Dating Nightmares: Horrific Halloween Walk of Shame Stories

  • The Awkward Uber Journey Home


    I went home with this guy after a Halloween party. I woke up and put my slutty schoolgirl outfit back on. I had mascara smeared all over my face and my pigtails had seen better days. I was trying to sneak out without being seen by any of his roommates seeing me so I ordered an Uber and thankfully the uber seemed to be right by their apartment complex so I ran out to meet him. Then one of the roommates came down and got in his car. Turns out, he was my f*cking Uber driver. We didn't know each other and I just got in the backseat and sat there awkwardly while he drove me 30 minutes back to my place.

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  • The Park Bench Pineapple

    Hair - BSEGIFS

    After some post-Halloween party fun with this guy I was hooking up with, I was completely hungover and miserable. I was dressed as a pineapple and was headed back to my car desperate to get home. There just so happened to be a kids' Halloween parade on the street where my car was parked and all the roads were blocked off. I asked a police officer if he could remove the barricade so I could leave but he said I had to wait. So I wanted there on a park bench, hungover as hell, for three f*cking hours, dressed as a pineapple with fishnet stockings while hundreds of kids frolicked down the street.

  • The Sephora Stopover


    I ended up crashing with a guy after a Halloween party and was dressed as a pirate wench. I was all the way across town and my best friend had her 30th birthday brunch that morning and there was NO way I was going to make it if I went home to change. I made a pit stop in Sephora to touch up my make up then I rolled into brunch still fully dressed as a pirate.

  • The Slutty Walk Of Shame

    People - SHAME. SHAME. SHAME.

    I went to a big school down south where everyone dressed to the nines for football games. After a Halloween party, I hooked up with some random dude and had to walk back through campus to my dorm room in a slutty tiger costume in 6-inch stilettos. It didn't help that everyone I passed were all prim and proper sorority girls donning pearls, sundresses, and big hats. Some of the girls in my sorority spotted me and I ended up being completely slut-shamed. I dropped out after that.

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  • The Subway Ride Of Shame

    Joker - HI...

    I went home with a girl one Halloween and woke up with nothing to wear but my costume which was the king from Burger King. I couldn't exactly afford a cab at that point in my life so I got on the subway with everyone wearing their suits and ties….and I was Burger King. When I got off the train I just so happened to run into my ex-girlfriend. It was awkward.

  • The Penis Debacle

    Cheezburger Image 9563685376

    I crashed at a sorority house where I went to school in southern Florida. It was pretty hot that weekend so I only wore a pair of underwear under my costume. I didn't think it would be an issue because I would be going home. I had to walk back to my house still dressed as a giant penis.

  • The Puke Parade

    Cartoon - #Laff

    I was dressed as a gorilla with not much underneath because it was really hot in there. I got hammered and crashed at a girlfriends house. I woke up with dried vomit crusted into the fur of my gorilla costume. Since my ride went home with someone else I had to take a city bus home…as a puke encrusted gorilla.

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  • The Prison Party

    Facial expression - NRAW TAM NOT GOING TO JÂIL!

    I drank entirely too much on Halloween and ended up getting arrested. I spent 14 hours in a holding cell dressed as Little Bo Peep. Complete with the poofy skirty, lacy thigh-high socks, and a curly wig. My mom picked me up after I finally got arraigned the following day. It wasn't pretty.


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