sexy nurse or a giant banana trekking across town after some good old-fashioned adult fun! We teamed up with The Single Society to share some of the most horrific and hilarious 'walk of shame' stories. Enjoy! And maaaaaybe think about bringing a change of clothes for future Halloween parties. Just a thought!

dating stories about halloween walks of shame | AHH... THE SWEET REGRET OF A HALLOWEEN WALK OF SHAME | crashed at sorority house and since pretty hot that weekend only wore pair of underwear under my costume. didn't think would be issue because would be going home. had to walk back my house still dressed giant penis
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My Dating Nightmare: Bad Tipper Who Proved Chivalry Is Dead

What happens when you go on an awful date with an unchivalrous asshole AND a bad tipper? Well, we write it down and post it on the Internet for all to read and enjoy, of course! This is of course, why we teamed up with The Single Society, so we can share all of the dating disasters that happen to unlucky singles every day. Remember to tip your bartenders!  

dating fail story about guy who only gave the tip | thumbnail pop art image of woman "I like getting more than just the tip, but this wasn't what I had in mind" | Craig pulled out disheveled one dollar bill few dimes nickels from his pocket. He then put dollar back into pocket leaving only change behind. just don't think we should be responsible for paying salary
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People Reveal The Freakiest Requests They Had During Sex

Who doesn't love a good 'ol fashioned toss in the sack? Sex can be a beautiful (and fun) way to pass the time. Whether someone has a dirty little fetish or an unfulfilled sexual fantasy people can certainly get...creative when it comes to their preferences in the bedroom. We have teamed up with The Single Society to bring you all these freaky things people were asked for during sex. Yikes!

Freakiest things people have asked for during sex | thumbnail pop art picture man and woman lying in bed text - I met a guy on one of the dating apps and we went home together. He had some strange baby fetish. He asked me to remove his underwear and wipe him with baby wipes before we started having sex. It got weird. I left.
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My Dating Nightmare: Financially Irresponsible Golfer Who Wasn't Up To Par

In this digital dating era, there is never a dull moment when it comes to the search for a potential mate. As they say, you have to kiss a few frogs to find a prince! We teamed up with The Single Society to bring you all the details of the cringe-worthy experiences while kissing these fabulously horrible - and hilarious- frogs. Read about this awful golfing date that was definitely a swing and a miss. Have an awful date story to share? Speak up and share it here! We'd love to hear it. 

Dating fail story about Financially Irresponsible Golfer Who Wasn't Up To Par | thumbnail pop art woman holding golf club Text - "my love life is one giant swing and miss" | "His past irresponsible financial decisions included buying BMh couldn't afford using student loan money his master's degree pay it parents now monitored spending habits giving him small allowance from own paycheck.
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Dating Nightmares: Weird Things Men Have Done On First Dates

If 2020 has taught us anything, it's that no matter how bad things seem, they can always get worse. This sentiment can also be applied to the sh*t show that is modern dating. You may think you have been on some bad dates, but they can only be worse! We teamed up with The Single Society to show you exactly how awful this sh*t show can be. Here are some examples of the weirdest things guys have done on a first date!

Weirdest Things guys Have Done On First Dates - thumbnail pop art image of man and woman in car would you mind blowing my... breathalyzer | My date had a breathalyzer installed in his car because he had several DUIs. He assured me he would be able to drive, but when he wasn't he asked me to blow into it so his car would start
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My Dating Nightmare: The Cappuccino Cheapskate

No one likes a cheapskate, but unfortunately, there seems to be a plethora of penny pinchers in the modern dating scene. Don't get us wrong, dating can get expensive and frugality is certainly an admirable attribute, but when someone goes to unusually great lengths to save a buck it can be somewhat...strange. But alas! These tightwads make for some of the most entertaining bad date stories and we have teamed up with The Single Society to share them with the masses. If YOU have a great story, please share it HERE for a chance to be featured!

awkward dating nightmare of guy who was a total cheapskate - thumbnail includes pop art pic of woman holding coffee text - if you can't afford coffee, you can't afford this W.A.P | Jeff suggested we meet at one particular establishment you may or may not have heard of. Starbucks.
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Dating Nightmares: Craziest Things Men Have Admitted On First Dates

Let's be real. We all have our flaws. A first date, however, is not exactly the best time to shine a blazing spotlight on these flaws OR unfortunate emotional baggage. Putting the best version of yourself is usually the way to go when meeting a potential mate for the first time, but apparently...some people didn't get that memo. On the other hand, perhaps it's best to let those red flags fly high in order to avoid any unpleasant surprises in the future. Whatever way you look at it, here is a list of the craziest things men have admitted on a first date.

craziest things men admitted to women on a first date - thumbnail pop art image of man eating "Is being a sex addict a deal breaker?" "Oh and I'm broke" "Also I'm still married" | Was on Hinge date guy when admitted was way behind child support about get wages garnished spent 10k boob implants for ex girlfriend
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My Dating Nightmare: Guy Snooped Through My Diary After Awful Sex

One night stands can be a rather enjoyable pastime to an otherwise lonely evening. However, sometimes they don't go quite as planned, and spending the night at home with your cat would have been a far superior decision than lying naked next to a stranger after an awkward session of pleasureless 'love' making. But what good is a trainwreck sex story if no one is there to hear it?! That is why we teamed up with The Single Society to bring you these gloriously terrible dating mishaps such as this one, about a total creeper with absolutely no boundaries or manners to speak of. Enjoy!

pop art illustration of man smiling | THANKS FOR THE SEX EXCUSE ME WHILE I SNOOP AROUND YOUR PERSONAL BELONGINGS got out of shower Jack standing over dining room table where had my note pads Turns out he read my therapy journal
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Dating Nightmares: 14 Texts From Men Who Reacted Terribly To Rejection

Rejection is a hard pill for anyone to swallow, but it is an inevitable part of the dating game. It helps to have a thick skin and a lot of resilience to keep putting yourself out there and accept that not everyone will like you. The key to rejection is taking it gracefully, wishing the other person all the best, and moving on. But unfortunately, not everyone can do that; some people react horribly to rejection and lash out at the person who rejected them. Together with The Single Society, we bring you 14 times men reacted terribly to rejection, and they are truly shocking. Scroll through and be amazed (or not) at the fragility of these male egos!

pop art illustration of guy yelling | not interested in me?! good because you're fat and ugly
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My Dating Nightmare: Guy Was A Boob-Grabbing Creep

Touching a woman inappropriately, or touching her without consent is a crime and should be taken extremely seriously. Unsolicited contact can constitute sexual assault, which, unfortunately, is something that women have to deal with on the daily. It makes dating a dangerous game because you never know what sort of creeps are lurking on the other end of your dating app and for every great guy, there are ten weirdos out there. Together with The Single Society, we bring you this story of a boob-grabbing creeper, who is an awful human being. We feel bad laughing because it sounds like a truly horrific experience. Maybe it's nervous laughter, but God. Help. Us. All! 

pop art illustration of woman pointing | BUYING A WOMAN DRINKS DOES NOT MEAN you ARE ENTITLED TO HER BODY
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