Skyscraper window cleaners are often overlooked, unless you're paying for their services or are one of them, suspended 20 floors up. They work behind the scenes, leaving dirty windows spotless. But their unique perspective means they've seen things most people keep private. From office shenanigans to bizarre bedroom views, these workers have witnessed it all. And now, they're sharing their strangest, funniest, and weirdest on-the-job stories on Reddit. The takeaway? If you live or work in a skyscraper, consider investing in curtains or blinds – or take a glance out the window to check for an unexpected audience.
About this list
- 1
From Redditor /u/FerryPencer:
I saw a man and a woman squirting water out of their mouths at each other. They were probably highballs, not water, but I could not see what they had in their glasses.
First, he took a swallow and squirted it all over her. Then she did it to him—they took turns. You should have seen them. They were hysterical the whole time; it seemed like the funniest thing that ever happened.
0 - 2
From Redditor /u/A_Window_Cleaner:
Working windows right out of high school, I cleaned the suite windows at the Wynn where Prince Harry stayed.
I found myself cleaning royal vomit off the balcony window.
The prince knows how to throw a good party.
0 - 3
From Redditor /u/differt:
[I saw] a guy threw kitchen knives at a dartboard while wearing an undersized pink robe.
I skipped that window.
0 - 4
From Redditor /u/darkerthanmysoul:
My uncle has done this job for over 20 years, so I have a few odd stories from him:
His favorite?
0 - 5
From Redditor /u/nowaynotever:
Five years ago, four window-cleaning lowlifes worked on a neighboring building rooftop. They prepared ropes that morning in a tall apartment suburb of Australia.
One of the most beautiful womenI have ever seen put on lingerie. When she finished pulling up and attaching her stockings, she spotted us across the road gawking.
Casually, while keeping eye contact, she pulled the blind down to her shoulders to cover her face and continued putting on makeup.
It was one of the best days of my career, and I will love that woman forever. It was not strange, but I wanted to share a nice memory with you all.
0 - 6
From Redditor /u/zerothed:
Ex-skyscraper window cleaner here, but in Hong Kong.
Skyscrapers now have "fire floors" built in, like every fifteenth floor where the whole floor is empty: no walls, no windows, as if someone forgot to build a floor there. They are just pillars. They serve a purpose: if fire starts, it will not spread past that floor.
People in the building I worked at used that empty floor for strange things. Some practiced music. Some ate lunch there (it has a nice sea view). Also, some thought no one would see them [get intimate] if they did it behind a pillar.
We never paid much attention to anything on that floor. It is just funny when they acted well and properly, not knowing we were lowering down from above, having heard them from two floors up. I do not know why people did it. Everyone who worked in that building knew we cleaned windows daily. Perhaps they could not hold back any longer...
Seeing them on that floor was always funny. Two guys stared at them, hanging forty floors off the ground. I always loved seeing their faces twist when they spotted us watching them.
0 - 7
From Redditor /u/PivotPIVOTPIVOOOT:
My ex, a high-rise window cleaner, always talked about what women did. He said the glass gave them security. Women flashed and pressed their chests against it. They mooned and pressed their bottoms against the glass. They wrote phone numbers and pressed them against the glass.
During our engagement, he held up his ring finger, pointing to his ring. He wore an engagement ring. Some women did not stop this. He said it made some women try harder.
0 - 8
Redditor /u/t3khole:
Three of us dropped near each other. One person enjoyed messing with people inside. This was a twenty-five story dorm. Near the building's midpoint, you could start swinging. He yelled at me and the other guy to swing over to him. A college girl lay passed out on the window sill during his drop.
He said, “On the count of three, slam your suction cup on the glass and scream.”
We scared the girl. She fell off the sill right away. Everyone laughed. She took a selfie with us. Later, she met us at the bottom of the building and playfully punched all of us. She had a good spirit.
0 - 9
Redditor /u/sirmcchris:
I worked for my stepdad's company. They used sketchy equipment. There was no safety rope or vest to stop people from falling to certain ends or getting permanent injury. We used stack ladders. These are hard to put together without upper body strength.
You need someone at the bottom holding you if you stack three or more ladders. Sudden strong winds will make you regret every choice you made. This dangerous setup is the craziest part of this story.
I stacked six ladders and cleaned a third-story window at a private place. As soon as I climbed up the ladder and reached the window, I scared a parrot in a cage on the other side. This damn parrot let out a shriek that scared me because I did not see the parrot first.
I felt nervous being three stories up on a shaky ladder. I almost fell backward. I hugged the ladder and had to go down because I was so shaken. Going down, I was nervous, but I have done it easily before. Once you get used to it, you only get scared if an unexpected parrot screams at you.
0 - 10
Redditor /u/dman2316:
I was not a skyscraper window washer. I was a janitor who washed windows in a six-story building for my job. I used ladders and rappelled down from the roof with a harness to clean the outside windows.
I washed the outside windows on the executive floor. All the bosses and higher-up employees had offices. I finished one window. I moved to the next. I looked in. I saw the company CEO snorting something in his office. The door was locked. The lights were off.
He looked up. He saw me in the window. We held uncomfortable eye contact for fifteen seconds. I just acted like I saw nothing. I kept washing the windows. I never said anything to him or anyone in the office. The last day I worked there, he gave me a farewell card. It held two hundred dollars and a free solar-powered portable phone charger the company made and sold.
0 - 11
Redditor /u/normal242:
It was a normal morning. I just started cleaning windows. I cleaned one with the blind down. I did not pay much attention.
I saw the blind slowly rise. When it opened, I saw him: cricket legend Brett Lee doing yoga. I will never forget that day.
0 - 12
From Redditor /u/mehfara:
I cleaned a skyscraper where I know almost everyone who works there.
I saw a job interviewer being intimate with another guy. This other guy was probably someone he interviewed. The interviewer, who is straight, married, and has kids, gave me $500 not to tell anyone.
This was the easiest money I ever made.
0 - 13
From Redditor /u/sdelly:
My boyfriend does a lot of high-rise window washing.
A man walked into an office while he was working. He unzipped his pants. He proceeded to pee into a potted plant. He walked back out as soon as he finished.
The man had no idea he had an audience.
0 - 14
From Redditor /u/Zakmcj17:
I work for my dad's window cleaning business in Scotland. While cleaning a couple's windows (a ground-floor bungalow), I saw the couple getting intimate in the living room. They made eye contact with me and did not stop.
This was probably the most awkward experience of my life. But you better believe I finished the job and took my twenty pounds tip.
0 - 15
From Redditor /u/THEEHaydenRush:
Every time I cleaned this man's apartment window, he and his friend watched weird adult movies on his huge TV.
They watched it like they were watching the news.
0 - 16
From Redditor /u/ThinkDontPray:
What gets me is the number of people who throw syringes off buildings.
The ninety-two-story building in my city has them scattered everywhere.
0
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