While helping my mother troubleshoot her phone:

I can’t do anything because the keyboard keeps going away

Everything I click on tries to take me to WalMart

It keeps saying the phone is overheating but it’s not overheating, should I download this program it’s recommending?

No! I didn’t download anything! I don’t download things! Wait… Is the app store considered “downloading”?

I can keep going lol

Fortunately my dad is a retired cybersecurity architect so they live as modern-day Luddites.

Don’t know about most painful, but it definitely sticks out.

My mother screamed for me at the top of her lungs on the other side of the apartment. I hurried into her office, where I see her pointing at the screen saying “FIX IT!” So I look at the screen and… it’s a save dialogue in Word, asking her if she wants to save her document.

Me: It’s asking you if you want to save the document.
Mother: Well how am I supposed to know that?
Me: Do you want to save the document?
M: I DON’T KNOW!!

It’s like she saw the dialogue and her brain crashed. She definitely could’ve read and understood it, but just chose not to. That sort of thing was a frequent occurrence sadly.

Helping my octogenarian mom with her iPhone is the most painful experience. She often calls me about something that has “popped up” in some app that she’s using. I tell her to just close it and she says “how?” I then say something like “just click the OK button … or the Done or Close buttons, that will be some unknown color … or click the X in the upper right or maybe the upper left corner … or click “Done” or “Close” in the toolbar, on the left or right sides … or maybe the thing has slid up from the bottom and you need to swipe down to get rid of it … or maybe you need to click the Home tab on the app’s bottom bar.”

I’ve actually been an iOS mobile developer for 15 years now. Anybody who thinks there’s any sort of consistent, intuitive design principles behind Apple products is insane.

the fact that my grandmother absolutely, hard ass refuses to do anything that would improve her situation. Just bitches and moans and has great big narcissistic pity parties until someone forces it down her fucking throat.

For example, her vision isnt great, she complaints its hard to use the computer cause she cant see to type (Shes one of those chicken peck typers). I tell her to get a large print keyboard with a backlight, it’d be easier for her to see and use.

She says no, it wont help. nothing will help. boo hoo pity me blah blah bullshit.

Long story short, it goes back and forth for a month, with her refusing the idea, refusing when I directly link her to a keyboard to buy (it was cheap, too), etc etc. Just making a big fucking woe is me pity party out of it.

I finally say fuck it, buy the goddamn keyboard myself, take it over to her house, put it on her computer.

within 5 minutes “Why didnt you tell me about this before? Its amazing! I can see it and use the computer again!”

Shes the reason i’ve been balding for 20 years.

I set up my mom on Microsoft Outlook many years ago, back when you had to set the server and so on.

She called me a few days later and said her email wasn’t working, so I walked her through looking at the options, making sure the right addresses and preferences were checked, etc.

After about 45 minutes, I remembered that I already set everything up correctly and it was working. Then I decided to ask, “are you typing the @ symbol, or are you typing the word at in the email address?”

Yep.

Mother in law calls me during work, blaring warnings sounds blaring in the background, warning her that she has a virus and NOT to try to reboot or unplug the computer….

MIL: what do I do/why is this happening?

Me: you clicked on something… unplug the computer

MIL: but it says not to

Me: it’s ok, it is trying to get you to call the number so that you will give them money

MIL: I am too afraid

Me: ok, if you want to give them money or your credentials so that they can take all of your money, feel free. Just don’t drive to Walgreens to buy gift cards again… you will miss your soap operas

MIL: Ok, I’ll unplug it

Friend of the family but still…

Had to travel by boat to an island with no road connection to turn on a printer, after having been promised that it was, in fact, on.

Once turned on it was working. Well as much as a printer can work.

I bought my mother a laptop and she treated the touch pad like something that was to fragile to actually use. So she hardly used the computer because no matter how many times I showed her you could actually press it and move your finger across it and it wouldn’t break and she kept asking me how to move around the desktop using the keys cause “I don’t want to damage it”. I finally got fed up one day and found myself tapping the touch pad really hard repeatedly while saying “See it won’t break!!!” She ended up giving the laptop away cause she was too afraid to break it.

Cave woman that I helped: “You’re not installing porn are you?”

Me: “Uhh, no?! Is that what you meant by helping you to setup the computer. Are you mistaking me for your husband?”

My father is an engineer, which has its ups and downs. He can definitely be trusted to read a dialog box and nearly 100% of the time even understand what it says. Abstract concepts, problems he’s never encountered before, all generally no issue.

My stepmother, however, once asked me if she needs to rewind a DVD before putting it away. We’ve been working on it with her over the years. She’s certainly better now, but she still has an acute case of just randomly clicking on things without reading them.

My parents are generally pretty good with tech. But where I end up pulling my hair out is when I look at my mom’s notifications. She lets any app notify her, and she has lots of apps. The other day when I looked she had two different weather apps reporting the temperature as a non-dismissable notification, and neither one of them was right.

I honestly don’t know how we’re related.

The other thing is when my mom says “but you told me to use this!” I got her to switch to Chrome from Internet Explorer, a dozen years ago. Now when I want to switch her over to Firefox (not even Waterfox!) she says, “but you told me this was the one to use!” Yeah, it was, during the Obama Administration. Same story with LastPass and Bitwarden. Sometimes the best tool changes, mom.

My father is 85, used to be a dev. No issues, maintains his file sync between his two sites by himself via various clouds. Sticks to Windows.

Can’t get him to use proper passwords (as in random generated stuff from his password manager) though, he insists on needlessly peppering the weak-ish passwords he comes up with and storing that in his decent password manager instead. I guess you can’t win them all.

My late mother-in-law’s phone had so much malware running on it that it was completely inoperable. She had poor vision, so would just tap the screen at random to try to get dialog boxes to go away. She didn’t really use ut for anything but making and receiving calls. I booted the phone in safe mode and removed basically everything from it, but it would inevitably reinstall. Eventually, I just factory reset the phone to make it usable again. Then I went through the accessibility options and increased the font size to obnoxiously large so she could read it. She really just needed a dumb phone.

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.