When I was a little kid, I kinda hated getting my photo taken. Going to the seaside was about the sea and not keeping my hair nice for twenty minutes while my father was getting a hold of his new camera. Christmas was also a drag. I mean, exchanging presents and sitting at the table was wholesome, but organizing everyone in front of the damn tree so nobody would fall out of frame — not so much.
However, family photos aren’t just for the people in them but for future generations as well. Someday, my children, nieces, and nephews will look at them and realize that my crooked smile doesn’t mean I hate them. They’ll realize I’ve had it since forever. And hopefully, it’ll make it easier for them to get along with my grumpy old butt. They’re about creating memories, documenting growth, and revealing character.
Awkward Family Photos is an online celebration of these things. It’s a place that invites people to submit all the funny, cringy, and of course, awkward moments their family has caught on film, proving that we all know how to make a fool of ourselves, and our descendants will certainly get to enjoy that.
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#1
“My adorable son was a wee bit chubby as a baby.”
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#2
“My mom has this picture hanging on her wall in her house for everyone to see. She sends it to me every Mother’s Day. This is me when my kids were little. Apparently my kids needed me and so did the dog, while I’m on the toilet.”
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#3
“My siblings and I were forced into a ‘pet look alike’ competition. It still haunts us.”
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#4
“Me picking mushrooms in Belarus in 1987, one year after the Chernobyl meltdown in neighboring Ukraine.”
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#5
“My mother and grandmother demonstrating safety standards in the 1960s.”
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#6
“My cousin. 1970s. No words.”
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#7
“It was my kid’s birthday party and we were told we were getting a pirate slide.”
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#8
“Halloween 1994, when my parents told us they were a sock and a sock box, and asked us to put on our white pajamas, because we were dryer lint.”
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#9
“I was baptised when I was about 10 and yes, those are my legs.”
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#10
“My Mom took me to a Glamour Shots in the mall when I was 11 years old. I walked out as a middle aged woman who wants to speak to the manager. This is framed in my parents living room.”
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#11
“My dad teaching math in Southern California, late 70’s/early 80’s.”
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#12
“We had the worst wedding photographer in the world. I think this says it all.”
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#13
“When your Grandma looks like Taylor Swift and your Grandpa looks like Hugh Hefner’s Brother.”
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#14
“My swag peaked in 1987.”
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#15
“This is a photo of my mom, my brother, myself, and my soon to be born younger brother. I’m awkwardly in the hockey equipment on the bottom left. A family friend talked mom into having us all pose for this photo. It went on to win some sort of award in a Newport, RI photo show. It also hung in our house while I was growing up, which made for some awkward moments when friends came over.”
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#16
“This was the only bench around to rest after a long hike, so we sat and took five….”
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#17
“I have yet to receive an explanation as to how or why I am sitting in the toilet.”
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#18
“My Mom’s bed hung from chains, and she had a mini bar for a headboard. 1972.”
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#19
“This photo of my family was taken as a Christmas Picture in late 1989, after my younger sister (the “pearl”) was born.”
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#20
“Grandma fell asleep. Then the tide came in.”
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#21
“Grandma wanted a photo with her Thanksgiving table settings. Nobody thought to check the mirror.”
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#22
“Just thought I’d share this old picture I found of me and my dad. Hopefully you guys enjoy it as much as I did.”
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#23
“This was me and my brother at our aunt’s wedding. His pants were too big for him, but we thought he’d be okay. Of course, his pants came down at the altar.”
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#24
“It was 4th grade Space Week, I was really into it, and the class had the opportunity to get extra credit if we wore something that had to do with space. Just wearing a space camp shirt would not suffice so yes, that’s an aluminum foil space suit complete with grey boots.”
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#25
“Congratulations to our Weirdest Family Photo winner whose mom cropped out his prom date (at least most of her) to make his new wife feel more comfortable and congrats to all of our strange runner-ups!”
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#26
“My friend had a surfing chicken when he was younger.”
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#27
My grandfather sent me this photo, which he took in celebration of his eightieth birthday.”
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#28
“This picture was taken at my daughter’s preschool. I think the photographer thought having her hold a flower would make for a really cute and innocent picture.”
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#29
“This old picture of my great-grandmother, far left, makes it look like the cameraman just stumbled into a secret meeting of the grandmas.”
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#30
“I found my spirit animal at a very young age.”
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#31
“One year my mom made my brother and I outfits from the drapes that came with our beautiful couch.”
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#32
“After my sister broke up with her boyfriend, my Dad spent hours learning how to photoshop so he could seamlessly remove him from our photos. One of my favourite pictures to this day.”
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#33
“My Great-Grandmother, born in 1899. Never met her, but definitely a legend.”
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#34
“Not sure what grandma and her friend are up to.”
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#35
“Me when I was 3, in a porcupine cosplay, I guess. So fun to be the youngest sibling.”
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#36
“This is me back in ’93 at the Brantford Skating Carnival. The show was beauty and the beast, and I was a piece of cutlery (a spoon). I had to wear a horrible white unitard, and everyone said I looked like a toilet seat. The worst part is when we were on the ice, it glowed in the dark!”
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#37
“This is my brother’s senior photo. A “hot” mess.”
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#38
“This is my friend’s husband inside a pumpkin bounce house. Nothing better than a family outing where you see a live breech birth.”
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#39
“My grandpa grew this massive carrot in his garden, my sister ate the whole thing and her skin turned orange.”
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#40
“My mom and dad in DC in the late 80s.”
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#41
“My friend’s three-year-old son in preschool today.”
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#42
“Our social distance Easter photos turned out terrifying.”
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#43
“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.”
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#44
“I took my 2002 Senior Year with my bird, Jeff. It made the yearbook. 10 years later, I caught him reflecting on our long history. Sentimentality in its truest form.”
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#45
“My mom was so excited when it was time to renew her driver license and get a new picture taken. She made herself a DMV appointment, had her hair done the day before, and gave herself extra time to get herself picture ready for her new driver’s license picture. This was the result.”
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#46
“My great-grandmother worked for a photography studio in the 80’s. She was watching us one day and decided to surprise my mother with professional photos of the three of us. This gem was one of the pictures. I love how my sisters look so cute in the corner of the photo while I am in a food coma floating in the sky.”
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#47
“This is me and my dad 1977 Coney Island. He would be vilified and in jail today for this.”
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#48
“My friend managed to make this bubble.”
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#49
“This was my mom’s friend on vacation, she just learned how to take selfies and work Photoshop. And so, this gem was born.”
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#50
“Meet Uncle Jack, the goth uncle.”
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#51
“My friend’s baby pictures look like Mrs. Doubtfire.”
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#52
“Fight that broke out at my great-uncle’s wedding, 1968.”
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#53
“This is me and my sister in 1972 posing with the doll we found at our grandparents house. Seems granddad had a “thing.”
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#54
“My daughter in Bonbon Land in Denmark, 2004.”
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#55
“My dad in a cow-milking contest before a baseball game, 1977.”
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#56
“It was the worst vacation we ever took.”
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#57
“I thought I struck gold, a doll to play with that was bigger than me! So I dressed her up and rode around with her on my bike.”
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#58
“Me and my Dad. It looks like I was raised by Ron Jeremy.”
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#59
“This is a photo of my parents and all of our heads: four daughters and their respective families. My Dad loves photography, and recently purchased a green screen so that our family photos could miraculously be in any lovely location in the world. This one, however, highlights the fact that he might want to improve his cutting and pasting skills.”
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#60
“On a family outing to the museum, we got more culture than we bargained for.”
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#61
“During a cousins photo shoot, my brother fell off the stool mid-temper tantrum and the photographer managed to catch all of my cousins’ reactions.”
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#62
“There’s a reason why my sisters were accepted into private school and I wasn’t.”
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#63
“The year is probably 1999 and this is my turtle Halloween costume from 3rd grade. My mom made it for me and I won 3rd prize.”
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#64
“I was born in 1981, but turned 55 in 1992.”
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#65
“My parents wedding day. 1980s.”
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#66
“In the UK we had a TV ‘personality’ called Mr Blobby. My father rented a Blobby costume for my school fair and after trying it on for the first time tripped and fell down the stairs, splitting the suit on the bottom in doing so. Yes that’s me at the bottom of the stairs blissfully unaware of what was hurtling toward me.”
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#67
“My grandma is a little nutty.”
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#68
“My great-aunt uses her old television as a stand for her new one.”
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#69
“If your mum wasn’t making herself into a ramp for your new BMX, did she even love you? 1980’s.”
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#70
“My parents keep this framed on the wall. It’s a poem written and illustrated by my brother in second grade.”
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#71
“My friends Grandma’s house. She put a magazine cut out of Leonardo DiCaprio over her late (not so nice) husband’s face. The 80+ year old’s version of photoshop.”
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#72
“This is a photo of my daughter and her father riding the Tennessee Tornado roller coaster at Dollywood. When we saw the photo at the sales kiosk, we laughed so hard we just HAD to buy it!”
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#73
“Grandma made these wonderful crochet vests for each of my husband’s siblings. He looks strangely happy about it. (far right).”
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#74
“We went to the beach to find shark teeth, so when my daughter yelled ‘I found teeth!’ This was the last thing I was expecting.”
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#75
“My daughter looks like a mom that regrets all her life decisions.”
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#76
“My daughter was born during lockdown and we couldn’t hire a photographer. I tried.”
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#77
“That moment you realize you’re not the only child anymore.”
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#78
“My mom with her brothers and sisters in the 1980s.”
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#79
“Got my 10-year-old daughter dressed up for a nice New Year’s Eve dinner and tried taking a pretty picture of her. I got a haunting photo that looks like she is missing her evil twin.”
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#80
“My German grandparents on a trip to Disneyland in California in 1995… my Grandma apparently didn’t enjoy the ride while Grandpa had the time of his life.”
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#81
“We were taking our daughter’s newborn photos and she would not sit still. The photographer had me lay under a blanket so our baby would feel like I was holding her. I was told not to move. Lasted 90 minutes.”
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#82
“My grandpa posing with his ‘tomato plant.’”
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#83
“My mom said this was one of my favorite things to do as a child.”
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#84
“An uncle gifted my sisters and I dolls made to look like us (they even had matching moles and freckles). My mom felt it was necessary to have professional photos taken with them. Thanks.”
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#85
“My date for prom (now my husband of 28 years), picked me up at my house and took a few pictures. Then we stopped by his parents house and his dad was mowing the grass. His mom made him get off the mower and get a quick picture with us.”
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#86
“Sometimes we lose my grandma.”
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#87
“Bring a toddler to a wedding, they said. It will be cute, they said.”
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#88
“I bought my grandad a HUGE tub of his favourite chocolates and he emailed me this photo to tell me that he had finally finished them.”
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#89
“When I babysit my niece she makes me play Operation. Her favorite part is when she dies and we have a funeral for her.”
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#90
“There was a moth in our kitchen.”
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#91
“This is my brother and I at Christmas, 1965. I was only 6 months old and my brother obviously thought I was annoying, if not repulsive.”
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#92
“My mom was Amish in the 90s. Apparently when this picture was taken she was in trouble with the church for breaking off three engagements.”
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#93
“This magnificent awkward moment was my high school graduation photo from 1997. I remember thinking to myself ‘don’t fall, don’t fall, don’t fall!’ while precariously balanced on what I can only assume were old books under a wrinkled drop cloth. When the photos were sent to me I was too mortified to give them to anyone; in fact I still have the full sheets of them in a bin in my basement. I’m actually 17 in this photo, and I just recently turned 40. Not everyone gets to experience their 40’s twice in life. I just happened to do it the first time when I was in my teens.”
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#94
“On vacation in Mexico, I was kissy-facing with my daughter. Not sure if this guy was in the wrong place at the wrong time, or the right place at the right time.”
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#95
“My friend’s childhood glamour shot.”
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#96
“My dad and I getting ready for a road trip in the summer of ’86.”
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#97
“This is a photo my mom captured of my then 2 year old daughter.”
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#98
“Holding my Mom’s cigarette while she zips my coat.”
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#99
“As a kid, my parents never understood why I never wanted to spend the night at my Aunt’s house.”
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#100
“My family loves Halloween. Here we are in 1982 with my dad as…who even knows? My mom as an alien? My sister as ET, and other sister as Pac Man. I’m the baby and I think dressed as a duck?”
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#101
“My parents just texted this to me (they’re babysitting). It’s pouring rain and my dad is teaching my girls ‘how to clean gutters.’ They’re thrilled.”
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#102
“Reason #82 why dads shouldn’t be left alone with their kids.”
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#103
“‘I didn’t ask for this,’ said our very stubborn 2.5 year old. He had the same expression in every photo from the session.”
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#104
“My wife was the flower girl for her cousin’s wedding and decided to slide down the railing while the bird seed was flying after the happy couple was married. This was the result.”
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#105
“My great-grandma in the 80’s.”
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#106
“This is how my 2.5-year-old niece insists on holding her baby brother.”
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#107
“This is how my girlfriend posted our photo op with Jason Momoa.”
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#108
“Another win for the panoramic camera function.”
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#109
“This is my parents leaving my grandmothers house after staying there for a month after I was born! My mother didn’t believe she actually could take care of me alone, at 28 years old! That’s my grandmom locking the door in the background! Thankfully they turned out to be good parents!”
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#110
“My niece decided that her cats should sleep in bunk beds.”
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#111
“At my best friend’s wedding, we were extremely determined to catch the bouquet.”
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#112
“This was taken Easter morning in 1986. That’s me and my little sister (14 years younger than me) I had come home from college for the weekend and must have been out the night before. I obviously wasn’t too happy about having to wake up early for Easter festivities. I think when my Mom took this picture, she was just happy to have her son home from college to help celebrate the holiday. The contrast of my little sister all frou frou in her new Sunday dress and me barely dressed, sporting cheesy glasses and a sleazy mustache is just too much.”
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#113
“This is love. My dad is driving and my mom is squirting ranch on each carrot he holds out.”
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#114
“My father-in-law babysitting my 2 year-old daughter Lillian. I’m just thankful they BOTH fell asleep at the same time :)”
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#115
“My grandmother and great grandmother around 1992 or 93. According to my grandma, ‘We went to one of those photo places in the Palm Desert mall and they duded us up like floozies. We howled when we saw these pictures.”
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#116
“My dad took me to the mall to get Glamour Shots done for my tenth birthday. I was so excited, this was everything to me. I turned out to look like a 40-something real estate agent, and a possible Delta Burke twin. Designing Women, here I come! LOL!”
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#117
“My daughter was supposed to be a flower girl in her aunt’s wedding but napping is life. (She was safely strapped in).”
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#118
“The baby’s foot looked like something much, much different.”
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#119
“My husband on the couch of a house we rented in St John.”
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#120
“My cat messed up a single part of my window shades. Never realized why until just now.”
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#121
“My mother keeping it classy in these uncertain times.”
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#122
“This is a portrait of me and my mom taken at the local Woolworth’s in the late 70’s. My mom thought it would be cute to take photos in our tube tops. I posted this pic on FB as it’s always been one of my favorites; I thought it was so sweet. Two weeks later, a friend saw it on FB and suggested that it could be a contender for your site. I HAD NEVER THOUGHT OF THE PHOTO IN THAT LIGHT, but now that I see what others see, I can’t stop laughing.”
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#123
“When I was in 6th grade, my two older sisters were popular and had big hair, and I was an awkward kid so I thought I’d be cool for a day. I went to town on the Aquanet hairspray. I used almost half a can to get this Big Bang as tall as I could. The photographer literally had to take a step back to fit my hair in the school photo and i really don’t know how he kept a straight face. I shared this on Instagram once and couldn’t even fit it in the crop.”
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#124
“We had just had our daughter two days ago. Nothing says ‘omg what have we done?’ as much as this picture.”
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#125
“This is the way my mother found my sister sleeping. In her pajamas she has a puppet, a stuffed monkey, a stuffed seal, two blankets, and a watch.”
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#126
“As a child, I would dress up as a clown whenever there was a reason to celebrate – in this case the birth of my younger brother.”
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#127
“My boys came into the world peeing on each other.”
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#128
“Our trip to the petting zoo did not go as planned.”
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#129
“Today I welcomed my first child into the world. Here’s a photo of me waking up after passing out in the OR.”
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#130
“My daughter’s reaction when holding her new baby sister. Much heavier than the dolls she practiced on.”
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#131
“I was born with a lazy eye. Instead of wearing an eye patch, my parents thought blue masking tape would be less noticeable.”
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#132
“Our family friend’s dog also has his favorite place to binge watch his favorite show.”
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#133
“Ironically her toy turtle was named ‘Turdy,’ a few days later her destiny was fulfilled.”
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#134
“My son was a little upset when he outgrew the Radio Flyer.”
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#135
“The only way to really do Easter – circa 1950.”
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#136
“Friend showed me a picture of her parents in the 80’s…and it is truly PURE 80’s.”
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#137
“My dad wanted to take a nice picture with a waterfall in Yosemite.”
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#138
“My brother at 4 weeks. He reminds me of an old celebrity, just haven’t figured it out yet. Any ideas…?”
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#139
“Our AirBnB had a translucent bathroom door. I’m used to my impatient toddler stalking me through the bathroom door, but this took it to a much creepier level.”
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#140
“This is Mother’s Day, 1994. My grandmother asked to try out my new pogo stick, and my mom was there to capture the result.”
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#141
“Early 90s there was a train derailment onto a gas line near our house. Grandpa thought that was a nice photo op and drove my little brother to the explosion.”
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#142
“This was the gem of my high school senior picture portfolio. At the time, the effect was cutting edge. Now I like to tell my kids that I had to skate really fast to look that dumb.”
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#143
“My buddy’s childhood picture would make Joe Dirt jealous.”
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#144
“My wife’s face on our wedding day compared to when she met Rob Lowe.”
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#145
“Bob Ross with two baby squirrels.”
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#146
“My father, killing it on the 4th of July, 1990.”
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#147
“Her husband went to the pregnancy room with her to cheer her up.”
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#148
“My dog showing my girlfriend that I’m his.”
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#149
“This was my Christening, June 1971. I’m the baby obviously, my Godmother is holding me, my parents are next to her. Their hideous outfits aren’t the “awkward” part of this photo. In the background, my grandmother is pulling my sister’s hair while my brother is recovering from a smack! All of this right on the front steps of a church.”
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#150
Yes this was me. Yes my parents actually paid a photographer to take these staged photos. And yes, that last photo is my look of complete disbelief and exhaustion when I found out that I was related to these “adults.”
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#151
“One of our goats and I are both pregnant with twins and due the same week. I made her dress up and take maternity photos with me.”
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#152
“All week long at this Jamaican resort, we kept running into this man. On the last day of our trip, we had to pose for this photo.”
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#153
“A local farm where I live had trouble with their flock all wanting to sleep in the same house. The other night they found their dog had joined in.”
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#154
“My awesome grandma and her even more awesome hair.”
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#155
“I’m about 2 or 3 in this photo. We were at a family friend’s wedding. Apparently my mom was having fun dancing and not paying attention to me. I bit her in the butt, legend has it that I drew blood.”
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#156
“This was my first birthday. I picked up all the liquor glasses on the table. Passed out, mom called medic, he made me throw up and they put me on the throne. End of story.”
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#157
“My sister took her daughters to go apple picking in the fall in the hopes of getting a good picture together. The kids were not cooperating and my sister’s face in this picture perfectly encapsulates how she felt about it.”
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#158
“A friend bought a new house in 2017. When a cable technician went into the crawlspace they found this shrine to Nicholas Cage complete with candles, goblet, kneeling rug and lockbox of movie paraphernalia.”
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#159
“This is my husband and I on the morning of our wedding 20 years ago. We were having studio pictures taken and the local photographer proudly rolled out this faux bay window and told my soon-to-be-husband to ‘peek in from outside.’”
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#160
“My sister has four boys. She couldn’t find the youngest. And here he was!”
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#161
“I’m in front, brother in back, mom on right. In a hot tub in a garage in Vail, CO ~1977 after a day of skiing. Brother with very unfortunate head gear (how come kids don’t have to wear that anymore?). Brother and I were in inner tubes, for some reason. I’m pretty sure my mom DOES have a swimsuit on.”
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