Jessica & Tony: The Way They Were

From double dates with Ashlee & Pete to dirty dancing in the club, look back at the couple's down-home romance


Despite reports of a split, Romo was a doting date to Simpson at little sis Ashlee's wedding to Pete Wentz on May 17, 2008. "They were cute," the bride said of her maid of honor, who dirty-danced with Romo at the Alice in Wonderland-themed reception.