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More Embarrassing Posts By People Born Before 1964

Cringe, confusion, and way too much oversharing.

By Micaela Montaña

Published 3 months ago in Funny

They came. They saw. They accidentally posted it three times. Boomers on the internet are a gift that keeps on giving, whether they meant to or not.


Born before 1964 and typing like the Wi-Fi is on fire, these posts are part confusion, part conviction, and 100% comedy gold. Every click feels like opening a time capsule... that’s been shaken, dropped, and signed “Love, Mom.” They’re not trolling, they’re just trying. And failing. Loudly.


So get ready, clear your cache, and prepare for another round of digital mayhem from the greatest generation to ever mistake Google for Facebook.

  • 1

    Boomer Logic: Millennials Are Babies in Diapers, Still

    Two boomers carrying a full-grown adult in a cartoon stroller. Zero irony.

    Boomer Logic: Millennials Are Babies in Diapers, Still

  • 2

    Vehicle on Fire = Picnic Vibes

    Your mom doesn't know how she posted this nor how to take it down.

    Vehicle on Fire = Picnic Vibes

  • 3

    Bomb Thereat at the Mall, Let’s Party!

    Cartoon woman + cake + terrorism alert = classic Facebook energy.

    Bomb Thereat at the Mall, Let’s Party!

  • 4

    Merry Chrtistmas 🍆

    We don't know if it's a typo... or a threat.

    Merry Chrtistmas 🍆

  • 5

    Google Search (The Facebook Group)

    They think it’s Google. They’re asking it how to boil eggs.

    Google Search (The Facebook Group)

  • 6

    Stephen’s Mom Is Dead! I'm So Glad... I Mean, Sad

    “We had our differences” + cake emoji = emotional whiplash.

    Stephen’s Mom Is Dead! I'm So Glad... I Mean, Sad

  • 7

    Taylor Swift: Satanic Queen of the Night

    According to this post, she’s sacrificing fans between Eras Tour dates.

    Taylor Swift: Satanic Queen of the Night

  • 8

    My Wife Left Me. Here’s a Meme About It

    He’s coping with heartbreak... using Facebook to do it.

    My Wife Left Me. Here’s a Meme About It

  • 9

    Premium Adult Alert: It’s Still Mom’s Job to Fix It

    A text to nephews, a meme from 2014, and a boomer aunt on a roll.

    Premium Adult Alert: It’s Still Mom’s Job to Fix It

  • 10

    This Pink Dolphin Is Definitely Real. Please Clap.

    AI dolphin says hi. And maybe asks for your bank info?

    This Pink Dolphin Is Definitely Real. Please Clap.

  • 11

    Please Share This Obviously Fake Soldier

    AI guy with 7 kids and no soul, and 24k shares by Tuesday.

    Please Share This Obviously Fake Soldier

  • 12

    My Husband’s Dying and It's... LOL?

    “It’s hard to watch” then why post it with a heart-eyed emojis?

    My Husband’s Dying and It's... LOL?

  • 13

    Skipped Church, Got Diarrhea: And Everyone Needs To Know

    A spiritual journey in one Facebook post.

    Skipped Church, Got Diarrhea: And Everyone Needs To Know

  • 14

    Back in My Day, Snow Shoveled Itself!

    When teens don’t clear your driveway and it's obviously a moral failure, not just... winter.

    Back in My Day, Snow Shoveled Itself!

  • 15

    Not All Men… Just the Cringe Ones

    “Some men want trust, not games” and they post about it daily.

    Not All Men… Just the Cringe Ones

  • 16

    Small Plane Hit Roosevelt (Still a Great Day!)

    Caption tone: cheerful. Content: mild national emergency.

    Small Plane Hit Roosevelt (Still a Great Day!)

  • 17

    The Same Battle Of The Generations

    At least my generation doesn't make cringe posts about which generation is better.

    The Same Battle Of The Generations

  • 18

    Boomers Believe Jupiter Is Just… There

    “Wow! Amazing view from Earth tonight!” (It's AI, Carol.)

    Boomers Believe Jupiter Is Just… There

  • 19

    I'm Still Your Mom (Even in AI)

    She's sad, she's cringe, she's making it everyone's problem.

    I'm Still Your Mom (Even in AI)

  • 20

    Phone? Gone. Childhood? Forced.

    Same old story. Those kids found a new way to use their phones.

    Phone? Gone. Childhood? Forced.

  • 21

    Angry Old Man

    The AI makes it cringe, why do boomers say everything through pictures?

    Angry Old Man

  • 22

    Gourmet? No. Childhood Trauma on a Plate? Yes.

    “This generation has no idea” about this ham & cheese horror show.

    Gourmet? No. Childhood Trauma on a Plate? Yes.

  • 23

    Me, My Late Husband, and the Sweet Bread He Loved

    This photo says grief... but also, amazing editing.

    Me, My Late Husband, and the Sweet Bread He Loved

  • 24

    Gen Z: Can’t Start a Revolution or a Lawn Mower

    Boomer AI art strikes again. Two fake people. One fake argument. All too cringe.

    Gen Z: Can’t Start a Revolution or a Lawn Mower

Categories:

Funny Comedy

Tags:

boomers baby boomer cringe posts cringe boomers funny boomers funny posts funny pictures embarrassing pictures embarrassing posts
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