When I was sitting at the Dulles airport waiting for my flight back to Los Angeles at the end of my last business trip, the Virgin America employee at the gate told us about an awkward family photo contest that the airline was holding. She told us that anyone who submitted an entry would get a 33.3% discount on their next ticket purchase. Sounds good, right? I thought so, so I figured it would be worth my time to dig up an awkward photo (so many to choose from!) and send it in. In order to avoid embarrassing anyone but myself, I chose the picture above. This photo was taken in April 1991 at the Air Force Museum in Ft. Walton Beach. I was twelve years old and my family was there on vacation with my grandparents. I would like to point out that my Mom looks beautiful, but don’t I just look like the epitome of an awkward pre-teen? I’ve never been fashionable, but my outfit in this picture is quite possible the worst ever. The folded over blue socks, the long red shorts, the hideous American flag t-shirt, and that blue hair bow! Yikes! And the frosting on the cake is that I’m very unattractively squinting in the sun as well. Looking at this photo makes me cringe so I submitted it to Virgin America’s contest hoping to use my 33.3% discount to buy a ticket to see Käthe in Seattle sometime next year. It was only after I hit “submit” that I discovered that the discount only applies to purchases of 3 to 6 airline tickets, and since I’ve never bought more than two at once, there was no way I would be able to take advantage of it. That was a detail that the Virgin America gate attendant failed to mention when I was at Dulles or I wouldn’t have bothered. The upside to all of this is that I’ve found quite a few other awkward photos to embarrass each and every member of my family – take a look at the six top contenders that I’ve scanned and posted here.