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


While making headlines (and even a cover of PEOPLE) for her recent weight gain, Simpson and Romo (on Feb. 13, 2009) celebrated this past Valentine's Day at New York City hot spot Waverly Inn and capped off the night with dessert at Serendipity. Simpson, who played a show in the Big Apple the day before, told the crowd at the time: "There is something about being in love, right? It just makes you appreciate every day, right?"