Awkward

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My Dating Nightmare: Man-Child ONLY Spoke About Race Cars, Then Threw Insults At Me

Together with The Single Society, we're back with yet another hilariously awkward dating fail. This time, meet Aaron, the self-obsessed man-child, who could ONLY speak about race cars. And if you've ever been on a date with a guy who wouldn't STFU about himself (so, probably all of you!) then you'll relate to this latest tale of dating debauchery the most.

pop art illustration of guy at desk dreaming about a car - funny story about bad date and how he didn't stop talking about race cars "He wouldn't shut. the. F*CK. UP about race cars. He was looking for a woman to support his passion by taking on all financial responsibilities and give up on having kids. All for his budding racing career."
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My Dating Nightmare: Guy Was A Compulsive Liar, Still Living At His Parents

Let's face it, we've all told one or two white lies on a date to make ourselves seem a little more impressive than we really are. But there's a big difference between a white lie and a straight-up gigantic untruth. That, if I'm not mistaken, is called compulsive lying. Not cool guys, not cool. 

Together with The Single Society, we bring you this latest online dating horror story about a compulsive liar from Connecticut who was nothing like he appeared on Tinder... 

pop art illustration of guy in car - funny story about bad date and all the things he lied about | "He spoke about his debilitating ADHD, his dates with several women who went to rehab for alcohol abuse, and how he has never left the country, and has ZERO desire to so."
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My Dating Nightmare: Real Women Reveal Discoveries Of Ex's Cheating

Finding out that your boyfriend or husband has been cheating on you is devastating, whatever the circumstances. But sometimes, the truth is so ridiculously stupid, that it's almost funny. Maybe. Sort of. 

Together with The Single Society, we bring you funny, cringe-worthy, and ridiculous stories from real women who discovered that their exes were cheating on them. From finding out he's sleeping with your boss's sister, to meeting their other girlfriend while you're both bailing him out of jail, these stories will make you cringe on behalf of these pathetic men. Enjoy!

real women reveal ex's cheating stories - cover pic woman describing husband cheating o valentines day | For Valentine's Day, my husband gave me a nice card. The only problem was he accidentally gave me the one intended for his mistress. I filed for divorce that week. IT'S NOT CONSIDERED CREATING IF you ARE A SEX ADDICT
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Awkward Texts That Were Sent To Parents By Mistake

Everyone knows and can relate to the anxiety caused by sending a text to the wrong person. Whether it's to your boss, an ex-boyfriend, or sending a text about someone to that person by mistake, these slip-ups can cause a mini heart-attack each time. But perhaps the worst is when you send a text to your parents containing some sort of sexually explicit message that was clearly meant for someone else. The stress that causes, is another level, and reading through these texts can give you a taste of just how bad some kids have put their foot in it. 

awkward texts that kids sent to their parents by mistake | Mom Edit If my family asks just say are my roommate can't deal with this coming out right now. Ok so would like pretend didn't see And continue pretending not know always known since were 5? Well wasn't supposed happen. Can't wait meet roommate xoxoxoxo Omg mom stop | Daddy Contact Read 12:45 AM Did mean send this Answer phone NOW Are serious Is this is do whole at School
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My Dating Nightmare: Guy's 40-Year-Old Roommate Saw Me Naked

As many of you can attest, one-night stands can be awkward at the best of times. But when your hookup of choice's roommate shares his bedroom with another guy, you've got yourself a whole new level of uncomfortable morning chit-chat. Welcome to the latest in our series of hilarious, horrible, and awkward real-life dating stories from women currently navigating the world of online dating in New York City.

pop art illustration about awkwardness of NYC one-night stand - funny story about guy's roommate seeing her naked in the morning | IT'S BEEN TOO LONG SINCE I FELT MORTIFYING REGRET OF A ONE NIGHT STAND l woke up and found myself standing completely naked in front of a strange man almost equally as exposed as I was save for his tighty whities sleeping on the futon.
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Redditors Reveal: People Whose Parents Walked In On Them Having Sex

There are a few things you definitely don't want your parents catching you doing, especially when you're a teenager. Watching porn and doing drugs are a few of the things that come to mind, but the worst thing in the world for your parents to walk in on? Yep, you guessed it. Having sex. There's not really any coming back from your parents walking in on you doing the dirty (think American Pie) and you just have to accept that things will never be normal again. These Redditors reveal just how awkward things got when their parents caught them mid romp and we're cringing so hard for these poor individuals. Read on and you'll see what I mean...

redditors reveal what happened when their parents walked in on them having sex - cover pic not my parents but her parents. I yelled out loud "we were westling". Very awkwar
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My Dating Nightmare: Real Women Reveal Their Crazy Summer Hookups

Most of us have had a summer romance or two, filled with drunken nights on the beach, sex under the stars, and inevitable raging hangovers the next morning. There's something about being abroad that brings out the adventurous side of us all, making us do things we would never do back home and giving us memories that will last forever. vacation hookups are the best, and the memories they leave us with usually last forever. There's something about being abroad that brings out the adventurous side in us all, and together with The Single Society, we bring you stories from real women who told us their craziest summer hookup accounts, sex and all. 

women reveal crazy summer hookups - cover image “While camping in a remote area on the Great Wall of China, I hit it off with a guy. We wandered off by ourselves, one thing led to another and before I knew it I was bent over. Yes, I had sex on the Great Wall of China.”
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Worst Things People Experienced During Sex

Sex is great when it goes smoothly. But sometimes something really awkward can happen and totally kill the moment, making you wish the ground would swallow you up. Usually, we keep those stories to ourselves, so they die with us, but these people have bravely revealed the true stories of the worst things that happened to them during sex. They're making us cringe so much, we feel sorry for them. Scroll through and feel their pain! 

real stories of the worst things people experienced during sex - cover image while having sex an elderly woman asked if we were ok
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My Nightmare Date Put My Number Online For Strangers To Send Me Inappropriate Pics

We've all had bad dating experiences, but has your story ever been published as a blog? Together with The Single Society, we're bringing you tales of shocking dating disasters from real women living in New York City. From the ridiculous to the cringe-worthy, to the depressingly obscene, we've got it all. So if you think you've had a bad date before, buckle up and read on because this one really takes the cake. 

story about bad online dating fails - cover image woman describes how she received inappropriate pics after number was posted on Craigslist and doxxed | "l began receiving an overwhelming amount of d*ck pics from unknown numbers. Someone had posted an ad on Craigslist with my phone number saying I was down to f*ck tonight."
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My Dating Nightmare: Guy Bailed, Then Licked My Face ON PURPOSE

Dating can be fun — after all, meeting new people, discovering new places to eat, seeing the sites of your city are objectively all good things. But as we all know, dating can also be a total sh*tshow, and anyone who has navigated the world of online dating can attest to having to kiss many a weird/ creepy/ rude/ f*ckboy frog before finding their prince. But with each frog comes an entertaining story, and together with The Single Society, we bring you the latest tale of hilarious, horrible, and awkward real-life stories from women in New York City currently navigating the world of online dating.

story about bad online dating fails - cover image woman describes guy who tried to kiss her and then licked her face | "Craig went in for a kiss. I awkwardly turned my head. He came in for what I thought was another kiss...Then slowly ran his tongue right up my nose. I could feel his wet slobber drench my face."
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Florists Reveal Worst Card Messages They've Had To Deliver With Flowers

Flowers are the perfect gesture for almost any occasion. Whether it's to celebrate a birthday, an anniversary, the birth of a new baby, or to offer condolences, flowers are the easiest gift to send someone. Of course, the essential part of your floral delivery is the card, which expresses the sentiment with which you sent the flowers, and is usually left to the florist to write out. Typically, the messages read, "I love you," "I'm sorry for your loss," or "congratulations". But other times, they reveal the downright awkward and messy situations that people get themselves into. Reddit asked florists to reveal the most outrageous card messages they've had to deliver with flowers, and they are genuinely shocking and reveal the messy details of some people's lives!

funny messages florists had to write on cards with flowers - reddit post sorry I knocked up your friend | xelo_pyke 808 points 10 hours ago My fiancee is florist. She often sends ridiculous messages she's been asked attach flower orders. My personal favorite so far Sorry knocked up friend David."
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My Dating Nightmare: Guy Was A Broke, Recovering Porn Addict

Dating isn't exactly a walk in the park and for every rare great date you have, there's always a plethora of bad dates to balance it out. We've all been there and everyone can recall a really bad date. Together with The Single Society, we bring you the worst of the digital dating era and feature stories from real women who are navigating the minefield of dating apps in New York City. This one's about a recovering pornography addict and it's a porn-NO thank you from us!

woman reveals bad date about guy with porn addiction cover image guy dragging bag of baggage | AND THAT IS HOW I ENDED up BROKE AND IN THERAPY! "He disclosed how his debilitating addiction to porn had caused him to lose his job and ultimately ruin his life."
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My Dating Nightmare: Dude Lived In A Minivan And Asked To Shower At My Place

The trials and tribulations of dating in New York is a never-ending storybook of awkward and hilarious. Together with The Single Society, we bring you some of those stories from real women in NYC in their attempt to navigate their way through finding love in the digital era. We embrace the good, the bad, and the downright ugly of modern dating, but also get some laughs along the way. So pull up a chair, grab a glass of wine, and enjoy this woeful tale of dating debauchery. 

woman reveals bad date about guy who lived in minivan and wanted to use her shower cover image of man asking woman to use her shower | IT WAS LOVELY MEETING you CAN PLEASE USE YOUR SHOWER?
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Girl Misunderstands Insurance Agent’s Request For Car Pics, Sends Pics Of Herself Instead

Being able to laugh at your own mistakes is a great quality to have. It helps to not take yourself too seriously in life, especially when there's potential for major embarrassment. Alyssa Stringfellow had this exact attitude when she was asked by her agent to send her "a picture straight on and a picture taken from each side", which she did... of herself. Her agent emailed back pointing out her mistake and thankfully she saw the funny side and posted the story on her Facebook which quickly went viral. Check it out below and have a laugh!  

girl misunderstands what insurance agent means when he asks for pics | Sometime midmorning following day (today *hem hem check my email and find THIS response Hi Alyssa am going need pictures like just took, except needs be vehicle As can see didn't send pictures my car sent him pictures myself
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My Dating Nightmare: Sexually Graphic Mailman Was A Total Mood Killer

Welcome to the latest from our dating blog — The Single Society — where we bring you the real-life hilarious horrible and awkward online dating stories from women in New York City. Finding romance in this day and age is never an easy thing but navigating the minefield of dating apps is a journey in and of itself. Dodging douchebags has turned into a sport for eligible women everywhere, but when you have a bad story that's too good not to share, that's where we come in. Enjoy this shocking tale of true modern dating debauchery.

dating nightmare mailman sexually graphic mood killer bad dates great stories dating apps funny single society New York City | comic cartoon woman holding a finger to her lips you EVER MEET A MAN AND IT'S SO OBVIOUS THAT NO ONE HAS EVER TOW HIM TO SHUT THE F*CK UP?
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The Awkward Faces Synchronized Swimmers Make

Synchronized swimming is a beautiful sport. Between the moves, the teamwork, the colors, and the synchronization, it is truly an art form and a sight to behold. But another side to synchronized swimming is the funny faces that the athletes make while they are performing. It might be beautiful to watch, but it requires a lot of energy, which doesn't always translate into beautiful faces. Scroll through these pics and have a giggle at the close-ups of the awkward faces of synchronized swimming. 

awkward Faces Synchronized Swimmers funny pics swimming face pool
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