When Boomers Text: 28 Old People Texts That Went Hilariously Wrong
There’s something uniquely funny about old people and their ongoing battle with texting. I’ve been on the receiving end of a few boomer texts myself, and let me tell you, there’s nothing quite like deciphering a message that reads more like a cryptic code than a conversation. Whether it’s accidental emojis, messages sent to the wrong person, or just hilarious misunderstandings, old people texts are comedy gold. In this collection, we’ve gathered 28 of the funniest boomer text fails that are sure to make you appreciate how far we’ve come with texting… and maybe remind you to double-check your own messages before hitting send.
Boomers may have mastered the art of phone calls, but texting? Not so much. From auto-correct disasters to total misunderstandings, these screenshots capture the funny side of the generational tech gap. It’s a parade of confusing abbreviations, random emojis, and messages that completely miss the mark. Whether it’s a grandma mistaking a kiss emoji for a cookie or a grandpa sending a group text to the wrong people, every text is a delightful reminder that even the smallest tasks can become a challenge in the digital age.
Whether you’re looking to laugh at a classic “mom text” or see a dad’s struggle with group messaging, this collection is a reminder that some things—like texting—just don’t come easily to everyone. And let's face it, their confusion makes it all the more entertaining.
After squinting at your phone through these old people texts, you’ve probably had a good laugh at the generational divide when it comes to texting. You’ve seen everything from misunderstood emojis to accidentally hilarious autocorrects, all of which capture the funnier side of boomer communication in the digital age.
If these old people texts cracked you up, there’s plenty more where that came from. Check out our other meme galleries for even more texting mishaps and elderly social media fails. Whether it’s more hilarious generational differences or just good old-fashioned meme content, we’ve got something to keep you laughing.
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Phil M., Co‑Founder & Content Strategist
Phil is one of Thunder Dungeon’s co‑founders, doubling as our resident meme analyst and dark‑room brainstormer. He specializes in trend‑spotting across social platforms and shapes the editorial calendar to keep our galleries fresh, topical, and worthy of your valuable procrastination.
