38 Funny Times Boomers Battled Technology And Failed Both Wholesomely And Hilariously

It’s a universal truth that at some point, every youngster becomes an unofficial IT expert for their family elders.

After all, if you’ve ever so much as glanced at a smartphone or laptop, you’re instantly classified as the go-to tech guru in your family’s eyes. And let’s be honest, while our beloved seniors have a wealth of experience and wisdom that far surpasses our own, their tech adventures can sometimes turn into comedy gold.

Pleated-Jeans is diving into the hilariously relatable world of seniors vs. technology. From sending ’email texts’ on their smartphones to mistaking the CD drive for a cup holder, our elders’ tech mishaps are not just funny; they’re a testament to their fearless foray into the digital age.

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3. “You Gonna Need A Bigger Screen”

4. “My Grandma Printed Some Photos From Her Phone”

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6. “My grandpa found a screw on the floor and assumed it fell out of his phone”

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8. “When My Grandma Googles Something She Puts “Please” And “Thank You””

9. “My Girlfriend’s Grandma Thought The Ipad Was A Cutting Board”

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14. “Friend’s Grandma Just Asked Whose Phone This Is”

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16. “My Grandma Called Me Over To Fix Her Computer Because “Everything Moves Backwards””

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26. “My 90 Year Old Grandma From Japan, Showing Us How She Zooms In With An iPhone”

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33. “My Grandma Is Getting Pretty High Tech These Days…”

34. “My Dad Doesn’t Know How To Turn Off This Front Camera Heart Feature On His Phone And He Tried To Send Me A Pic Of His New Stove”

35. “My Nana Asked Me To Fix Her Phone Because “The Outside Clock Is Always Showing The Wrong Time””

36. “My Grandmother Complained Her Remote Was Confusing, So I Grandma-Ified It For Her”

37. “Just Got My Grandma Her First Cordless Phone. Baby Steps”

38. “When Mom Uses Technology”

Jason Mustian

Jason Mustian

Jason is a Webby winning, Short-Award losing humor writer and businessman. He lives in Texas with his amazing wife and four sometimes amazing kids.