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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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Funny, Brutal Letters Of Disappointment From Girls To Their “Exes” (September 17, 2020)

When it comes to dating, it's a harsh world out there. There are tens of psychos, weirdos, and freaks to sift through for every normal guy you meet, and it's natural to get deflated when you waste your time one of these idiots. After a bad experience, they say that journaling can be a therapeutic way of releasing any negative feelings you may hold towards a person. And what better way to do that than via a public journal of shame that the disappointing man in question may see? Or, at least, his mom. Together with To The Guys I've (Kinda) Dated — an Instagram account by and for women, containing letters that frustrated women have penned to the disappointing guys they've dated — we're back with another collection of letters. They're just as funny as the last lot, so scroll through and enjoy.

funny letters of disappointment from women to the guys they've dated | thumbnail includes two letters Text - Dearest Josh, Thanks for calling me 74 times in 46 minutes after I said I wanted to take it slow....and then blaming it all on your daughter. The 3 minute voicemail was real cute too. Please lose my number. Thanks, Angela
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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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Funny, Brutal Letters Of Disappointment From Girls To Their “Exes” (September 11, 2020)

Have you ever been on a hilarious, horrific, or cringe-worthy date? We assume the answer is yes, because, well, who hasn't? How nice would it have been to tell the douchebag in the question exactly what you thought of him? Of course, some women choose to dish out a harsh truth after an awful date, but it's not worth the emotional energy for others. Because let's face it - a man taking constructive criticism post-date? Hard to imagine. We've teamed up with To The Guys I've (Kinda) Dated - An Instagram account created by women, for women, who submit letters containing all the things they've always wanted to say to the disappointing men they've dated. Scroll through this week's haul and then check out last week's in case you missed them.

letters of disappointment from women to guys they've dated | text - Dear Dre, Awesome been sticking over year but can't accept my Facebook friend request. Find new FWB. Love Jenna
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Awful Profile Pictures From Russian Dating Sites

Recently, we covered the eight profile pics women really need to stop using on dating apps. From duck face selfies to pictures with exotic animals, they're all as bad as each other. But nothing, and I mean nothing, can prepare you for the ridiculously weird profile pictures that Russians use on dating sites. As you scroll through these pictures, you'll cringe on behalf of the people posting them, and feel sorry for the people who have to swipe on them. Honestly, they are too much!

Awful Profile Pictures From Russian Dating Sites | woman tied to a bed with sausages | woman posing with a chicken
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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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Funny, Brutal Letters Of Disappointment From Girls To Their “Exes” (September 3, 2020)

In case you didn't catch the first two segments of our new series, we've teamed up with the popular Instagram account, To The Guys I've (Kinda) Dated. Together, we bring you a weekly collection of letters that women have written to the sorry excuses of men they dated. From the long term boyfriends to the one-or-two-date guys, these are the words of disappointment that women wish they could have said in person, for fear of them falling on deaf ears. Instead, they put them out to the universe (AKA, on Instagram), and maybe, just maybe, the guys will read them there, do some soul searching and change their ways. Unlikely though. Anyway, here are the latest letters for you to look through and chuckle at, and here are last week's just in case you missed them.



letters of disappointment from women to guys they've dated | Dear James, Every morning get up use bathroom very quietly pretend l'm still asleep so can masturbate before get back bed. Yes, sometimes have quickie, however, 30 seconds pumping doesn't work Lots things are hard life, but orgasms shouldn't be Love, Layla GUYS Kinda DATED | Dear David could overlook fact didn't look anything like pictures on Bumble. However couldn't overlook side hustle involved taking other peoples' bikes and selling
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Profile Pics Women Shouldn't Use On Dating Apps: Tips And Tricks

In the digital dating era, finding a meaningful relationship behind the screen of your smartphone can be an undoubtedly daunting task. With the overwhelming plethora of dating apps and profiles men and women have to siphon through at any given time, it is particularly difficult to make a solid impression. In the quest to garner attraction from the opposite sex, many women in this generation have fallen victim to the horrible disease that is being basic as f*ck, and quite frankly, the madness needs to stop. Together with The Single Society, we bring you the 8 profile pictures women really need to stop using on dating apps—in our humble opinions. 

profile pictures women shouldn't use on dating apps - cover pic pop art woman taking selfie making a duck face "this sexy duck face is sure to find me a quality man" The epidemic duck face unfortunately taken over planet. Girls think they appear playful and sexy, but reality, comes off slightly desperate attention seeking
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Funny, Brutal Letters Of Disappointment From Girls To Their “Exes” (August 31, 2020)

We've teamed up with the popular Instagram account, To The Guys I've (Kinda) Dated, who publish funny and real letters of disappointment from girls to their "exes." Together, we bring you a weekly collection of messages women have submitted about the freak-shows they dated, expressing all the things they wish they could have said to them. From the guys who take your virginity and don't call you back, to the creeps who flirt with your mom, men find new and creative ways to disappoint each time. Scroll through this week's hilarious letters and then check out last week's, just in case you missed them.


letters of disappointment from women to guys they've dated - cover pic letters about man taking woman's virginity and not calling her back, and man who sleeps with hot roommate | Ben, Thanks taking my virginity at age 27 and then breaking up with right after s not like saving someone special or anything. Sincerely, Lo GUYS Kinda DATED | Dear James sorry stopped calling back after finding out and hot roommate share bed, even though have two extra rooms. Please stop sending nudes. Best, Alexandra
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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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Woman Live-Tweets Hiding Poop In Purse Because Date's Toilet Wouldn't Flush

Picture the scene; you're back at a guy's house after a great date, and you feel confident enough to poop in his toilet. No big deal, right? Right. Except, his toilet doesn't flush, and now you're left staring at a big ol' turd floating in his toilet while he waits for you in the other room ready for some sexy time. You want to die. What do you do? If you're Canadian-based Makela St. Fort, you come to the obvious conclusion that there's nothing to do except picking it up, wrapping it in toilet paper, and sticking it in your purse. And finally, live-tweet the whole thing. In disbelief? So was I, until I read the sh*tty ordeal below. Enjoy!

woman tweets about putting poop in purse on date because guy's toilet didn't flush | misunderstood worm @_blotty Following Him so beautiful moment smiled at ,u had s really sweet my head have piece my poo my purse
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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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