Jessica Simpson and Nick Lachey (2002-2006)
At the height of their pop success, Jessica Simpson and Nick Lachey were in a high-profile relationship. Jessica was famously holding onto her v-card until marriage, and Nick was the first to marry her on October 26, 2002. The two went on to showcase married life on the reality show Newlyweds, but by December 2005, the pair had separated. Nick is now married to Wipeout host Vanessa Minnillo, and Jessica is engaged to ex-NFL player Eric Johnson — and pregnant with their first child!