“Hilariously Awkward”: 37 Things Window Cleaners Didn’t Expect To See While On The Job

Once while cleaning a high rise apartment, an old lady kindly ask me if I was hungry and proceeded to open her window and hand me a pizza slice.

So I sat there, 27 stories up, tangling on my chair and eating pizza.

It was a good day.

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, 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 ( I think it was the landlord but can’t remember) got back to him and told him that she 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 name Pumpkin.

Edit: For those that asked for a picture of the dog, this is a recent enough one. Dog Tax - Here is Pumpkin.

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.

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 to not 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 who’s windows were slowly being hidden by the years of “collections”
- a famous footballer who was NOT with his wife - not long after this the company were asked to sign NDA’s.

His favourite?

- a dog breeder (Okay breeder not the right word, someone who had 2 litters) and every 4 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.

Edit - dog tax - meet Holly

okay guys heres a couple more pics of Holly

The footballer was Rooney. He was doing it while his wife was pregnant.

Ive 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.

Edit: 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.

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.

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 3 feet away from a groaning elephant like naked lady.

Despite the pain I laughed.

Not a skyscraper window washer but was a janitor who had to wash the windows in a 6 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 an 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.

I was cleaning windows for this old couple in the apt building where I worked.

He’s telling us how great is it when we come every spring. He loves when all the windows are out at once, it opens up the whole apt, the air flow, bla bla bla...

And, not that we don’t do a great job, but these windows are old and no matter how good 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.

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.

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.

Edit: 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 looks and smells bad.

It was a normal morning and I had just began 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.

Not a window cleaner, but my therapist and I meet at her office in a skyrise, and we've begun this weird tradition of stopping everything we're doing, even if I'm like in the middle of crying or something, and just smile 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.

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 peoples work stations you can see that almost no one works, most people are on Facebook, YouTube or on news sites. But the second the 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.

This is more on the sad side: We clean senior homes and in the dementia ward there was a woman that was asking me why they turned the volume down in the room because she couldn’t hear me. She went on for awhile 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.

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.

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.

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 Maori guy who proceeded to throw the tire over his shoulder and wander off whistling as if nothing had happened.

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 lead 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.

When i was a cleaner there was a old lady who had me do her windows. In the corner of the windiw on her third floor was this massive tarantula that was completely loose and just chillin. When I told her about it she said her nephew was "supposed to fix her spider issue".