The 20 Most Awkward Family Photos We Have Ever Seen

  • 1

    Trading places

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    "My husband couldn't make it to the family portrait photo shoot. Rather than cancel, I brought a "replacement". This is what went in all our Christmas cards. My husband's family was not amused and he wouldn't talk to me for days."

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  • 2

    We love this family!

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    "My hubby is a teacher. I'm a stay-at-home Mom. We have 5 kiddos, 4 of them adopted through foster care. A long time ago, I heard our pastor point out that when it comes to kids, rules without relationship = rebellion. From that day forward, I made a promise to myself to always make relationship with our kids a priority. And that means having fun with them and having a sense of humor. We want to teach our kids that being able to laugh at yourself (not in a bad, degrading way, but in a good way) is a wonderful attribute. So, we always do crazy photos for our Christmas cards. This year, we decided to make an awkward family photo."

  • 3

    Christmas Casual

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    Somebody wasn't cc'd.

  • 4

    Dress porn

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    "My grandmother, bless her heart, made this dress for me by hand. However, she never noticed the fabric she was sewing was covered with pictures of a couple making out. She then rolled my hair and sent me to school…on PICTURE day… I still love you MawMaw."

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  • 5

    Recreation: what about grandma?

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  • 6

    Barbie arm

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    "We took this picture at a friend's wedding. It wasn't until after I posted it and people started making comments about my husband's "Barbie Arm" did we notice how his arm had 'shrunk'…"

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  • 7

    Double vision

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    "The year was 1976. My mom had just come home with that fabulous perm, and, apparently, I asked to have the same done to my hair. I was three or four at the time, so I'll have to take her word on that. I do, however remember the traumatic experience of having that fro cut off several days after this picture was taken, because I played in a sandbox too emphatically and my mother couldn't comb through the tangled, sandy mess! This picture will always make me smile (while shaking my head). It shows just how tiny our immediate family was – just me and my mom, with dad behind the camera at his studio. It's goofy, sure, but back then, it was just 'us'.

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  • 8

    Reindeer games

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    "I had this same type of photo taken of all three of my kids but when I pulled out the reindeer antlers for my last child, the photographer that I had used for 15 years said 'Oh please, No. I'm going to have to call Social Services.'"

  • 9

    Falling slowly

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    "My daughter and I had been holding hands and she was leaning away from me and our photographer caught the perfect moment! So the rest of us are looking fabulous while my 2 year old is crashing into the pavement!"

  • 10

    Vacation Bunch

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    "This was taken just before we were attached to a steel cable and hurled through the Thai jungle (like a flying fox – the tour was called "Flight of the Gibbons.") As you can see, my husband looks like he was quite excited about the tour."

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  • 11

    The rub

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    "This is my husband when he was 6 or 7. His grandma sent him to school on PICTURE DAY in this shirt. You can't see the bottom, but the shirt actually says "Rub it easy, make it hard." No joke. His grandma obviously was clueless. Needless to say, he didn't wear it to school again."

  • 12


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    "This is hanging in my cousin's house. They hired a new family photographer that year and thought this was a great idea."

  • 13

    Just the facts

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    "This is a photo of my sister (the murderer), my brother (the reporter), and my Dad (the victim). The way I've heard the story told, as I was still a few years from being born, they lived next to a reporter for the local news channel and one day, my dad decided it would be funny to stage this picture…complete with "blood stains" on his back. The back of the picture actually says, "Just the Facts, Ma'am, 8/01/75."

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  • 14

    Little Miss Sunshine revisited

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    "My mom loved to get professional photos taken of my siblings and me when we were kids. I hated it. I learned fairly quickly that if I complained or was fussy they would just keep going and ask me to be still or quiet. However, if I behaved perfectly and just made awful facial expressions the photos would end. This little gem is a product of my silent temper tantrums."
    Oh, and btw, this is Meg now.

  • 15
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  • 16

    The gift of innosence

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    "My 8 year old went dumpster diving in our neighborhood. He was so proud. He brought this home for me, because it has a heart on it."

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  • 17

    Renaissance Regrets

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    "I lived in Luxembourg as a kid so my family did a lot of traveling in the five years we lived there. I was going through some old family photos this weekend and found the ones from our trip to Italy. In looking through the pictures, it was obvious that my siblings and I were not happy campers on this trip as we all refused to smile in every picture. However, this picture and the look on my face says it all! I'm sure my Dad thought it was hilarious to have his eight-year-old daughter pose in front of a fat naked man sitting on a turtle.
    The statue is 'The Fountain of Bacchus', sculpted in 1560 by Valerio Cioli. He used Duke Cosimo I's court dwarf as the model for Bacchus. If you want to see the statue today, or take your own picture with it, it's at the Boboli Gardens in Florence, Italy."

  • 18

    Direct hit

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    "This family portrait was taken during a beach photo session. Yes, that is a frisbee flying towards my husband's face. Fortunately, nobody was seriously injured in the process, and we DID end up using this picture on our Christmas card that year. It just pretty much sums up our family in a way no words can."

  • 19

    The Christmas Goose

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    He was just pointing out the man who deserves all of the credit.

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  • 20

    Recreating the awkwardness 2

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  • 21

    Bad Santa

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    She wanted second-hand smoke for Christmas.

  • 22

    Ooops, child...

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    "As you can see, I'm obviously the 'oops' child."

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  • 23

    Doll House

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    "This is a picture of my husband and his mother that has been on our shelf for years in our bedroom. My husband just noticed the creepy guy in the window in the back."

  • 24

    Seal it with a kiss

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    "My grandmother trying to steal my dad from his new bride!"

  • 25

    Packing heat

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    "My aunt and uncles family portrait from the early 90's."

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  • 26

    The puke mystery

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    "During family pictures my bouncy 5-year-old was a little sluggish but I was thrilled that he wasn't hyper. When my photographer said "Ummm he just threw up," I thought she meant the baby, so I checked him for spit up, saw none, and said, "No he's good." Then I saw the puddle at my feet. We rushed to the car and as we were driving away the photographer flagged us down to show us the picture she had captured. We laughed so hard we cried.
    That was the only time he threw up that day, and he was totally fine and hour later, so we were puzzled. The next day, as my husband and I kept discussing that he must have eaten something that upset his stomach, he finally came clean. While we had been upstairs getting dressed, he snuck into the kitchen and ate a whole tub of ice cream. Then he cleaned up the mess and thought he got away with it. Apparently, he didn't understand how that much ice cream would make him so sick. He learned the hard way! And it made for a great Christmas card!"

  • 27


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    "This is my Dad prancing around in his cut off jeans. The two older women in the background look generally concerned, and with good reason. Yeah I see where I get my extreme enthusiasm for jorts."

  • 28

    Recreating the awakwardness

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  • 29

    Always on my mine

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    "I came across this pictures of my mom's family today. My Grandmother still thinks this picture is beautiful and doesn't understand why people giggle about the awkwardness."

  • 30

    Smiling not allowed

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    "My mom didn't like regular family portraits, the ones where everyone cleans up and pretends to like each other, because that would not be an accurate portrayal of her kids. This photo is the second in a series of really freaking embarrassing at the time, but funny as hell now, family portraits. Our only obligation, aside from dressing for the theme, was to NOT smile. This was the most important and we would all get passed if we had to wait for another jackass to stop smiling. Sometimes it took forever. But yes, smiling was not allowed. This picture was the 2nd we had done. The first, we dressed in camouflage and toted water pistols in what has been lovingly named Camp Nicaragua. There was also the Lion Tamer, The Beach, and I think the last one was some Little House On The Prairie theme. But please, don't smile.


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