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    Categories: ListiclePARENTS

15+ Awkward Pictures From Family Photo Albums That Had Us Laughing Our Heads Off


Family is the most important part of our lives. Sometimes looking at family photo albums, we experience different kinds of emotions. Important life events, awkward shots, photobombs, and casual moments captured on paper keep the memories alive. And quite often these memories make us laugh out loud.

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Smalljoys gathered 15+ awkward family photos that are too good to be true.

1. Denim paradise family from the early 90’s

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2. “A picture of my friend’s little cousin before and after his first day of kindergarten”

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3. “My parent’s wedding day, 1980s”

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4. “My mom’s kindergarten picture from 1969. My grandma was attending hairdresser courses and loved to practice on her daughters.”

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5. Delta airlines lost this groom’s luggage before the wedding.

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6. And the “Sister of the Year” award goes to…

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7. Probably not the best choice of t-shirts for picture day

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8. “My sister ordered a photo album for her engagement party. The people who made it apparently googled ‘engagement’ and used the first quote that came up.”

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9. “My daughter has a hard time of saying goodbye at Pre-K.”

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10. “My trip to Hawaii, circa 1995”

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11. Those awkward pauses in the middle of a conversation

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12. “The photographer told us to genuinely smile and laugh.”

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13. He never ever smiles. A family portrait from 1993

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14. My mom and her high school crush at prom, 1976

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15. I bet they didn’t expect that when they took this selfie in Berlin.

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16. My mom’s senior portrait, 1988

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17. “Me, my aunt, and my mom, August 1990”

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“So I heard you guys like awkward family photos and pictures of pets… Well, check this out.”

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“Tried to look talented in the background of a family portrait. Failed.”

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“At first, we didn’t get why the photographer stopped taking pictures and fell on the ground laughing. We sent this photo to our relatives.”

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“One day, back in ’81 or so, MawMaw thought it would be a good idea for us to all enjoy a few glasses of her fermented ‘friendship punch’ before heading down to the photo studio.”

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“I don’t remember what was in the box. Some pants, I hope.”

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“Family photo from last fall: we had to physically restrain my little brother, and when he finally got to jump, the photographer caught this gem.”

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“Met Jasmine today. We don’t have kids…”

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“My grandparents’ first time at a Japanese restaurant.”

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“My little brother’s timing was always a little off…”

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“I think this is the only family portrait we have. It’s very important to me!”

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“It was Grandparents’ Day at their church, so they wanted us to haul the kids down for the service. Our son’s friend came along with us. After the service, there was a photo booth for grandparents to get their picture taken with their grandkids. There was also a large container of props available to use. Our daughter absolutely hates getting her picture taken, and the boys are raising hell (in church!) with a dinosaur puppet and small toilet plunger. Priceless.”

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“My mother, the bird whisperer, 1970”

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“This is us with our baby. We are so proud. I guess.”

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“My boss, who has 6 kids, captured every sibling relationship dynamic in one Christmas photo.”

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“My older son went to kindergarten, and the younger one was looking at him through the window. You have to see his face!”

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“Mom got friend-zoned by Dad.”

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“Feeding time!”

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“Dad didn’t have much luck in the arm wrestling circuit, but he has high hopes for his boy.”

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That moment when you realize you’re now the middle child:

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“We tried to get some nice pictures together at Oktoberfest near Portland, OR.”

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“My very favorite picture of my father. He’s the one that set the camera’s timer.”

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“With my daughter and grandchildren at Virginia Beach. Took this photo and noticed the background later!”

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“Dad uncovered this gem from my high school graduation. I wish I could say we staged this…”

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“So my sis wanted a silly family photo…”

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