Jessica Ann Simpson began dating 98 Degrees group member Nick Lachey in 1999. After dating for two years, the couple cooled their relationship. After the September 11 attacks, the couple reconciled. Simpson stated, "After 9/11, I knew that I never ever wanted to be away from Nick ever for the rest of my life." On October 26, 2002, Simpson married Nick Lachey. She famously announced she had remained a virgin until her marriage. In November 2005, after months of tabloid speculation, Simpson and Lachey announced they were separating.
Simpson filed for divorce on December 16, 2005, citing "irreconcilable differences." The couple's divorce was publicized worldwide and was reportedly finalized on June 30, 2006.

Simpson told Jane magazine in October 2006 that she knew her marriage to Lachey was over when he refused to join her on a charity trip to Africa, even though it was on their third wedding anniversary.

The couple sold their Calabasas mansion, in which Newlyweds was filmed, to Malcolm in the Middle star Justin Berfield for an undisclosed amount. On February 6, 2007, the Associated Press reported that Simpson said she was stung when her ex-husband jumped back into dating after their high-profile breakup. "Oh, it hurt me," Simpson stated in an interview in the March 2007 issue of Elle. "Two or three weeks later? Yeah, I'd say it kind of hurt me."

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