I don't know about most painful, but my dad bought a phone many months ago and last week, he wanted to know how to turn on the flashlight on it. I was ready to edit the notification dropdown or give a five step explainer or whatever.

Turns out, nope, you just pull down the notification bar and there's a pretty obvious flashlight button right there. The problem is, you see, he did not know you could drag down the notification bar. There were dozens of notifications there.

I really cannot blame him either. I don't know what UX designer came up with just putting a bar at the top and expecting users to know that you can drag on it. But yeah, still, ouch.

The forgetting everything I took the time to explain even after “dumbing it down” to the simplest terms. Can’t blame them too much as it’s age related, but frustrating nonetheless.

Refusal to use a password manager. They write down the passwords plaintext in a physical pad. Not awful, all things considered, but then write down the password alphabetically without maintaining consistency in naming. Say it’s a password for a streaming service on a Sony TV. It might be under Sony, TV, or the name of the service; and all three titles might be entered in the pad because they couldn’t remember what they’d written it down under the first time. Then had to reset it and wrote it down under something else. So now you have passwords for TV, Sony, and Service, guess which one is right? Heaven help you if there’s more than one Sony TV in the house or something. At least the password managers go by website and a user created name so you have two chances of finding it.

When offering help over the phone they click or tap the wrong thing that leads to an incorrect page or menu, swearing they did it right, and being unable to locate the thing I’m telling them to look for after I led them step-by-step to the correct solution. This one’s pretty infuriating when many menus look the same and my questions about what they’re looking at only gets generic enough responses that I think they’re in the right place. It’s often only corrected when I ask them to take a pic with their phone and send it to me so I can figure out how they f’d up. I ended up installing remote desktop apps on their computers eventually so I could just do the work myself, quickly, with far less fuss.

When I found out that my dad doesn't know what the backspace key does on the PC keyboard. His whole life he's only ever used the Del key and always positions the cursor to the left of text he wants to delete. He used to work at IBM for over 30 years and learned to program back in the day when computer code was printed on punch cards. But I'm pretty sure keyboards already had the backspace key back then.

I had to text my mom a screenshot of the browser menu with the 'share' button circled so she could share a link to me of the website she called me to help her use

Trying to get my elderly mother to understand the difference between wifi and mobile data. Maddening.

I cannot tell you how many times I've had to help family members and friends "fix the sound" on their computers because they somehow changed their default audio output device without knowing it. I really wish people would just check their audio settings when they have a problem with it, instead of calling me to help every time.

I've got a stubborn father. Years ago, back when our old family computer was working and was something we actually used, all I wanted to do was remove a simple toolbar from the single web browser we all used that might have been caused by a virus (probably caused by me being dumb) and uninstall something that caused it (also probably caused by my idiocy). This was around 2019.

The problem was my parents didn't want me on it all night so they had something like an admin password, but I figured it out long before this because they wrote it down in a notebook. The other problem is they didn't know I knew the password, so I didn't wanna let them know I knew it. Also, with the computer being in the living room, I couldn't just fix this at any point because my parents (at least one of them) were usually in the living room at any given time besides at night.

In the end, it pretty much devolved into me telling my father that I'm just trying to remove something that could actively harm our PC, but he refused to let me do it. Don't know if it was because he didn't wanna type the password or what, but it was a short shit show... until he finally relented and for a measly few seconds he had to enter a password instead of spending minutes fighting me on this.

"C'mon you guys! There it is right in front of you the whole time. You're dereferencing a null pointer! Open your eyes!"

my parents are too tech savvy :/
But in school i removed a gum paper from the disk drive with a screw taped to the end of a brush if that counts

They needed me to help them because the Flash drive "wasn't working". They ended up shoving it in backwards and completely destroying the port. I asked why they did it and they said it wouldn't go in.

My cousin was way older than I so his kids were my age. He brought his laptop over because it was showing weird porn ads at very odd times. I usually charge a bottle of alcohol and then throw a big party with that alcohol because I was the go to guy for the neightborhood. Anyway, the porn he was watching was really intense and not at all what you think of as "normal" porn. So I told him everything I found and he said his 15 year old grandson borrowed it when ever he came over. I was genuinly scared of that kid from that moment on. Clown porn was the lighter side of what I saw.

What's the start button? Every time I say click: they don't know if it's left or right.

my dad once asked me to copy files from his desktop to his disk, and then double and triple asked me if he can now delete the files on his desktop safely

you'd think he'd have had copying files figured out after a decade of owning a laptop, but alas