26 Beautifully Awkward Family Christmas Photos That Seemed Like a Great Idea at the Time

Awkward Family Christmas Photos

Gather 'round for a merry dose of awkwardness with 36 family Christmas photos that redefine festive oddity. From awkwardly timed snaps to unintentionally hilarious poses, these candid photos capture the peculiar charm of family gatherings during the holidays. Be prepared to witness everything from unexpected photobombing pets to unintentionally bizarre holiday decorations. Embrace the quirkiness of Yuletide memories!

Our Awkward Family Swim Team Christmas Photo.

Before dad has to go to work.

He looks just like his father.

One year old me, Santa in furry slippers and the most disturbing and scary Befana ever. Italy, 1996 (In Italy the Befana is supposed to be an old, kind woman who delivers gifts to kids on Epiphany eve).

The moment my mom realized I was going to be a handful.

Our Aunt Helen made these for the three of us and while I know she worked very hard on them, I was mortified. That’s me on the left. I’m smiling but my eyes are red from crying because I didn’t want to wear it. The compromise was that I didn’t have to wear the bonnet. I don’t have much of a fashion sense but even then, at a tender young age, I knew this was wrong, very wrong.

Mom, there’s a reason there wasn’t a line to see this Santa

The Santa display was sad, and Santa looks even sadder. I found this pic of me with Santa and couldn’t help but notice the surroundings and his miserable look.

We were trying to create a winter wonderland scene and save money by shooting our own picture. We ended up with almost 90 photos that all looked like this, so we just went with it and this year I got actual requests to post this card.

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.

Me and my parents. December 1992

My memories of meeting Santa are fond ones. I came across this pic, however, and was startled by the look on this particular Santa’s face. He looks a little less interested in what I want for Christmas, and a little more interested in how I’d taste in a stew.

This was supposed to be our Christmas card. It turns out she just hated that sweater.

This is the 2006 Christmas Card photo that we sent out, with our 6-year-old English Bulldog, Joan.

I’m not wearing that.

Merry Christmas from your friendly, neighborhood mall goths. 2005

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.

This was the picture that my family sent out as our family Christmas card back in ’91.

We took the kids to take pictures with Santa. Needless to say, we were shocked as we scrolled through the photos and saw our daughter’s middle finger up with her head turned and smiling.

The infamous Christmas photoshoot 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.

This is a picture of me and my dad at Christmas time. Dad was smoking a cigarette and reading.

I tried to get some Christmas card photos with my boys this year. My 5-year-old was NOT having it and refused to cooperate (look under the sign). But this one took the cake for me since the baby is puking as well.

Within these photos lie the candid quirks—the 'merry misfits' captured in these snapshots, the 'festive oddity' that paints an unintentionally humorous picture of family gatherings, and the 'holiday quirkiness' that defines the peculiar charm of Christmas snapshots. It's an embrace of the unintentional hilarity that arises when families gather for the holiday season. Exploring the internet reveals ongoing threads on 'awkward holiday photos' and 'quirky Christmas memories,' where users share and laugh at the delightful oddities of festive family moments.


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