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Bender said that holidays really do mean more awkward shots. "Families are more likely to get together and take photos," he told Bored Panda. "Plus, a lot of families have holiday traditions like dressing up in matching outfits which always leads to [even more] awkwardness."

But Bender said there are other occasions that produce these pictures too. Like birthdays. Someone will undoubtedly capture the kids in their most (you guessed it) awkward stages of life. And weddings. "You are bringing together not just one awkward family but two and generally, people are intoxicated and I don't think I have to explain how that can get weird," he pointed out. Lastly, he mentioned hospital delivery photos. The mothers never seem as enthusiastic about taking pictures as the dads!

#2

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

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

Final score:

386points

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Raine Soo 3 years ago

All I can think of is an old horror movie called "Hounds of Hell".

63points

"The pandemic has brought all families closer together. We're spending more time with each other and so we're also taking more photos. Also, we truly can't get away from our family when we're in quarantine so that ensures lots of awkward moments. As far as Christmas, we like to say it's the most awkward time of the year and the gift that keeps on giving."

#3

The Only Baby Picture I Have. Why?

Final score:

362points

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Titas Burinskas 3 years ago

The only baby picture you need

228points

#4

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

Final score:

328points

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Caged Beer 3 years ago

You sure got the look.

61points

#5

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

Final score:

318points

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Berry Budgie 3 years ago (edited)

DANG THE ONE YEAR THE FAMILY DOES NOTHING WRONG

130points

#6

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

Final score:

315points

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Berry Budgie 3 years ago

One kid smiling

82points

#7

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

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

Final score:

304points

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Melanie Gallegos 3 years ago

This may be the most awkward photo winner! Lol

92points

#8

This Was The Picture That My Family Sent Out As Our Family Christmas Card Back In '91

Final score:

296points

POST

Hans 3 years ago

Disturbing on many levels. Yet hillarious.

130points

awkwardfamilyphotos Report

#9

This Is The Photo My Grandmother Sent Out As Her X-Mas Card In The Early 70s

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

Final score:

286points

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Scratch 3 years ago

Gran was Photoshopping before it was a thing.

122points

#10

Merry Christmas From Your Friendly, Neighborhood Mall Goths, 2005

Final score:

274points

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Andraya Begley 3 years ago

Santa is being a good sport!

110points

#11

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

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

Final score:

267points

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tuzdayschild 3 years ago

Ralphie's bunny outfit doesn't seem so bad now.

104points

#12

My Dad On Christmas Morning

Final score:

254points

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Raine Soo 3 years ago

Your dad reminds me of a younger Jack Nicholson.

198points

#13

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

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

Final score:

252points

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Berry Budgie 3 years ago

HAH THE CAPTION

101points

#14

Christmas Was Scary In Yugoslavia

Final score:

242points

POST

tuzdayschild 3 years ago (edited)

Soooooo many nopes

117points

#15

My Dad Built This To Protect The Tree From The Cat

Final score:

237points

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Gary 3 years ago

I'm sorry but Christmas is now in quarantine.

146points

#16

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

Final score:

236points

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Berry Budgie 3 years ago

Is that why santa is gone?

68points

#17

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 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

Final score:

232points

POST

Jitka Svobodová 3 years ago

Get up bro! The reindeer is coming! IT'S COMING!!

63points

#18

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

Final score:

231points

POST

Who? Me? 3 years ago

The holly jolly spirit ❄❄

37points

#19

Mom, There’s A Reason There Wasn’t A Line To See This Santa…

Final score:

227points

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Vorknkx 3 years ago

"That weird family had left out a glass of milk and some really strange-tasting brownies..."

14points

#20

The Moment My Mom Realized I Was Going To Be A Handful

Final score:

221points

POST

Who? Me? 3 years ago

This could be a movie poster

129points

#21

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

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

Final score:

219points

POST

Gary 3 years ago

That would actually be a pretty good Christmas card, I would love to get one like that.

80points

#22

This Is The 2006 Christmas Card Photo That We Sent Out, With Our 6-Year-Old English Bulldog, Joan

Final score:

217points

POST

glowworm2 3 years ago

Humpy holidays!

13points

#23

This Is A Picture Of Me And My Dad At Christmas Time. Dad Was Smoking A Cigarette And Reading

Final score:

206points

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Jitka Svobodová 3 years ago

Well he bought it for the articles!

113points

#24

This Is A Picture Of My Dad And Uncles Sitting With Santa. My Uncle Tex Is The Youngest Who Was Clearly A Bit Nervous

Final score:

204points

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Petra Christovová 3 years ago

Uncle Tex must be really happy that this photo made it to the internet :/

90points

#25

The Year My Father Got My Mother A Hoover For Christmas, 1984

Final score:

204points

POST

StormWolf 3 years ago

The appropriate reaction to your romantic partner gifting you a household appliance for XMAS lol. And yet I'm not opposed to receiving useful gifts (I'm now at an age where the thought of receiving a snazzy new Hoover genuinely excites me!) but maybe not at christmas...

127points

#26

Every Romanian Child's Christmas Summed Up In One Picture

Final score:

193points

POST

tuzdayschild 3 years ago

I can't think of many things on earth scarier than this Santa.

93points

#27

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

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

Final score:

191points

POST

Caged Beer 3 years ago

That baby on the right has a very knowing look.

43points

#28

Just A Good Old Holiday Pic With An Innocent Little 4-Year-Old, A Creepy Santa And A Scantily Dressed Miss Piggy! Even More Disturbing, Why Does The Costume Even Have Those Body Parts Sewn On?!

Final score:

185points

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Caged Beer 3 years ago

Words fail!

76points

#29

This Is A Picture Of Me Around Age 3 Or 4, Meeting St. Nicolas Himself In Poland. This Would Explain My Fear Of Clowns

Final score:

179points

POST

Berry Budgie 3 years ago

Looks like a white reaper here to take you to hell

91points

#30

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

Final score:

169points

POST

Berry Budgie 3 years ago

Tears of joy...

63points

#31

My Boyfriend When He Was 3. The Ussr Was A Strange Time

Final score:

165points

POST

Andrew Gibb 3 years ago

there is a Russian Winnie the Pooh as well called Vinni Pukh vinni_pukh...d6bb08.jpg

49points

#32

Most Awkward Pajama Pics!

Final score:

163points

POST

Berry Budgie 3 years ago

Le man boobs

77points

#33

Our Awkward Family Swim Team Christmas Photo

Final score:

155points

POST

Loki’s Lil Butter Knife 3 years ago

I just noticed that they decorated the tree with all of their racing ribbons.

70points

#34

Me And My Parents, December 1992

Final score:

149points

POST

Dan Buczynski 3 years ago

So much is right in this pic

37points

#35

Christmas In Frankfurt, Germany, 1998. My Grandma Knitted Sweaters For My Granddad, Cousin, Brother And Me

Final score:

145points

POST

Jitka Svobodová 3 years ago

She didn't want to waste yarn on dad thou

80points

#36

The Holidays Are The Cringiest Time Of The Year!

Final score:

135points

POST

Who? Me? 3 years ago

Santa melted

59points

#37

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 Deliver Gifts To Kids On Epiphany Eve

Final score:

132points

POST

Andrew Gibb 3 years ago

I've had an epiphany- get the hell out of there!

78points

#38

This Photo Is From Azerbaijan Which Is Old Ussr Country. I Was 6 Years Old In This Last Day Of 1999. It Is Nice To See How East And West Meld In One Photograph

Final score:

131points

POST

Call Me Mars 3 years ago

I live in Azerbaijan as an expat currently!

26points

#39

Christmas Sometime In The Early/Mid 90s And This Is Me And My Two Sisters. My Neighbor Worked For Marlboro Cigarettes And My Mother Decided That Since Their Company Sweatshirts Were Red, We Should All Wear Them For Our Christmas Pictures

Christmas Sometime In The Early/Mid 90s And This Is Me And My Two Sisters. My Neighbor Worked For Marlboro Cigarettes And My Mother Decided That Since Their Company Sweatshirts Were Red, We Should All Wear Them For Our Christmas Pictures

Final score:

131points

POST

ƒιѕн 3 years ago

Yes, Christmas promoting lung cancer.

58points

#40

So Many Amazing Things About This Picture. I Am The Beauty With The Middle Part Bangs Accompanied By My Life Size Barbie. My Mom Is Clearly Feeling What Every Mother On Christmas Feels While My Dad Is 90’s Fabulous

So Many Amazing Things About This Picture. I Am The Beauty With The Middle Part Bangs Accompanied By My Life Size Barbie. My Mom Is Clearly Feeling What Every Mother On Christmas Feels While My Dad Is 90’s Fabulous

Final score:

128points

POST

Berry Budgie 3 years ago

Mum knows she is cleaning ALL the wrapping paper😂

44points

#41

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

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

Final score:

124points

POST

rabbitsrabbit 3 years ago

who knew they invented 5 minute crafts clothing hack edn?

43points

#42

My Husband's Coworker When She Was A Kid

Final score:

120points

POST

Caged Beer 3 years ago

Step away from the child!

96points

#43

Christmas Morning, And Everybody Except Young Tim (Middle) Gets A New Bike. We As Parents Should Have Anticipated The Reaction

Final score:

120points

POST

Berry Budgie 3 years ago

Thats mean tho...

80points

#44

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

Final score:

114points

POST

E Menendez 3 years ago

This looks like a pharmacy... I some how do not feel this was a legit Santa but some dude in Walgreens or CVS trying to get kids to sit on his lap...

45points

#45

I Refused To Sit On Its Lap

Final score:

114points

POST

Who? Me? 3 years ago

Has Santa got flu ?

38points

#46

Me And Another Small Town Goth Going Dancing At A Winter Formal

Final score:

114points

POST

Melanie Gallegos 3 years ago

He looks soo creepy! And she looks super tiny!

58points

#47

My Brother And Me, Circa 1977, With The Credit Union Santa And His Creepy Bear Sidekick

Final score:

107points

POST

Artoonist Corine 3 years ago

I had a coat like that!

19points

#48

This Picture Was Taken In About 1952. The Boy Sitting On The Lap Of ‘Santa’ Is My Husband’s Cousin, Teddy. ‘Santa’ Is ‘Uncle Bob’ Who Apparently Didn’t Notice That His Mask Was Melting Off. My Husband Thankfully Doesn’t Remember Any Of This. No Word If Little Teddy Ever Recovered From The Trauma

This Picture Was Taken In About 1952. The Boy Sitting On The Lap Of ‘Santa’ Is My Husband’s Cousin, Teddy. ‘Santa’ Is ‘Uncle Bob’ Who Apparently Didn’t Notice That His Mask Was Melting Off. My Husband Thankfully Doesn’t Remember Any Of This. No Word If Little Teddy Ever Recovered From The Trauma

Final score:

107points

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PandaLuvs 1 year ago

'Little Teddy' looks high.

1point

#49

Christmas 1998. I'm The One Crying

Final score:

99points

POST

John E. Bedder 3 years ago

The Santa of the Opera.

106points

#50

My Mom Took My Brother, Sister And I To The Mall To Get A “Nice” Santa Photo Taken. When She Picked Up The Photo, She Was Outraged

Final score:

90points

POST

chi-wei shen 3 years ago

A bit awkward but no reason to be outraged.

53points