Jessica's juicy flings, rumored beaus, and serious boyfriends! See which guys were lucky enough to date Simpson through the years -- including ex-husband Nick Lachey, John Mayer, Tony Romo, and former NFL player Eric Johnson.
The singer dated the Supernatural actor in the late '90s around the time she became a household name with her debut album Sweet Kisses. It was rumored that Simpson was speaking of the hunk when she later recalled her "first heartbreak" on an episode of MTV's Newlyweds: Nick and Jessica years later.
Credit: LISA ROSE/GLOBE PHOTOS