After dating for a couple of years (during which the uber-romantic Will did things like arrange for a truck full of flowers to be delivered to Jada on her movie set), Will Smith and Jada Pinkett were engaged in November 1997. "One day we got engaged, and the next day we found out we were pregnant," Jada said. They planned their dream wedding in record time, and on New Year's Eve 1997, in front of 100 friends and family, Jada and Will said "I do" at the Cloisters, a medieval-style mansion near Jada's hometown, Baltimore. The two wore complementary champagne-colored Badgley Mischka designs, and during the reception, Will sang his hit single "Gettin' Jiggy Wit It" along with son Trey.
(Pictured: The Cloisters, site of Will and Jada’s 1997 wedding.)