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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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Dating Nightmares: 12 Freakiest Things People Asked For 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

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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Dating Nightmares: Dumb Things Guys Said On First Dates

As if dating wasn't hard enough, sometimes men say things on a date that make you wonder if they have any brain cells at all. It seems pretty obvious that on a first date, you should be on your best behavior, which includes not commenting on women's bodies, not being creepy, and not voicing any extreme views you might have. But it seems some guys missed the memo. Together with The Single Society, we bring you a comprehensive list of the absolute dumbest things men have said to women on first dates. Honestly, there's stupid, and then there's these. Enjoy!

Dumb Things Guys Said On First Dates cover pic | pop art pic of man and woman text - “You’re almost 30. I think law school is a bad idea. You are better off finding a husband that makes good money if you want to have kids before it’s too late.”
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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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My Dating Nightmare: Guy Was A Holier-Than-Thou Homophobe

Ever gone on a date with a raging homophobe? If so, you'll know how painfully awkward it is. If not, this woman will walk you through her bad experience, with no details spared. Together with The Single Society, we bring you the latest tale of dating debauchery in NYC, where women attempt to navigate their way through the minefield of lunatics out there, to try and find the one. It's not easy, but hey, at least bad dates make great stories, right?

pop art illustration of man praying - woman describing how guy wanted his wife to be a virgin | "He told me that he prefers his wife to be a virgin, because he feels that a woman should be pure when she gives herself to her husband, or else why wear a white dress? TOGETHER WE CAN PRAY THE AWAY!
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Dating Nightmares: Women Reveal Worst First Dates With Cheapskate Douchebags

Ah, that awkward, age-old debate of who should pay on a first date. Some argue that splitting the bill is best, because hi, welcome to equality. Others believe that chivalry and feminism can peacefully coexist. They maintain that although a woman should always offer to pay her half, men are expected to decline the offer politely and insist on paying. But no one talks about secret option C, where the guy flat-out refuses to pay at all.

Together with The Single Society, we bring you stories from real women who went on dates with total cheap-ass douchebags. From those who refuse to leave a tip to those who try sneaking their own alcohol into bars, these stories reveal the worst type of men to go on a date with. Guys, frugality is not a cute look on a first date. Ladies, have you experienced cheap ass first dates?

stories of first dates with cheapskate douchebags - cover pic pop art pic of man look at empty wallet | l had a date at Starbucks, but when I arrived, the guy was already holding a cup of coffee from McDonald's. He told me Starbucks coffee was too expensive for him, so I had to wait in line to buy myself a coffee.
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Dating Nightmares: Women Reveal Real-Life Humiliating First Date Moments

Going on a first date is nerve-wracking enough, but when you throw in a bout of bad karma, some food poisoning, and a period or two, you're in for a nightmare of an experience. Together with The Single Society, we bring you real-life tales of humiliating moments that women have suffered on first dates, and the cringe factor is next-level sh*t. Honestly, you couldn't make this stuff up!

stories of humiliating first date moments - cover pic pop art image of woman description of getting period blood on white cushions while on date | I met a guy on Bumble and we were having drinks on a couch on a rooftop. I got up to go to the bathroom and I had my period all over the white cushions.
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My Dating Nightmare: Guy Stuffs His Face, Leaving Me Starving

There is a certain unspoken etiquette when it comes to dating, of which most people are aware. From showing up on time to the date and not speaking only about yourself, these are often the things that determine whether or not there will be a second date. But some people have no idea how to conduct themselves on dates, leaving the person on the receiving end totally baffled! When will these guys learn?!

Together with The Single Society, we bring you the latest real horror story of the online dating scene in New York City, and this time it's about a guy who thought a work event was the perfect place for a first date. After eating in front of the poor starving girl, he tried (and failed to get them free food. He sounds like a real keeper, eh?

pop art illustration of man eating burger and story of how he ate a slider without giving it to his hungry date | An acquaintance of Marc's approached us with two delectable sliders on his cocktail napkin. I was salivating. He handed one to Marc, who shoved the entire thing straight into his mouth. Wow, what a gentleman.
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My Dating Nightmare: Guy Was 45 Minutes Late, Then Wouldn't Pay For Drinks

Rule number one when you're on a date is to always keep cool and give a good impression. Even if you're raging inside, never ever EVER show it on the outside. It's not a good look. Rule number two? Don't be a cheapskate. Again, not a good look. 

In our latest tale of dating debacles from real women in NYC, brought to us by The Single Society, it seems like this guy missed both those memos. Big time! The dating world is a tough one, but hey, at least bad dates make good stories, right? 

pop art illustration of guy shaking fist - funny story about guy who argued with manager and brought his own bottle of wine to bar | He argued with the manager, then slipped his bottle of wine under the table cloth, deviously attempting to open it with a miniature pocket knife on his key chain.
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