33 Awkward And Unexpected Things People Saw While Cleaning Windows
I live in Chicago, but I’ve never lived higher than the third floor. A few of my friends live in fancy high-rise buildings, and it’s a different lifestyle. For starters, I have to clean my own windows. They have people who show up outside theirs, which sounds convenient until you remember you might be standing there in your underwear.
When I’m at a friend’s place, there’s a nonzero chance a window cleaner will suddenly appear outside. Any sense of privacy on the 18th floor goes right out the window. Pun intended.
I’ve always wondered what window cleaners must see when they have no choice but to look inside. These stories pretty much confirmed my suspicions. They’re funny, awkward, occasionally shocking, and sometimes surprisingly sweet. The view isn’t always better from up there, but it’s rarely boring.
1. Lunch With A View
“Once while cleaning a high-rise apartment, an old lady kindly asked me if I was hungry and proceeded to open her window and hand me a pizza slice.
So I sat there, 27 stories up, dangling on my chair and eating pizza.
It was a good day.”
2. A Friendship That Led To A New Home For Pumpkin
“Not me, but my uncle has been doing it for years and had many weird encounters, but this one is kinda sad.
Having changed companies, he started at this new apartment building. Near the top there was this old lady with a dog. The dog was young enough and was always excited to see him. Eventually he started talking to this woman when he was working through a small window, and they became somewhat friends.
Then one day, almost a year on the job, he went up and for the first time the apartment was empty except for the dog, which he found odd. So when he was finished up, he tried to check and see if she was in but got no reply.
A day later, a member of staff from the apartment block got back to him and told him that she had passed away and that she had no family. Assuming that my uncle knew her, the landlord asked about the dog, seeing if there was anything that could be done. My uncle, being the kind fella he was, took the dog.
Nearly ten years later, my uncle still has the dog, a little terrier named Pumpkin.”
3. A Phone Number Against The Glass Turned Into 60 Years Of Marriage
“My grandfather met my grandma while working as a window washer. He put his phone number right up against the glass of her office and hoped she wrote it down.
She did and called, and they’ve been married for 60 years.”
— Anonymous
4. The Best Part Of The Route Was Watching The Puppies Grow Up
“My uncle has been doing this job over 20 years, so I’ve had a few weird stories off him:
- A sign on a window asking them not to clean the bathroom window. Obviously not knowing which window was to what room, they went about their jobs. The bathroom had skinned rabbits hung up.
- A hoarder whose windows were slowly being hidden by the years of ‘collections.’
His favourite?
A dog breeder, okay, breeder’s not the right word, someone who had two litters. Every four weeks he went back to clean the building and got to see the pups growing up.
When he went back and they were roughly 12 weeks, there was one pup left. He asked for her, and now he’s got a rottie called Holly.”
5. Uncut Money, A Sarcophagus, And Some Very Excited Pets
“I’ve been a rope access window cleaner for a couple years and have seen my fair share of weirdness. A couple incidents that stick out are:
- A young couple having fun that invited me to join.
- An apartment in a ritzy building completely empty other than a table with several sheets of freshly printed, uncut $100 bills.
- A real mummy sarcophagus.
Animals were always my favorite, though. Cats and puppies lose their minds seeing you outside their window and will happily chase your mop and squeegee while you work. Always brightened the day.
Another memorable moment was causing a mild panic in the dining room of a local retirement home dementia ward. We felt bad and went as quickly as we could, but the nurses laughing as they tried to contain the pandemonium made us feel slightly better.”
6. The Window Tint Was Doing Less Than Expected
“Not a skyscraper cleaner, but the person on the other side of the window.
I was using a single-occupancy restroom on the 22nd floor of a building that had a floor-to-ceiling glass window along the side of the toilet. Weird, I know.
Anyways, I was wearing a romper, so sitting there in just a bra, with my romper around my ankles. I saw the window washer and was a little startled but thought the windows were tinted, it was fine.
Alas, we accidentally made eye contact as I was standing up to wipe. Clearly tinting does not work up close.”
7. An Unexpected Visitor During Labor
“When I was in hospital in labour with my daughter, I look up from lying over the bed, massive belly, moaning, and what do I see? A window washer!
The funniest thing was that the windows were reflective and he clearly couldn’t see me, or if he could, he was a world champion poker player. He had no idea he was three feet away from a groaning elephant-like naked lady.
Despite the pain, I laughed.”
8. An Uncomfortable Staring Contest With The CEO
“Not a skyscraper window washer, but I was a janitor who had to wash the windows in a six-story building as part of my job, so I used a mix of ladders and rappelling down from the roof with a harness to clean the outside windows.
One day I was washing the outside windows on the executive floor where all the bosses and higher-up employees had their offices.
I was done with one window, so I moved to the next window and looked in and saw the CEO of the company snorting something in his office with the door locked and the lights off.
He looked up and saw me in the window, and we made uncomfortable eye contact for about 15 seconds. Then I just pretended I saw nothing and kept washing the windows.
Never spoke a word about it to him or anyone in the office, but the last day I worked there, he gave me a farewell card with 200 bucks in it and a free solar-powered portable phone charger that the company produced and sold.”
9. The Windows Were A Little Too Clean
“I was cleaning windows for this old couple in the apartment building where I worked.
He’s telling us how great it is when we come every spring. He loves when all the windows are out at once. It opens up the whole apartment, the airflow, blah blah blah.
And, not that we don’t do a great job, but these windows are old, and no matter how well we clean, there’s nothing quite like nothing between you and the outside.
And then he went to stick his head out to look down and squarely smacked his full face into the clean window.”
10. Management Somehow Made It More Awkward
“A friend was fresh out of the shower, sitting at her computer desk undressed, when the window cleaners were at her place.
She heard a noise, so she turned around to see two men outside her third-story window. So she screams and runs into the bathroom to hide.
Later she calls the building management to complain, and they tell her that a notice went out and she must not have seen it.
Then building management decided to ask the window cleaning service to send those guys to her apartment to knock on the door and apologize to her.
Hilariously awkward.”
11. Please Stop Kissing Public Windows
“I am a window cleaner, but not high-rise. The thing I can never understand is when I see lip prints where people have ‘kissed’ the glass in public buildings.
People, if you saw what I clean off of those every week, you would never touch the glass, especially not with your lips.
Since a lot of people are asking, when the glass is super dirty, it’s usually grease, old condiments, bird poop, salt from the sidewalks, winter in Colorado. And a lot of the time I can’t even tell what it is. I just know it looks and smells bad.”
12. The Blinds Went Up On A Cricket Legend
“It was a normal morning and I had just begun cleaning windows. I’m cleaning one with the blind down, not really paying attention.
I realise that the blind is slowly rising, and when it finishes opening, I see him.
Cricket legend Brett Lee doing yoga.
Will never forget that day.”
13. Therapy Takes A Brief Break For A Staring Contest
“Not a window cleaner, but my therapist and I meet at her office in a high-rise, and we’ve begun this weird tradition of stopping everything we’re doing, even if I’m in the middle of crying or something, and just smiling these huge creepy smiles while trying not to blink as the guy washes the windows.
He loses it and starts laughing before he gets to the end every time, and then waves bye at us, and we resume whatever it is we were talking about.”
14. The Window Cleaner Is Not Your Supervisor
“Not as exciting as the other stories, but something I’m blown away by when I’m on ropes is how many people feel guilty about not working when I’m around.
When you look into people’s workstations, you can see that almost no one works. Most people are on Facebook, YouTube, or news sites. But the second they notice me outside the window, they quickly switch to an Excel spreadsheet.
Like they think I’m some kind of productivity spy about to rat them out to management. Keep cruising the internet, people. Don’t mind me!
And also, pointing to the window and saying ‘you missed a spot’ isn’t funny.”
15. A Difficult Moment At A Senior Home
“This is more on the sad side: We clean senior homes, and in the dementia ward there was a woman who was asking me why they turned the volume down in the room because she couldn’t hear me.
She went on for a while about that and how she disapproves of it. Eventually she started calling me Brian and said, ‘Brian, it’s been so long since I’ve seen you. You never come visit.’
I’ve got to say that was both the weirdest and most saddening thing I have seen.”
16. An Early-Morning Office Jump Scare
“Not a window cleaner, but there was one time the people cleaned the windows of the office where I worked very early in the morning when no one was expecting it.
The squeegee or brush thing hit the glass really loudly, and everyone jumped. I half fell off my chair, and one person spilled her coffee.
I’m sure the guy was amused.”
17. Apparently, The Red Overalls Were Working
“What I got was a LOT of flirting.
I don’t know if the pane of glass gave them a sense of safety, or if lots of office chicks are just bored, or if our red overalls were particularly fetching, but something brought out the bachelorette instinct. Notes pressed against the glass, pretend lesbian performances, you name it.
Only seemed to happen when there was a group of ladies, though.”
18. Sometimes The Strangest View Is Down On The Street
“My uncle is a former window cleaner, and he said his most memorable moments were when he lived and worked in Rotorua, which at the time was the crime capital of New Zealand.
The most bizarre was when he saw some naked guy, obviously high on something, getting Benny Hill chased up and down a street by the police.
The second most bizarre was when he heard a crash, followed by a van tire bouncing down the street that was being chased by a massive Māori guy who proceeded to throw the tire over his shoulder and wander off whistling as if nothing had happened.”
19. A Very Slow Exit From An Awkward Situation
“I used to live in a high-rise condo. Sometimes the window cleaners go up the side of the building where my small bathroom window is.
One Saturday morning after a crazy night out, I opened up the window and sat down on my toilet, hungover, with my eyes closed, thinking about where I went wrong in my life choices that led me to this moment.
Then I hear my window close. Apparently the window cleaner needed to close it to go up higher.
Cue the slow ascent of their window elevator thing. They saw me destroying my toilet. We made eye contact, and I gave him the universal ‘nod’ of understanding.
He gave me one back and continued his slow ascent upwards at like an inch a second.”
20. “Supposed To Fix Her Spider Issue” Is An Alarming Sentence
“When I was a cleaner, there was an old lady who had me do her windows.
In the corner of the window on her third floor was this massive tarantula that was completely loose and just chilling.
When I told her about it, she said her nephew was ‘supposed to fix her spider issue.’”
21. The Holes In The Tower Had A Concerning Explanation
“Used to work on cell phone towers on the prairies.
Got to the top of a roughly 250-foot tower once and started to find holes in the metal. I looked into the distance and saw a shooting range nearby. They were bullet holes.
There were people on the range at the time, so I got out of there pretty fast.”
22. They Could Definitely See You
“I was visiting my grandparents in a high-rise, looking out their windows a few stories up.
As the window cleaners went by, I happily watched them clean, hands folded behind my back, because the windows were a one-way type thing where they were basically mirrors from the outside in.
I knew this because I’d seen the building from the outside.
Unbeknownst to me, the level of reflectivity changes pretty drastically depending on the time of day, and I realized that when the window cleaners were going by, they had to wash the windows while some weirdo, me, stood about 12 inches from the window watching their form.”
23. The Blinds Opened On A Startling Scene
“Well, I was washing the outside of the windows at the group home I work at. The state was coming by later that week, and I was super bored.
I walk up to one of my dudes’ bedroom windows to wash it off, and apparently he hears me outside somehow, even though he had his radio turned up to about nine thousand, like he always does.
He rips up his blinds, totes bare, and starts slapping himself repeatedly in the forehead and screaming.
This was pretty normal for him, but it’s definitely the strangest thing I’ve ever seen so far in my life while washing a window.”
24. The Spiders Were Getting Evicted
“My medical school is eight floors. There would be huge spiders outside every window.
We were in small group and kept hearing this loud smack that we couldn’t figure out.
The window washer came into view, and he obviously was not a huge spider fan and was smacking all of them.
Easily 30 large spiders on each window.”
25. A Three-Martini Lunch Turned Into A Conversation Through The Glass
“Not a window cleaner, but had a funny experience.
While consulting at an ad agency in NY, they gave me a sweet office to use on the 25th floor for the six months I was there.
I had just come back from a three-martini lunch with some of the execs and the client. I’m sitting in my Aeron chair trying to fight the food coma and three martinis. I decided to lean back, unbuckle my pants, and loosen up my belt.
My desk is at a 45-degree angle facing away from the exterior windows. After getting into the most lazy and comfortable position in the Aeron chair, I swivel towards the window and see two window washers smiling and laughing.
One guy wrote on a notepad, ‘I’ll have what you had. Where did you go?’ We had a back-and-forth conversation for a few minutes by writing messages on notepads.
The CCO knocks on my office door. I had completely forgotten about our scheduled meeting. He comes in and sees me, belt and pants unbuckled, with the two window washers, and just mutters, ‘Am I interrupting anything?’
I explain the whole thing to him, and the window washers are laughing the entire time. They see him laughing and write, ‘All cool?’
Then the CCO proceeds to pick up a Sharpie and notepad to join in. Everyone was having such a great time, he invited the window washers to lunch on us.”
26. The Water Coming Off The Glass Was Yellow
“It wasn’t a high-rise, but I used to be a residential window washer, and sometimes clients would want the inside cleaned in addition to the outside.
First worst was a morbidly obese man who was living at home, I believe on hospice care, but definitely at least with a full-time nurse.
The man chain-smoked inside his house nonstop. When we cleaned the inside, the water was yellow coming off the glass.”
27. The Job Interview Came With A Fake Family Connection
“One time in college, I answered a help wanted ad for a window cleaner. I thought it was going to be one of these high-rise jobs.
Instead, when I showed up for the interview, it was some methy-looking guy in a parking lot.
I spent the day with him going from house to house cleaning people’s windows. He told me to pretend I was his nephew, and he kept introducing me to customers that way.
He chewed tobacco and, while driving, would spit the juice between his legs onto the floor of his ratty truck.
Then at the end of the day, he told me it was just an audition and tried not to pay me.
One of the strangest days of my life.”
28. Pumping At Work Came With An Unexpected Audience
“Not what I saw, but who saw me.
I had just come back from maternity leave and needed to pump. My supervisor offered up her office. I didn’t even think about closing the blinds because we were on the 22nd floor.
I was sitting on the floor because I needed to be close to an outlet. I was just about finished when I noticed cables moving outside the window and saw the top of a man’s head.
Anyone who’s needed to pump knows how important getting every last drop of that milk is.
I didn’t know what to do, so I stood up and faced the opposite wall, trying to get my bra up and deal with two bottles of milk!
I never turned around. I was so embarrassed. I unhooked my pump, put my top back on, and capped my breast milk.
I got everything cleaned up without turning around, so I have no idea what this person looked like or how they responded to seeing me trying to get dressed, get my pump dealt with, and not spill any milk!”
29. That Window Can Wait
“Dropped in on a dude throwing kitchen knives at a dartboard in an undersized pink robe.
Skipped that window.”
30. Every Painting In The House Was Covered
“Once I was doing this two-story house, with big square plates of glass pretty much everywhere.
The guy had every single painting on his walls covered with sheets and absolutely would not allow us inside to get to the double-hung windows on the second floor.”
— Anonymous
31. The Cleaner Had A Front-Row Seat
“Not a skyscraper window cleaner, but I can speak on behalf of one who was there when someone in my dad’s office accidentally let a bouncy ball hit the window and then proceeded to walk into the window when he got up and reached for it, right when the cleaner was there.”
— Anonymous
32. A Ladder, A Small Kitchen, And One Poorly Secured Towel
“There was this house I used to clean, front and back windows.
Anyway, they had an extension built on the side of their house and didn’t want us climbing on the roof to get to the back in case we cracked any of their tiles.
The lady who lives there, must have been in her thirties, asked if it would be possible to carry the ladder through the house and into the back the next time hers was due to be cleaned. I agreed.
Two weeks later, I knock after cleaning her front windows, and she answers in nothing but a towel. She tells me that she was just about to get in the shower.
I ask if she wants me to leave it until next time, but she says, ‘No, come through.’
So I awkwardly begin manoeuvring my ladder through and manage to make it into the kitchen. As I’m standing, it becomes apparent that her kitchen layout is too small for me to get the ladder through to the back door, but she begins trying to help me.
Which results in, what I’m sure you’re expecting, her towel dropping.
She catches it in the nick of time before anything below the waist is revealed. To her credit, it was good reflexes.”
33. An Encounter That Reinforced The Decision To Quit Smoking
“I used to be the janitor at a busy McDonald’s next to a university campus a while back. Early in the morning, I usually cleaned the windows outside before the drive-through started to get too busy.
Usually saw some fairly strange people, but one that stuck out was a very unkempt and definitely hungover man foraging for cigarette butts in the trash and on the pavement.
After he gathered a handful, he sat on the curb nearby, crushed the tiny bits of old stale tobacco out of the butts into a rolling paper, which he then licked, rolled, and then asked me if I had a light.
If I hadn’t already quit smoking before then, that encounter would have made me do it.”
— u/Vuldyn