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


Just before their first Valentine's Day together, Simpson and Romo joined Ashlee Simpson-Wentz and her then-boyfriend Pete Wentz for a double date at Dallas's Grand Lux Café on Feb. 13, 2008. The next night, the couple kept to themselves, marking the holiday with a romantic meal at Nove Italiano restaurant. "All eyes were on them," an insider said at the time.