These classic Boomer selfie fails are both hilarious and painfully relatable.

There’s something both endearing and excruciating about watching Boomers try to master the art of the selfie. They’ve conquered dial-up internet, navigated the rise of smartphones, and maybe even joined Instagram—but angles and filters? Still a mystery. You’ve probably seen the evidence: noses too close to the lens, faces half-cut off, or that iconic deer-in-the-headlights look. And while these moments are usually harmless and hilarious, they’re also just plain awkward.
It’s like their thumbs are too big and their patience too thin for this particular form of self-expression. But hey, they’re trying—and we love them for it. Still, that doesn’t mean we can’t laugh a little (okay, a lot) at the selfie slip-ups that fill their photo galleries. These cringey captures aren’t just funny—they’re proof that sometimes, age and wisdom don’t help you find your light.