Backstreet Boy Howard "Howie" Dorough got more than he bargained for after hiring Leigh Boniello to be the band's webmaster in December 2000. Boniello went on tour with the group and quickly grew close to Dorough.

Six years later, the couple attended a New Year's Eve party at the New Jersey home of Boniello's father. "I figured, what better timing," says Dorough, "because all of her family was going to be there, including her 92-year-old grandmother." Just before the stroke of midnight, Dorough made a toast and presented Boniello with a custom-designed three-stone diamond engagement ring.