30 Old People vs Technology Fails That Keep Getting Worse

Updated on January 22, 2026

Old people vs technology is the most reliable comedy genre on the internet because it’s never mean on purpose. It’s just pure confusion meeting a screen that offers zero emotional support. And suddenly someone is using Facebook like it’s a town hall meeting, a search bar like it’s a diary, and the block button like it’s a legal document.

If you’ve ever watched a relative fight with their phone like it owes them money, you already know the vibe. These are the funniest internet fails, senior moments online, and accidental tech support requests that make you laugh… then immediately check on your own parents.

Old People vs Technology Moments That Need Tech Support

The “supportive” tweet where Maureen tells Denise she looks dreadful might be the most devastating backhanded compliment ever posted. It’s the old people vs technology equivalent of accidentally hitting someone with your car and saying, “All my love!” afterward. She meant well. The words did not.

Then we’ve got the one-star review furious about hamburgers… at Goodwill. Sir. That is a thrift store. The owner responding “We don’t sell hamburgers” is the calmest handling of an internet fail I’ve ever seen. If I ran that Goodwill, I’d have mailed him a single sock out of spite.

The formal Facebook message announcing she’s blocking Harold is also incredible. “I need 1 or 2 hours to recover” reads like she’s filing paperwork with HR. Old people vs technology is so funny because they treat online interactions like they’re being notarized.

But the undefeated champion here is Edith Jackson accidentally tweeting “nigel farage hot pics” instead of searching it. The panic thread that follows is the purest example of senior moments online: she tries to explain, she makes it worse, she clarifies “weather hot,” and the internet watches her dig the hole deeper with a spoon. A tragic masterpiece.

Honorable mention: the festive Facebook background announcing a birthday, Covid, and a respiratory infection all at once. Nothing says “HOE HOE HOE” like medical trauma shared publicly in glitter font.

And the Netflix profile name turned into a sticky note—“Jean i was watching the Crown”—is honestly innovative. It’s passive-aggressive, efficient, and somehow the most relatable technology hack on the list. That’s not a profile. That’s an emotional memo.

Finally, the chlamydia vs salmonella typo about raw chicken. There are typos, and then there are criminal acts against language. That one belongs in a hall of fame with a warning label.

If this made you laugh and then immediately want to set your phone down gently, go cleanse your brain with 24 Grandparent Memes That Restore Faith in Humanity, 35 Cursed Images That Shouldn’t Exist, and 35 Funny Fashion Choices That Fail With Style.

Mike Hartley writes like a dad watching someone try to print a PDF, sighing loudly, and still offering to help.