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The 12 most embarrassing photos on the web

A photo can cost you your reputation, your job, even your freedom

A single photo can cost you your reputation, your job, even your freedom - if you post it online. Teachers, principals, firemen, mayors, university presidents and everyday people have all discovered the dark side of putting the wrong photos and videos on social networking sites. The results aren't pretty, but they are sometimes hilarious. Here's our dirty dozen - 12 pictures their owners probably wish they could take back.

10. How not to use Facebook's privacy settings

It was a vacation she'd probably rather forget. When Janet Dudley-Eshbach, president of Salisbury University in Maryland, created an album of her family's trip to Mexico on Facebook in October 2007, she didn't expect a local TV station to broadcast the photos to the world, or to have a Wikipedia entry covering the mini-scandal.

The problem wasn't the photos so much as the captions, like the one for this picture: "I ended up having to beat off the Mexicans because they were constantly flirting with my daughter." (We believe she meant with a stick.) Or the photo of a tapir, a piglike mammal, with an arrow pointing to its outsized manhood. The 53-year-old educator was forced to apologise for conduct unbecoming a university president -and to endure a painful lesson on how not to use Facebook's privacy settings.

11. Yesterday, Spring Break; Tomorrow, Prison Break

What's a Halloween costume cost? For college junior Joshua Lipton, it was two years of his life. In October 2006, the Bryant University student was charged with drunk driving after causing a three-car crash that left one Providence woman in critical condition. Two weeks later he showed up for a Halloween party dressed as 'Jail Bird', photos of which made it onto Facebook. That didn't sit very well with the judge in the case, who called the picture "a defence attorney's worst nightmare" and sentenced Lipton to two years in prison. The good news: the department of corrections didn't have to issue Lipton a new jumpsuit--he already had his own.

12. I'm a PC, She's a Mac, and You're Unemployed

Michael Hanscom did not pose nude on Flickr, attack the locals with a stick on his trip to Mexico, or dress up like the Fairy Princess while calling in sick. His crime? In October 2003, the Microsoft temp posted photos of Mac G5s being unloaded on the Redmond campus to his blog with the title 'Even Microsoft wants G5s'. And that was enough to get him sacked from his job in Microsoft's print shop for an alleged "security violation". Apparently, the world's largest developer of software for the Mac (besides Apple) didn't want anyone to know that some of its employees use Macs. (Thanks for Michael Hanscom for use of the photo.)


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