“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.”

“‘It was here a minute ago!’ My kid searching for his lost lollipop.”

Is this someone’s grandma with Leonardo DiCaprio? Why yes… Yes it is. “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.”

“This is one of my baby pictures. That’s me being held by a person in a Dalmatian costume who is also holding an actual Dalmatian. I have begged my parents for a backstory and all my mom will say is, “I don’t know what you are talking about! This photo is brilliant! I’m brilliant!”

“The only baby picture I have. Why?” Because this is the only baby picture you need!

“What started as a joke Father’s Day gift picked up from a yard sale became our daughter’s best friend. She strolls him around in her baby stroller, sleeps next to him every night and insists he be tucked in with her.”

“My Mom’s 1976 Halloween costume sure was classy.” Classy and cool. They sure don’t make ’em like they used to!

We’re not exactly sure what’s going on here. Should we be scared of grandma now? Is it staged or did we just walk in on something weird?

“This is my son. That’s me next to him. Apparently, enchiladas make you tired.”

“We were trying to work the self timer for a family Christmas photo. The timer went off a little sooner than expected.”

“This picture was taken in kindergarten in the post Soviet 90s when it was popular to take different kinds of costumed school photoshoots. I came home and showed my mom the photo and she said, ‘Oh honey, why aren’t you smiling?’ I thought I was smiling!”

“This is me at my 9th birthday party… apparently, it was laundry day as well. My best friend hit me in the face with a mini-golf putter at the Dairy Queen. It was an accident. Only two friends and my brother were still around for cake after I got home from the hospital. Really Mom, were there no clean shirts around?”

“This is a picture of my breakdancing club. It’s origins are from Bellerose Queens, NY. It’s the late 1980s when breakdancing was a thing. If this doesn’t qualify as awkward IDK what does.”

“The children’s school wanted a picture of our family.” Well, clearly, their family did not want a photo of themselves.

“Here’s a photo from my 3rd birthday in 1980. It was quite the party judging by all that champagne I’m eyeing.” Where’s the ashtray?

“This is my daughter posing for a picture at the Cape May Zoo. We had no idea what was behind her.”

“This was taken after church one Saturday. My parents look like they don’t want to be there. My Uncle looks like he’s surprised to be there, (which might explain why he’s holding a folder), and me and my brother are just there.”

“My mom had the idea to photoshop us all on a ‘mushroom log’ one year, which required a lot of green screen editing. We sent this out for our Christmas card that year.”

“I took a picture of the moment my two kids realized all the donuts at the party had been eaten while they were off playing on the swings.” We feel you, kid. We do.

“This cringeworthy shot was taken at my Uncle’s wedding. I’m on the far right, then my dad, grandfather, and uncle and for some reason, the photographer had us try to look intimidating. Well, I’m a photographer now and do a much better job preparing my subjects for a wedding photo.”

“I asked my dad why he grew it like that he just said that he saw a Led Zeppelin album with old soldiers on it and one of the soldiers had a mustache like that so he just copied them. Needless to say, my mom hated the mustache.”

“My mom said my sister and I were going to Disney. It was actually a resort in the neighboring town.” Close enough!

“This was supposed to be a cute photo of me and my newborn son in 1997.” We’re not sure it’s cute… It seems more scary if anything.

“This is the celebration of one of my cousin’s first communion. Sandwiches, chips, Pepsi, and cigarettes for everybody. My grandma looking proud in the background. What a wonderful time! Madrid, Spain, late 70s.”

“My buddy Josh and his older sister and brother when they were little guys. Apparently when the photographer saw all the prints from the photo shoot, he gave this one to his mom for free because it’s just so hilarious. He would hide it from me when I went to his house because I would cry from laughing at it so much.”

“This is one of my favorite relics of childhood. ⁣Bottom left: my sister laughing at me bc I kept crying).Bottom right: my aunt.Upper right: my dad equally amused at my TOTALLY RATIONAL FEAR holding clearly traumatized me.Upper left: some friend of my dad (idk his name) who was a state fair clown. ⁣⁣Is this a great state or what?”⁣

“Here is a picture of me and my younger brother on Halloween. My brother got sick and was not allowed to trick or treat. I was able to go and my brother was clearly not happy about it.”

“My 14 year old daughter forgot it was school picture day. Normally would have fixed her hair and dressed nice. On this day she wore a Nike shirt that said ‘Just Do It.’ Good thing for us, her hair covered the rest of the shirt and left STD!”

“Me being an Uber Goth teenage posing next to tombstones unknowingly covering the ‘S’ in ‘Sweeney.’ Kind of ruined the mood of the photo!”

“I think this was during a passport photo session in about 1964. I’m the one crying. My dad had just fussed at us for something because he wanted to get the picture over with, and threatened to take it with me crying. Which he did, and which made me cry even more.”

“This lovely picture of my daughter in an adorable outfit. Didn’t notice the graffiti on the sidewalk behind her.”

This was this person’s grandpa when they pulled up into his driveway. We don’t know about you, but if we saw this when we pulled up we would be very scared. Ha!

“According to my mother, my little brother was terrified of the stuffed animal that the photographer was using to attempt to get him to smile.”

“Who makes three siblings commemorate their headgear wearing days? My mom, that’s who! What teenagers agree to have a professional picture taken in said headgears?! My crazy family! Embracing the weird!”

“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.”

“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.”

“My dad in a cow-milking contest before a baseball game, 1977.” You know, just guys being dudes. A totally normal occurrence.

“My mother decided it was cheaper to pose all of us together with our hobbies. Still trying to figure out why my youngest brother was wearing a German outfit.”

“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.”

“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.”