Win $500!!!

In anticipation of the upcoming movie The Way Way Back, a new comedy from the studio that brought you Little Miss Sunshine and Juno, we invite you to share with us your own awkward vacation photos! Dust off your old photos and give us the most awkward vacation moment you've had with your friends or family. Submit your entry and get as many of your friends and followers to repin and like your entry on Pinterest. We will shoot you an email once your entry has been accepted, so don't forget to keep an eye out for it, and share the link to your pin with as many people as possible. The participant with the most repins and likes wins a $500 Visa gift card!!!

The Way Way Back opens in theaters nationwide this July 5th! Check out the trailer and get your tickets now: http://bit.ly/11S4Sou

How to Enter

  1. Start your entry using the Enter Now button above.
  2. Upload your most awkward vacation photo and tell us why your vacation photo is the most awkward.
  3. Follow Fox Searchlight on Pinterest. http://pinterest.com/foxsearchlight
  4. Once approved, you will receive an email with the link to your pin on the official contest board http://pinterest.com/foxsearchlight/awkward-vacation-photos-contest
  5. Share your entry with friends on Facebook, Twitter, or over email because the entry with the most Pinterest repins and likes wins!
  6. Don’t forget to check the leaderboard on this site for contest leaders (updated daily).


  • (1) Grand Prize – $500 Visa Gift Card
  • (1) 1st Place – $75 Visa Gift Card
  • (1) 2nd Place – $50 Visa Gift Card
  • (3) Referral Drawing – $50 iTunes Gift Card

* Submissions accepted Jun 21, 2013 12AM EST through Jul 7, 2013 11:59:59PM EST only. Previous Grand Prize winners of any ShareRoot contest from the previous 6 months are not eligible. Open to U.S. residents only. REPINS AND LIKES FROM YOUR OWN ACCOUNT OR FAKE ACCOUNTS WILL NOT BE COUNTED AND YOUR ENTRY MAY BE REMOVED.

For complete details please see the Official Rules.


   182 repins & 181 likes

In Gatlinburg traveling down on a trail from a waterfall, my 16 year old son decides to "FLIP" over this railing moments after I snapped his picture sitting on this railing and warning him to get off of it! It was very awkward not to mention hilarious! // cathy M. #TheWayWayBack #PinToWin

   140 repins & 128 likes

We were visiting family in Eastern Washington. My Uncle gave us a tour of the jail & we walked into a cell & saw this..very gross & awkward. he looked embarrassed as he thought it had been cleaned up since no one was in it // debbie N. #TheWayWayBack #PinToWin

   90 repins & 107 likes

This is my awkward vacation photo because I'm just standing there while my friends are in a group talking. // Kenny F. #TheWayWayBack #PinToWin

   95 repins & 77 likes

Several drinks later…. // Laurie S. #TheWayWayBack #PinToWin

   6 repins & 11 likes

What happens Up North stays Up North? The three wives were wondering what really goes on during their drill weekends… I had manage to take a photo of the guys just at the right time and the placement of the hands had us laughing for hours. The 6 of us (three couples) were spending a weekend together before these three guys deployed out. // Michelle N. #TheWayWayBack #PinToWin

   8 repins & 7 likes

While on our honeymoon, we went into a retail store and my husband decided to jump on an exercise bike! // Amber C. #TheWayWayBack #PinToWin

   8 repins & 5 likes

Trying to be sexy for the wives! // Leah J. #TheWayWayBack #PinToWin

   7 repins & 6 likes

"Is there room in there for me?" Giraffe stuck his head inside the car window. I couldn't believe his neck stretched that far. // Tricia F. #TheWayWayBack #PinToWin

   5 repins & 6 likes

My first vacation EVER with my daughter and me with Elvis. This is extremely awkward because Elvis' stiff, razor sharp hair was poking me in the side of the head the entire time. I was just trying to keep it away from my eyes to keep from being blinded. #TheWayWayBack #PinToWin // Sherry G. #TheWayWayBack #PinToWin

   2 repins & 7 likes

This is the most awkward family vacation photo, because we were not ready for the picture. One of our eyes were closed, we were looking in the wrong direction and talking. Just awkward and off guard. We had fun though. // Tyra S. #TheWayWayBack #PinToWin