“Twenty-five years after dummy broke up with me, I married him.  It was the sweetest thing in the world and everyone was excited for us.  His brother Brian agreed to take photographs of us at the local museum.  We took some stunning ones at the front and on the lawn of the offices, but followed the advice of an administrator and went to the North Garden as she said, “That’s where my daughter’s best photos came from.”  I was going through the pictures when I saw I totally blocked my husband out with my big hair.  When I posted it on Facebook with the admonition, “Never marry a woman with big hair” a good friend of mine pointed out the bush in the background looks like a demon.  Needless to say, it elevated this photograph to Super Awkward Status.  Enjoy.”

(submitted by Susanne)

“My mom took my brother and I to a portrait studio when overalls with one strap down were cool.  He was a junior in high school and I was a 6th grader. I don’t know that we’ve ever recovered.”

(submitted by Laura)

“We found this photo and discovered that my brother was a dead ringer for baby Chris Farley.”

(submitted by Shawna)

This was 2004 – and these were my senior pictures. The two boys are my best friends since we were 3 and I thought it would be a great way to memorialize our friendship. Instead they all looked like really bad polyamourous engagement pictures, complete with us holding hands and skipping off into the sunset. Needless to say, my parents didn’t purchase those. We still refer to these as “The Engagement Pics”.

(submitted by Dianne)

“My daughter asked for a “Panda Cake” for her 3rd birthday. Things got a little dark when it was time to serve it.”

(via source)

“My friend managed to make this bubble.”

(via source)

“My uncle had the weirdest wedding.”

(via source)

“Our first date was at the dog park, we came back 5 years later and got photobombed”

(via source)