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My Dating Nightmare: Guy's 40-Year-Old Roommate Saw Me Naked

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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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.

  • Karl didn't get off to a promising start...

    Gadget - I NEED A NEW GUY.
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    My worst one night stand was during a time where I was experiencing both an overactive libido and terribly poor judgment. 

    After chatting with Karl, a burgeoning actor/director/musician/voice over artist/screenwriter barista I decided to grab drinks at a dive bar in close proximity to his apartment…which he shared with several other people…

    All in their 40s. 


  • We got drunk, made out at the bar and decided to take it back to his place.

    Kiss - SNL
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    (As I mentioned, standards were questionable).

    Not long into our little Rendez-Vous we found ourselves 4 PBRs and 2 shots of Jame-O deep and engaged in some considerable heavy petting.  As our conspicuous displays of affection began making our fellow patrons obviously uncomfortable Karl suggested we take things back to his apartment so we could continue our adult fun in private. 


  • His apartment was gross...

    Hair
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    Karl's place was quite the sight to behold, indeed. This garden level apartment was the epitome of a multi-inhabited 'artist' apartment in NYC. The walls were covered in eccentric artwork, it was impossibly cramped and smelled of incense and sweaty feet. 


  • And his bedroom resembled a prison cell.

    Face - WHAT FRESH HELL IS THIS
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    His room measured no more than 8×8 and consisted of his bed lofted upon a rickety-looking wooden structure with an equally questionable ladder leaned up against it. A dirty hole-ridden futon and a 'desk' propped up on some cinder blocks sat in the space beneath the bunked bed. 


  • The sex was mediocre at best.

    Red - 5 You'se the Worst
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    We also had to walk through his other roommate's room in order to get to his.

    This is what I get for f*cking mildly-employed thespians.

    After some relatively mediocre sexy time (better than no sexy time, I suppose) in his hazardous bunk bed we passed out rather quickly. 


  • The next morning, I attempted to get out of there ASAP.

    Photo caption - Excuse me, I have to go and vomit.
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    I woke up around 7 AM and wanted to expeditiously make my exit before I contracted any more serious diseases from his greasy bed linens.

    I made my descent down the feeble ladder in search of my clothing. 


  • An (almost) naked man appeared in the room. It wasn't Karl.

    Face - (WHe Who are you?
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    When I reached the floor my eyes finally adjusted. I 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. 

    His eyes opened, and I freaked. the. F*CK. out.

    "AHHH! OMG!" I screamed, causing Karl to spring from his deep slumber. 


  • It was his roommate. Literally. FML!

    Cartoon - I NEED TO MAKE BETTER CHOICES ABOUT THE PEOPLE I SLEEP WITH
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    "Sorry man," he said through the door. I didn't realize you had anyone over."

    Turns out, he and this guy didn't just share an apartment…they shared a room.

    I never reconnected with Karl, and I have since improved my decision-making skills. 


  • 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.