These Awkward Family Photos Prove Every Clan Has Its Share of Quirky Snapshots

We’ve all been there: that moment during a family gathering when someone enthusiastically shouts, “Let’s take a photo!” What follows is a chaotic scramble of finding the best light, shoving everyone together, and ensuring the tallest are at the back. The final product? Often an awkward masterpiece that perfectly encapsulates family dynamics.

Ah, the beauty of awkward family photos! They are the true treasures hidden amidst our photo albums. They may not make it to the front of the Christmas card, but they definitely capture the genuine essence of our families in all their glorious, unfiltered weirdness.

Remember those themed photo sessions? Like when the whole family decided to dress as wild animals for a jungle-themed shoot, only to have baby Timmy cry his eyes out because he didn’t want to be a monkey. Or the time Grandma thought it’d be cute to have everyone in matching outfits – not the chic, color-coordinated ones, but oddly patterned sweaters that made everyone look like a walking optical illusion.

And who can forget the classic ‘stiff pose’ photos? The ones where everyone looks so formal and unnatural, it’s as if they’re attending a board meeting rather than a joyful family gathering.

It’s not just the outfits or poses that make these photos hilariously memorable. It’s also the unexpected photobombs – be it the family pet making a surprise appearance or the toddler who decides that now is the perfect time to throw a tantrum.

Feeling a chuckle bubbling up from that awkward family memory? Go on, share this post, and spread the joy. Maybe, just maybe, it’ll inspire a family member to pull out that hilarious photo from the last reunion. Ready for a trip down awkward memory lane?

#1 My dog hanging out in the exact spot we tried to keep her out of

#2 My grandma got bit by a pelican on the pier and then began to scold it.

#3 One of our goats and I were both pregnant with twins and due the same week. I made her dress up and take maternity photos with me.

#4 My all-time favorite picture of my sister. She was 6, tired, and had just tried sparkling grape juice. Not a fan.

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

#6 This pretty much sums up my childhood. I’m the blond on the left burying my head in my sister’s lap while she gets in a cheap shot. The youngest is fish-hooking my other sister while my mother looks on and laughs. My father is letting everyone know what his future looks like with four daughters like these.

#8 When it’s your first day of kindergarten and also your first day as head of the PTA.

#9 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.

#10 I asked my grandma if she had some rice that I can put my phone in when it got wet and she pulls this out of a cabinet.

#11 I was just trying to peel my daughter off of me, sit her on the bench, and then I was running to get out of the picture. However, it looks like I have left my children with their sitter and am running away for dear life.

#12 I got a life-sized Barbie when I was 7, and my brother had other ideas.

#13 My poor daughter never heard the end of it from her siblings after her Heartbreaker Tee Shirt turned to Fartbreaker for school pictures.

#14 My dad in high school (1959) vs. me in high school (1986).

#15 My sister looking like she’s gonna tear my head off when I was an infant being held by my dad.

#16 During our ‘perfect’ beach photo shoot, my oldest son jumped on my back, propelling my infant son out of my arms. My infant son was not harmed, just wet and scared but mommy is forever traumatized.

#18 Our grandma used to not only give my sister and me mullets in the 80s, she would then perm them. Matching permed mullets. Need I say more?

#19 My husband as an infant. I prayed our children would not inherit his large cranium.

#20 If your mum wasn’t making herself into a ramp for your new BMX, did she even love you? 1980.

#21 My favorite picture of my parents. Them on their wedding day. 1991.

#22 Our daughter would not cooperate for her photos. She was doing everything but smiling. Here she is getting ready to ‘Hulk’ out.

#24 My daughter was supposed to be a flower girl in her aunt’s wedding but napping is life (and she was safely strapped in).

#25 A photo my mom captured of my then two-year-old daughter.

#26 My great-grandma and her twin sister in Springfield, Missouri. The original inspiration for The Shining, I’m sure.

#28 My husband’s grandfather hung every photo on the wall that he had of his grandchildren. As a test, the family had the grandkids pose by a garbage dumpster and sent it to his grandfather to see what he would do and he still hung it up on the wall. It then became a tradition to send him photos of the family by dumpsters.

#29 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!

#30 It was 1990 so I guess my parents thought they’d dress me up like a New Wave recording artist.

#31 It was my son’s first time on my favorite ride and he was terrified. As for my husband, he just always looks like that.

#32 Vintage 1984 Polaroid of Mr. T pitying me as a baby with my mom.

#33 My grandparents’ Christmas card from 1951 and my favorite annual reminder that font choice matters.

#34 The photographer kept telling my son to ‘smile more!’ and this was his version of smiling ‘more’.

#35 My husband, the blonde, punctured his kidney while wrestling with his brother who is posing on the right. His injury caused him to pee blood and resulted in major surgery. And his little brother couldn’t have been prouder.

#36 My daughter would not stop crying until she got her own cone of shame.

#37 I apologize for my crimes against the ozone layer. High school graduation, 1989.

#38 My mother and grandmother demonstrating safety standards in the 1960s.

#39 This is my sister graduating high school back when you had to wait to get photos developed.

#40 It’s hard to get all 4 brothers to behave for a picture but the oldest sure tried to keep everyone in line.

#41 Came across some old photos of a weird-looking baby at my parents’ house. Found out it’s me at 4 weeks. Thank God they captured my beauty before I grew out of it.

#42 Found at my parents. Not sure if I should laugh or cry?

#43 My great-grandfather’s passport photo from 1978.

#44 My parents just got a hot tub and were very excited about it. Therefore, my grandma hired a professional photographer to take a family photo in the hot tub. For some reason they posed with wine and candles even though the children were not old enough to drink… and sent it out to 150 plus friends as a Christmas card.

#45 Thirteen of grandma’s grandchildren were in the house for a couple of days around Christmas-time. She was pretty exhausted.

#47 Grandma made these wonderful crochet vests for each of my husband’s siblings. He looks strangely happy about it. (Far right).

#48 I received this photo from my dad while he was babysitting my daughter. When she found out grandpa could take out his teeth, he let her wear them.

#49 My 2001 school photo. In order to perfect this aesthetic masterpiece, I put a massive amount of gel in my wet hair, then I bent over and swung my hair around and blow-dried it upside down until the gel hardened completely… I got a little lightheaded each time, but clearly worth it!

#50 Here is my dad with my grandma in 1956 at the snow king chair lift

#52 My husband’s 1st day of school dressed in a cap that looks like a helmet, old school glasses and white socks & sandals while holding his school-issued ‘schultuete’

#53 The time my brother tried to hop over a pole…⁠

#54 My husband hid these from me for years, i was going through stuff to clean out some junk and found them hidden and i almost died laughing

#55 We found my wife’s phone in the toilet. We weren’t sure which of our three kids put it there…until my wife scrolled through her pictures

#56 1993. My siblings and me (the blonde) got the great idea to take a portrait of ourselves for a surprise christmas present for our mom. However, none of us were in the mood for photos on that particular day

#57 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

#58 There’s a reason why my sisters were accepted into private school and i wasn’t

#60 My grandmother and great grandmother in the early 90s

#61 This is what happens when your mother chops off your beautiful, long, thick, crystal gayle-length hair the day before school photos in grade 2

#62 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

#63 When the preacher said ‘kiss the bride,’ my four-year-old decided to put a finger in my butt

#64 My 2 years old daughter wanted to sleep with the skeleton in her room. You choose your battles…

#65 During our annual holiday family photo shoot, we wanted to recreate a cute one we got the prior year when our son was just a baby. It didn’t quite turn out like we hoped it would….

#66 Our kids had experimented with a few different balancing acts and by the time i got my camera figured out, our son had found a new perch

#67 My parents and my little sister on a vacation in croatia. It was a long day and she was quite tired

#68 I was baptised when i was about 10 and yes, those are my legs

#69 It was my 7th birthday and i don’t know why this is happening…

#71 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)

#72 My great-aunt loved these cookies so much, she apparently had my father do a photo shoot with them! This is arguably the best shot

#73 Snapped a nice picture of my dad admiring a gorilla⁠

#74 I was having a great time going through old pictures with my daughter and thought it would be fun to include my mom so i sent her a text of this hysterical family photo that i had no memory of. My mom’s response to my text was more amusing than the picture

#76 Me, my little sister, and my girlfriend meeting santa

#77 Just me, stuck on a fence in a diaper while the neighbor’s kids are getting their kicks, my sister is about to eat dirt, and my brother is creepin’ around in the back

#78 My wife (on the far right) they wanted to dress up as fun clowns and ride around the neighborhood

#79 My ex-husband surprised me after work with a birthday cake

#80 This photo of my 6 month old brother was taken on my second birthday. Apparently my siblings thought it would be hilarious to tie balloons to all of his limbs and my parents were just like, ‘whatever.’ he was the eighth child, so i guess by then nothing mattered

#81 A wedding photo of our very big (and very small) day

#83 Daughter demanded Peppa Pig get the X-ray with her.

#84 The location for the artwork at our local Skate Country is highly questionable…

#85 We were all so delighted to meet our little niece, Erin.

#86 It was the summer of ’68 or ’69, and my mom (holding her cousin) was in Las Vegas with her aunt and uncle to babysit their kids while they went to see Sonny and Cher in concert.

#87 This miraculous photo is of my darling dear mother, in the ’80s, with what is obviously a cutout of the great Thomas Sullivan Magnum.

#88 The whole family went for church directory photos, and the photographer decided to be ‘creative’ with us.

#89 I had a lot of explaining to do when my parents found this on their camera roll. In my defense, he deserved it…

#90 This is a picture of me (in the front) and my family.

#91 In the photo is my grandpa holding me as a baby in 1989. After grandpa retired, he started a side job as a clown, where he’d go to birthday parties and do magic tricks. He also often wore his boxing shorts from his days as a heavyweight boxer at Michigan State. He was dressing up to entertain the grandkids that day, and the boxing/clown combination certainly made for an interesting photo.

#92 My brother put all he had on the dance floor the night of my parents’ 1987 Christmas party.

#93 My family owned an internet service provider when I was growing up, and this was our big promo shot.

#94 My husband was taking pictures the entire time. This is when they started to sew me up, and apparently the most opportune time to take a selfie.

#95 This was taken by a professional photographer for my dance class in the late ’90s. Disney clearly missed out on a star and her power stance.

#96 Having your photo taken with Thomas and Friends seemed pretty simple.

#97 My grandparents in Hawaii in the early ’70s. And no, that’s not grandma on the right. She’s on the left giving the stink eye. If looks could kill, that hula girl wouldn’t live to see her next luau.

#98 In 1998, I was 7, and this was a show and tell. I told my classmates, ‘I went to Africa over the weekend and petted a lion.’ I lied.

#100 Had to renew my driving license; thanks to the idiot that stamped my new license, I’m now Quasimodo.

#101 My sister found these in the reject pile from a childhood photo shoot, but we think these should really have been chosen for the living room wall.

#102 When my husband was a teenager, he got a phone in his bedroom with a caller ID, which at the time was a big deal. This is my husband’s dad in the photo because he wanted some photos taken to show off the phone.

#103 This was me in first grade. My mom convinced me to cut my hair ‘like Demi Moore in Ghost.’

#104 My daughter meeting Ronald McDonald back in 1992 when she was three.

#105 When my father got remarried after my parents’ divorce, my mother went through the family albums and cut him out of all of the family photos. Using scissors became too labor-intensive, so she switched to white-out.

#106 My Italian grandfather on his first trip to Hawaii.

#108 My husband, his mother, and sister. My mother-in-law thought she was being ‘artistic.’

#110 Being a mom isn’t easy so while you try to get one kid to sleep you’re also playing with another.

#111 This is a picture of my wife on our wedding day. I’m not certain how she got her leg to do that, but needless to say she is quite flexible.

#112 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.

#113 Our family is Italian, and one of our favorite traditions has always been having stuffed artichokes on special occasions.

#114 My wedding: August 2004. In what has become known as a ‘family’ thing, men from his side shed clothes as the night goes on. This is me and my husband’s uncle about halfway through our reception at a local restaurant/bar.

#115 My aunt and uncle were crowned ‘Golden Couple’ at our local fair for being the longest married couple in the county at 72 years. Our local paper did a fantastic arrangement for the honor…

My aunt and uncle were crowned 'Golden Couple' at our local fair for being the longest married couple in the county at 72 years. Our local paper did a fantastic arrangement for the honor...

-1 Points
Upvote Downvote

Written by Hannah Jade

I write and compose interesting stories, captivating beautiful moments in photos. I love walking alone in Rainy Nights without an Umbrella.

Leave a Reply

Your email address will not be published. Required fields are marked *