Getting drunk and making questionable decisions — who hasn’t been there? But the stakes are higher when you’re the brother of the future queen of England. Just days after Kate Middleton and Prince William’s wedding in April 2011, old photos of James Middleton resurfaced that showed him engaging in a series of embarrassing acts at a house party. In one, he posed nude covering his private parts; in another, he flashed his naked backside at the camera.

James had shared the pics to social media, but they leaked to the press in 2008 even though he had set his page to private. “These photos were not for the public, they were on his private Facebook profile and someone managed to get in and take them,” a source told Us Weekly. At the time of the leak, attorneys for Michael and Carole Middleton reportedly asked newspapers never to republish the photos, which they obliged, according to the Daily Mail. That wasn’t the first time James found himself in hot water.

Earlier that same year, James went out to celebrate his 21st birthday in a Chelsea nightclub and was photographed drunk, peeing on the street, which is illegal. Michael and Carole, once again, came to the rescue. “Michael had to literally carry James to the car. He was all over the place and couldn’t stand up properly,” the photographer behind the photos told GQ in 2012. The U.K. media never made the images public, but they were published in Australia. 

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