Awkward School Pictures: an awkward we can all agree upon


From geeks to the obese, home-schoolers to binge-drinkers, Awkward School Pictures (ASP) has captured the classic, cringe-worthy characters of our academic careers. We point, we snicker, we email each other links with subject lines like Check out this freak! Is it high school all over again?

Yes. It is.

And we couldn’t be more pleased.

Awkward School Pictures is the website where bad fashion, thick glasses, and embarrassing obsessions with action figures have come to haunt us. We know these kids. We were these kids. Maybe we still are these kids. And ASP is not going to let us forget it.

I had the indubitable pleasure of learning more about ASP from the creators themselves. Here is what the kings of the uncouth had to say.

This interview was conducted by the Derwood Hunsdale-Talbot, Chief Book Geek and maven of book reviews at Written Word.

Please say all the boring things about your website here and now. This should include, but is not limited to: who you are, when this site was launched, how many user-submitted entries have you had to date, what is your favorite type of sandwich, what was your inspiration to start this site, what was the enduring need for such a contribution to the web that Awkward Family Photos (AFP), Awkward Workplace Photos (AWP), et al. didn’t already fulfill, what are your goals for Awkward School Pictures (ASP), etc.

The website was started by myself (Brian Michaels) and my friend Albert Estevez here in San Diego around September of this year. My favorite sandwich is actually a sandwich hybrid known as a calzone, lol. Albert’s favorite is the Subway traditional sandwich. The reason why we started the site is because we enjoy it and noticed that there wasn’t already a website dedicated to the awkwardness of school. Albert and I jumped on the idea we had while observing some funny kids in a frozen yogurt shop here in San Diego.

What are the top 3 qualities of a successfully awkward picture?

The top 3 qualities of a successful awkward picture are 1.uncomfortable, 2. original, and 3. understandable.

In your opinion, which would qualify as more awkward: a good looking girl in an ugly outfit or an ugly girl in a good looking outfit? Who has the more tragic story life story: the Ugly Ducking or Kristie Alley?

I would say Kristie Alley has the more tragic life story because she had a high point in her career and she has gone all downhill form there (going on Jenny Craig and becoming obese after). It is the exact opposite for the ugly duckling who ended up improving over its lifetime.

If you had to give one of your awkward subjects two pieces of advice, what would that advice be?

Advice for an awkward subject would be 1. BE YOURSELF! 2. Let the cards fall where they may.

On a scale of 1 – Joaquin Phoenix, how awkward would you say you are/were in school?yearbook_laser_effects

I was somewhat awkward in elementary and middle school probably a 5 or 6 on a 1-Joaquin Phoenix scale I don’t know what celebrity to name for that number lol I was a lot cooler in high school and college. Albert was a chubby kid from elementary school to junior high and then in high school he was one of the most popular guys in school and was the lead singer in a well-known local band (basically he became a chick-magnet). At the current moment we are both stud muffins.

In your expertise, during which grade is the average individual the most awkward?

I would say that the most awkwardness is evident in the elementary school years because that is the time in a child’s life when they might have braces or haven’t really figured out their look. This is most likely because our moms were still picking out our outfits and we were still forced to wear hand-sewn sweaters from our grandmothers.

If your website was to have a song playing in the background what song would it be? *Note: the fact that your website doesn’t have a song playing in the background is one of its irrefutable positive qualities.

I think if I had to choose a song to play on the background of our site it would have to be Cyndi Lauper’s “Time after Time.”

Have you ever experienced a picture that is too awkward? If yes, what did it depict? If no, what do you imagine this mythical image to entail?

The most awkward picture I have seen was of a little girl checking her email while sitting on one of child potty trainers; it was a little too weird for the site I believe–even though we are pretty open minded about awkwardness and the pics people send us.


Brian Michaels, thanks for taking the time. School pictures as funny as these should probably be placed on flyers and passed out to thousands of people as they walk through the streets. But that’s just this reporter’s opinion.


  1. This photo is actually from a competition where students could win prizes by making costumes out of duct tape.

  2. Hey i wanted to let you know this site is working really great on my braaand new ipad keep up the good work :D!

  3. OK john three things1. South Park is awesome2. King of the hill is the suckiest suck to ever suck3. If you like King of the Hill and hate South Park, then why are you even on this website

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