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In this bonus edition of "Shot Glass Diaries," Ian tells the story of the weekend he proposed to his then girlfriend, Amy during an all-expenses-paid getaway to the Pocono Palace Resort in 2012. After being gifted this trip by Amy's parents, Ian saw it as the perfect opportunity to pop the question in their exquisite suite while enjoying snowmobiling, games, and participating in an adult-themed version of "The Newlywed Game" in front of a live crowd at the resort.