21 Unforgettable Cringey Christmas Photos

There’s something about the Holidays that makes people want to document absolutely everything in photos. This isn’t a new phenomenon, though the ability to take many duplicates and filter through them to choose only the best ones to share is still quite new. “Back in my day,” you had to snap the pic and hope for the best. Sometimes you get the perfect family portrait, sometimes you get a big fail. In honor of the most wonderful time of the year, let’s take a trip down memory lane and check out the most wonderfail photos of them all!

  1. Flipping the Christmas Bird

    This little girl slyly flipped the bird while she looked off-camera and grinned. Needless to say, her mom was shocked when she went through the photos later and finally noticed!

  2. This One’s a Handful

    “I’m just now, internally, asking myself, in quite a worried way, if I might have made an error.” – That one TikTok, but also probably this lady.

  3. “My Husband’s Coworker When She Was A Kid”

    I don’t know what’s creepier, the santa, the sepia, or the fact that the woman who shared this has a picture of her husband’s coworker when she was a child??? Wild.

  4. “Our Photographer Sent Us All The Images From Our Holiday Photo Session Including This One And I Love It”

    I am here for the juxtaposition in this one. The absolutely magical winter wonderland backdrop to this kid’s goofy face… just gold!

  5. “Santa, am I on the nice list?” “That Depends.”

    This Santa is sooooo done. But he’s still showing up for work because the children Depend on him. (Okay, I’ll stop now!)

  6. PhotoShop Pop

    “She didn’t like my dad’s not-smiling face so she cut out one from a different picture, pasted it in place and sent it to the printers. Note the glue on my dad’s face where grandma had attempted to affix the smiling face before it shifted during printing. Still one of the funniest things ever sent to more than 200 friends and family.”r

  7. A Tighty Whitey Christmas

    “When I Was A Kid, My Mom, Who Is A Seamstress, Would Make Funky Gifts Every Year For Christmas. Sometime In The Late 80s, She Got Her Hands On Some Giant Men’s Underwear And Made Sports Bra’s Out Of Them. Hence, My Two Aunts And Grandma Modeling Them On Christmas Eve”

  8. Double-Take

    “Being In A Family With Five Children, You Hardly Ever Get A Great Photo With All The Kids. 27 Years Later My Sister Decided We Should Reenact This Photo On The One Day A Year We All Get Together”

  9. The Dog Days of Christmas

    “We Were Taking Our Family Christmas Photo, And Let’s Just Say The Dogs Weren’t In A Holly Jolly Mood. This Photo Was The Worst Of The Batch, But Now It’s A Conversation Starter. We Keep It Right By The Entrance Of Our Home Here In St. Louis”

  10. Basically a Renaissance Painting

    “My Boss, Who Has 6 Kids, Captured Every Sibling Dynamic Possible In One Photo”

  11. Tears of Joy?

    This Was Supposed To Be Our Christmas Card. It Turns Out She Just Hated That Sweater

  12. The Gang’s All Here! And Terrifying!

    “Christmas Was Scary In Yugoslavia”

  13. The ONE Time the Family Did Nothing Wrong.

    “Christmas 2009. We Went To The Mall To Take A Picture With Santa And Seemingly Nothing Went Wrong… My Son Didn’t Cry, The Line Was Manageable But Santa’s Attention Was Focused Elsewhere”

  14. “The Only Baby Picture I Have. Why?”

    Because it’s the only baby picture you will ever need. Amazing!

  15. “This Was The Picture That My Family Sent Out As Our Family Christmas Card Back In ’91”

    I just… I just want to know what the thought process here was.

  16. Too Much Cringe, Too Few Words…

    “The Infamous Christmas Photo Shoot Of 1984. Dad’s Short-Shorts And High Socks Highlighted His Fashion-Forward Attitude And Athleticism; My Sister’s Cheerleading Perfection Revealed Her Vow To Never Look Bad In Any Photo- Ever, And My Single Jazz Hand Stance Complete This Awkward Family Christmas Card From Over 30 Years Ago”

  17. Merry Catmas!

    “My Dad Built This To Protect The Tree From The Cat”

  18. St. Nicholson, Is That You?

    “My Dad On Christmas Morning” “Your dad reminds me of a young Jack Nicholson!”

  19. “Our Awkward Family Swim Team Christmas Photo”

    Like the song says… SWIM AWAY, SWIM AWAY.

  20. Was It Worth It?

    “My Sister And I Thought It Might Be A Good Idea To Have Our Kids’ Photos Taken As A Christmas Present For My Mom. With Two Hungry, Tired Newborn Babies And A Bored 3 Year Old, It Was Quite Possibly The Worst Day Of Our Lives. This Was The Best Pic We Could Get Of All Three Of Them”

  21. Last But Definitely Not Least…

    I just wanna know WHY. WHY WHY WHY to all of it!!!