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Dating Nightmares: Women Reveal Real-Life Humiliating First Date Moments

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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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!

  • Naked Nightmare

    Hair - Hair - This whole thing's embarrassing."
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    "I got to my first date with this guy early and decided to run the bathroom. I was wearing a low plunging romper so I couldn't wear a bra. So when I sat down on the toilet I was completely naked. The lock on the bathroom door was a little janky and it was a unisex bathroom. I thought I had it secured but suddenly the bathroom door swung and there was a man on the other side. We were both startled and I slammed the door shut. I walked back into the bar to find the man who had just seen me naked on the toilet was my date."


  • Parent Trap

    Facial expression - Everybody's parents suck. Welcome to reality.
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    "Went home with a guy I was on a first date with. I was living with my parents at this point in time. At one in the morning, someone was furiously banging on his front door. My guy's roommate came in and told me my parents were at the door. They freaked out when they noticed I hadn't come home and when I wouldn't answer my phone they used the Find My iPhone app to come to my 'rescue.'"


  • Girl Vs Glass Door

    Photograph - #YOUNGERTV
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    "I was super excited when this guy I was crushing on asked me on a first date. I put on my cutest dress and sexiest high heels. I got to the restaurant and saw him waiting for me out on the rooftop. I strutted ever so confidently...straight into a glass door. I fell on my ass and blood was gushing everywhere. The whole restaurant heard the 'bang' and was looking at me." 


  • Underwear Surprise

    Hair - BOUNCE
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    "I was on a first date at a bar in the wintertime. I arrived at the bar and was taking off my coat to settled into my seat. I unwrapped my scarf and a pair of lacy white panties fell to the table right in front of him. When I did my laundry the panties got stuck to the wool scarf. Oh! And they were still stained with blood. FML."


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  • Leaking Ostomy Bag

    Hair
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    "While on the first date with this really cute guy I suddenly smelled something foul. Turns out my ostomy bag seal ruptured right in the middle of the evening. I am not sure if he noticed the smell but I bailed before I could find out."



  • Texting Slip-Up

    Hair - ELEMENTOFCRIME
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    "A first date wasn't going so well with a guy I met on Tinder. I texted my best friend under the table to tell her how bored I was and how I would NOT, in fact, be having sex anytime soon. I accidentally sent that text to him."


  • Vomiting Nightmare

    Blond - 07
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    "On a first date, this guy asked if I would like to do a shot of Jameson. Not one to back down from a challenge I agreed. I am really not good at taking shots and this one didn't go down so smoothly. I bent over and vomited all over the bar. I wasn't even drunk, but the manager told me I had to leave."


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  • Period Leak

    Hair - Facial hair - MY GOD THERE'S BLOOD EVERYWHERE
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    "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."


  • Sh*tty Spewing Situation

    Hair - Arm
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    "I was drinking a glass of red wine on the first date with this guy I was really into. He said something funny and I spewed the red wine all over his white shirt."


  • Diarrhea Disaster

    Hair - It smells like wet shit.
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    "We went to dinner and a movie on the first date. I took one bite of my chicken and it tasted somewhat off. I don't like to complain, so I continued eating my meal. A few minutes into the movie my stomach started doing gymnastics. I went to the bathroom 3 times and thought I was in the clear. I settled back in to watch the movie and my stomach started acting up again. I had a little accident in my seat and basically had to tell him I needed to Uber home immediately to deal with this sudden bout of diarrhea."


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  • Cat vs Tampon

    Hair
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    "After a really great first date, I invited the guy back to my apartment. We started kissing and suddenly I see my cat batting something across the living room. My cat dug out a dirty tampon from the garbage can and playing with it."


  • Sleeping Bathroom Blunder

    Hair - Thigh - I TOOK ANAP
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    "I drank a little too much on my first date with this guy that I had met through some friends. I went into the bathroom and sat down on the toilet and I guess I needed a little 'rest.' Suddenly I heard banging on the door and it flew open. Two security guards were standing there with my date. Apparently my little 'nap' went on for 45 minutes and my date was getting worried I was sick or something had happened. Nope. Just fell asleep on the toilet."


  • About the Author

    TheSingleSociety
    Nikki is currently living in NYC with her husband (who she met on Bumble after experiencing the absurdity of online dating) and working in digital marketing. She clearly enjoys recording the ridiculous debauchery that is the modern dating scene. Nikki is also partial to a tall glass of Prosecco, her black/calico kitties, 90s music and playoff hockey. Drop her a line if you have a good story for her to write about.
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About the Author

TheSingleSociety
Nikki is currently living in NYC with her husband (who she met on Bumble after experiencing the absurdity of online dating) and working in digital marketing. She clearly enjoys recording the ridiculous debauchery that is the modern dating scene. Nikki is also partial to a tall glass of Prosecco, her black/calico kitties, 90s music and playoff hockey. Drop her a line if you have a good story for her to write about.