Mariah Carey and Nick Cannon
Asking someone to marry you is tough. Asking Mariah Carey to marry you is, well, tougher. So imagine the nerves when Nick Cannon asked Mariah Carey to be his wife not once but twice within 24 hours. The first proposal happened on a New York City rooftop where Cannon got down on one knee and presented Carey with a candy ring pop - with a real diamond ring inside. Carey safely recused the 17-carat emerald-cut diamond ring from the lollypop, and the next day, just in case the first proposal wasn't romantic enough, Cannon proposed again while the couple were on a helicopter tour of the city, right over the Empire State Building.