What’s Your Favorite Awkward Family Photo?

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From braces and bad hair to long forgotten fashion mistakes, we all have photos from our past that we’d just as soon leave packed away in the attic gathering dust.

But thanks to Doug Chernack and Mike Bender, those gawky and goofy pictures can be immortalized on the Internet, providing enjoyment to millions around the world.

These two longtime friends are the brains behind Awkward Family Photos, a super popular blog based on reader submissions of… you guessed it: Awkward family photos.

We had a chance to chat with Chernack about the website, their brand-new best-selling book and why the holidays are such a breeding ground for uncomfortable-looking photographs.

What inspired you to start the website?

“It all started when Mike [Bender] saw an awkward family vacation photo at his parents’ house. It was a ski photo of him and his brother doing a Rockettes pose on the top of a mountain.  He was feeling the pain of that moment and was telling me about it at lunch the next day, and I mentioned that I had a ton of those kinds of photos myself.

That was the spark, so we went back to the house and put a really simple website together and we sent it out to friends and family with the hope that more friends and family would submit.

We got very lucky, very early on because one of Mike’s friends worked for a radio station in Rhode Island and he posted it on the radio station’s website. The next morning we woke up and the link had been passed around to hundreds of radio station websites across the country.

We went from zero hits to a million hits within that first week and it just kind of took off from there. It was crazy. We weren’t prepared for it at all, we had never done anything online, the site was crashing all the time – we were just trying to keep the site up. And that was probably three years ago. So it’s been a real education but it’s been a lot of fun.”

Tell us about the new book

“It’s called Awkward Pet Photos and the idea is that we love our pets so much, and we do so many awkward things with them. The pets aren’t the awkward ones, it’s us.

We give them middle names; we throw them birthday parties. The holidays are a perfect example – we want to share the holiday spirit with them and really the holidays have no meaning to these pets. But they go along with it out of loyalty.

We take them to the mall to sit on Santa’s lap, we dress them up in holiday costumes, we put ornaments around them. And these poor pets are so confused. They’re completely freaked out when they’re sitting on this fat man’s lap at the mall. But again, they go along with it out of loyalty and so the holidays are the best times for the awkward pet scenarios.”

Why do the holidays inspire so many awkward photos?

“We have our theories. I think one of the reasons is that it’s a time when the entire family is forced to be together, and not just for a small amount of time. And add to that the outfits that we are sometimes required to wear and all the pictures that are being taken at these events.”

Do you have any awkward holiday photos in your own family?

“I do. It’s more of a Thanksgiving moment but my wife’s family has a tradition where – believe it or not – they wear turkey hats while eating Thanksgiving dinner. 

I walked in on that when I spent my first Thanksgiving at my in-laws house and I didn’t even know what to say. But they gave me a hat, and it was a very ceremonial tradition and so yes – we dine wearing turkey hats at Thanksgiving.”

Have there been any pictures that are little bit too awkward or inappropriate?

“We definitely have a file that is NSFW. We get some very odd and some very disturbing ones. Water birth scenes, and there’s a whole series of open casket family photos that people submit.”

What’s your favorite awkward family photo on the website?

“My all-time favorite was actually the cover of the first book. It’s a family stacked on top of each other in a pile-on formation and they’re all wearing matching denim outfits. It’s got so many great elements all working together. Their heads are all turned perfectly in alignment. It’s just a beautiful shot on so many levels.

One of our favorite holiday photos is one of a family in matching outfits. It’s a mom and the three daughters all wearing matching pajamas in front of the Christmas tree and the dad is standing completely shirtless in the picture looking really confused about what he’s doing in the photo.”

Want to see more awkward snapshots? Check out the new book, Awkward Family Pet Photos, and visit their website for the full range of quirky, crazy and downright strange family photos. 

In the words of Chernack, “We are constantly surprised by what we get in our inbox.”

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