20+ Exasperated tech savvy people share the most computer illiterate individuals they've ever encountered: 'Send both files in one email, so you don't have to pay twice'

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Brad Dickson • Managing Editor
Apr 24, 2024 6:00 PM EDT

There was a certain point in time in the not-so-distant past when plenty of people had never encountered a "Personal Computer" before—a time when listing your basic typing and computer skills on a CV would make you a strong candidate for a varying degree of roles and not raise eyebrows. At this time, it was perfectly understandable when you encountered someone, particularly someone older, who had no way of conceptualizing what the darn thing was, resulting in a degree of bizarrely hilarious interactions as people struggled to come to grips with this wondrous new machine. 

Nowadays, Windows 95 is almost 30 years old—and thus, the widespread establishment of the Personal Computer (PC) in people's homes happened some time ago… So there's really not all that much of an excuse when you don't know how to use a mouse and keyboard. But technology has progressed since, and it's only a matter of time before there's something new that all of us can't get our heads around—and it's just not going to come in the form of something we anticipate.

Yet, where there is the possibility of something in this world, there's someone fulfilling the prophecy of probability. These tech-savvy persons gathered in this online community to share their stories about the most computer-illiterate people they had ever encountered, making for a good collection of relevant tales. 

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  • 01
    "What's the worst case of computer illiteracy you've seen?"
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  • 02
    MrWaffles42 My mom was trying to move ~200 pictures from one folder to another. Her approach was to open one picture, do Save As, save it to the other folder, and then delete the original. One by one. When I tried to explain that she could click-and-drag the whole thing over in two seconds, she said "that wouldn't be any faster than the way I do it!" She would also "save" pictures she found online by copying them, opening Microsoft Word, pasting it in there, and saving it as a .docx file. And sh
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  • 03
    oblong_cheesecake I recently tried explaining how to select multiple files to a co-worker and said "click and drag" and she had no idea what that meant. She is only 40. This same person thought turning off the monitor was the same as turning off the computer. Edit to add: this person uses a computer at work every day and has for years. 2.1k Reply Share • • •
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  • 04
    VictoriaEuphoria99 I was helping someone with a website for their small business. I told them I put an "alt" tag on some of the photos that would show text when they put their mouse over it, and to try it out. He literally picked up his mouse and placed it on the screen. I fell on the floor and almost myself. 3.1k Reply Share • • •
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  • 05
    Loftzins The instructions said to close the door... but it meant the latch on the floppy drive for the Commodore 64. My buddy got up and closed the door to the room. 2.6k Reply Share
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  • 06
    Professional_Gaping The whole family has used emails for years, the other day I had to send one for my dad, and he said something in the line of "send both files in one email, so you don't have to pay twice". 2.4k Reply Share • • •
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  • 07
    mildOrWILD65 My mother refused to believe that calling her granddaughter in Ireland, using Whatsapp, over their home wifi, was not the same as placing an international phone call and that it would cost "an arm and a leg" if she did that and "we aren't made out of money, you know!" 1.4k Reply Share
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  • 08
    Elvish Mystical I knew someone who once put their credit card in the floppy disk drive to make an online purchase. 2.4k Reply Share • • •
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  • 09
    launderingpileofcash A middle aged lady got frightened after being told she needs a mouse to operate a computer. (This was early 2000s) 2.1k Reply Share
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  • 10
    Silent_Ad_8672 I work in a call centre, and one of my jobs is helping the call centre clients with basic computer troubleshooting. It is..an interesting task trying to explain to a man who makes more than I do and has been working the same job since longer than I've been alive where and what the start button is. 1.8k Reply Share
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    psychkp I was once trying to teach someone how Windows Explorer worked. For whatever reason, they could not grasp the concept of using folders to store documents. I had to get an actual folder and piece of paper out to demonstrate putting paper into the folder before she was able to grasp the concept. 1.6k Reply Share ...
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  • 12
    outcastspice My employer hired someone to work for me doing tech support. In the first few days I had to show her how to open Outlook, create a new email, where to put the recipient address, etc. Had to show her multiple times how to open Excel, let alone use it. She never did get the hang of email, eventually we concluded she actually couldn't read and we had to let her go. This was in the early 2000's and she was probably in her 30's at the time. 1.3k Reply Share
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  • 13
    a_burdie_from_hell My grandfather typed "big bbs" as his facebook status like, 15 times in a 5 minute span... I think I understand what he was trying to do... 928 Reply Share
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  • 14
    MrSpindles I worked at the head office of a major UK company. They hired a woman as a website administrator and, on her first day of training, asked her to click on something. She just stared blankly, and they repeated, click on it with the mouse. The what? Was her reply. They had interviewed her for the job and it turned out that in 2004 she had somehow never used a computer that had a mouse. I don't think she made it past lunchtime. 792 Reply Share
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  • 15
    BeepBopARebop This just happened last Friday. I am a new legal secretary in a small law firm where the partners have been in business for 50 years. Part of my job is to print every email that comes in and of course people always send big fat attachments Friday at 4:55.I had some emails queued up to print and since it was already 10 minutes after I was supposed to be gone I asked the managing partner if he would shut down the computer after it finished printing. He did not know how to shut down a
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  • 16
    ZeldaFan812 "Will my laptop still work if I take it upstairs?" 719⇓ Reply Share KeyLog256 I did have an Asus laptop about eight years ago which was great, lasted like a workhorse, was getting on for a decade old itself. It had to be always on and plugged in though. If you unplugged it, it would turn off, and there's a good chance it wouldn't turn on again. 362 Reply Share • • •
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  • 17
    ArizonaGeek I worked for a law firm, and one of the administrators would print the PDF of the case from her email. She would then scan it back to her computer because it "downloaded to the documents folder so she could move to the case folder." I told her she could just click the down arrow and download it, then move the file, saving hundreds of sheets of paper. She said that was too complicated. She only lasted a few months before she was fired.
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  • 18
    40_degree_rain Growing up in the 90s, I remember seeing multiple adults try to yell commands at a computer screen. They didn't understand about standard I/O like keyboards and mice because their only concept of computers was from watching Star Trek. 688 ⇓ Reply Share
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  • 19
    Eternally_anxious92 My roommate got a prebuilt gaming PC and when setting it up she spent 45 minutes getting frustrated trying to find the HDMI port her monitor plugged into... It had a port cover on it from shipping. It took me 30 seconds to find. She argues with her boyfriend her discord nickname "Boomer" is inaccurate, I disagree. 679 Reply Share ...
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  • 20
    tristanjones We got my grandma a computer so she could get emails with pictures of her grandkids. It had a sleep mode button and have with a cover for the monitor. She diligently would put it to sleep every night and place the cover over it. Sincerely thinking it needed rest and the lights out. 645 Reply Share tacwombat This is very sweet. 267 Reply Share
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  • 21
    Humpie Douglas I've been working in IT for almost 25 years. A few weeks ago I had a user tell me their second monitor wasn't working. I walked over and pressed the power button. Problem solved. IT would be a great career if it wasn't for the users. 499 Reply Share
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  • 22
    Skarth Sold a computer on craigslist about 10 years ago. Keyboard, mouse, LCD monitor, and cables. He took it home, and said it didn't work, the screen would stay blank when he powered it on. When he brought it back, he was pressing the power button on the LCD monitor, not the computer. 409 Reply Share
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  • 23
    BobFX My sister places every file she creates on the desktop. She does not understand folders. She cannot move a window around on the screen, she cannot resize a window except by the minimize and restore buttons in the upper right corner. She does not understand if she is using Google and wants to change to a different search she does not have to close and reopen Google but can use tabs. 374 Reply Share
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  • 24
    Cuddles_McRampage Last year there was a new employee with a CS degree who said they didn't know how to use Word and wanted to do everything with Adobe instead. This is at a government agency, so redoing all the systems to accommodate one person was definitely not happening. 300 ⇓ Reply Share . . .
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  • 25
    Attitude AdjusterSE I once had someone who thought their Wi-Fi was down because their wireless mouse had run out of battery and needed new ones, think that's my favourite. 280 ⇓ Reply Share
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  • 26
    OptionalGuacamole I'm a graphic designer and it's fairly routine for me to be emailed photos taked with a phone of a webpage displayed on the customer's laptop or desktop monitor. They don't know any of the myriad ways to take a screenshot or copy a url. Some of them can't send an email from a desktop OS. I'm a late GenX and I know I should be used to it by now, but the inability of people younger than me to do anything that isn't on a mobile device continually boggles my mind. Bonus: If you cla
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  • 27
    sovietarmyfan I am studying for a IT education. Some students in my class are just unbelievable. We are supposed to learn a lot of stuff like python programming, using virtual machines, set up networks etc. But a lot of students almost fully rely on chatgpt to do stuff for them. They don't learn at all. 159 Reply Share
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  • 28
    Keefer1970 During a late 90s "PC training" session at my job, I was in a room full of older employees who'd apparently never even seen a computer before, much less used one. When the instructor asked us to click on something with the mouse, one guy picked up the mouse and pointed it at the monitor like a TV remote, and then asked the instructor why it wasn't doing anything. 143 Reply Share • • •
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  • 29
    SmiteIke This was 10+ years ago. Anytime the house WiFi wasn't working well, my roommate would unplug the Ethernet cable from the modem and the router and hold it up and down (like you would hold a hose to drain the water out) to "let the electrons drain out" so the internet wouldn't be clogged. I tried to explain this wasn't how Ethernet worked but he said the cable technician told him to do this, and that was the end of the matter. The thing is it usually worked because it reset the internet c
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