“In the fall of ’85, when I was a junior in high school, a new, slick student asked me to go to Homecoming. I was smitten and immediately said yes. After my mother bought me a rather expensive (and fluffy) dress, the slick boy of my dreams asked someone else and dumped me. I was embarrassed and heartbroken. A few days later one of the nicest and most popular seniors in the entire school asked me to go to homecoming in the hall. While it was painfully obvious that he had been roped into it by a parent or my bigger brother, I agreed to his self-sacrifice. We ended up double-dating with one of the girls in my class and her senior boyfriend, and I had a wonderful time. He even kissed me good night, in that polite, “you weren’t a bad pity day” sort of way that good guys do.

John, wherever you are, you were my red-headed knight in shining armor. And sunglasses. So no one knew it was you who was with me. I bet you turned out wonderfully.”

“My father and his soon-to-be-wife. There is no explanation needed.”

(submitted by Hannah)

Everything he did, he did for his family.

(submitted by Regina)

“Me with my two brothers in 1968. We just moved to Switzerland  where my father got a good job with a much better salary than before. So we were showing off a new bicycle, a new scooter, new clothes, and my mother’s impeccable sense of fashion.”

(submitted by Gautier in France)

“This is my little sister in costume for her dance routine to the Village People’s “Macho Man” song. The sad part is, someone put a lot of effort into creating this monstrosity, and what’s worse, made her wear it.”

(submitted by Celia)

“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 he got in the face! All of this right on the front steps of a church.”

(submitted by Debbie)

“We had the worst wedding photographer in the world. I think this says it all.”

(submitted by Amy)

“Every summer, we drove from Southern California to Iowa. Every summer, the car broke down.”

(submitted by Ginger)

“My father, brothers, and I in 1983. The sad part is it wasn’t planned that way. We all just showed up dressed so poorly.”

(submitted by Steven)

“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.”

(submitted by Devon)