In 2006, Simpson began a relationship with Fall Out Boy member Pete Wentz, which gained much media attention. Following her appearance as Roxie Hart in the West End production of Chicago, Simpson announced that she had begun working on her third studio album. The album differed from the pop-rock sound of her previous efforts, featuring a dance-pop and 1980s themed sound. Bittersweet World was released in 2008 to positive critical reception, but it saw a decline in sales for Simpson. The effort reached number 4 on the Billboard 200, and went on to sell 126,000 copies by 2009. Simpson announced her engagement to Wentz in April 2008, with the pair wedding the following month. Two weeks after the wedding, Simpson announced her pregnancy, thus ending promotion of Bittersweet World. Simpson and Wentz had a son in November 2008. The following year, Simpson joined the main cast of the Melrose Place revamp, which was met with harsh critical reception. She later portrayed Roxie Hart in Chicago on Broadway.
Simpson announced her separation from Wentz in 2011, citing irreconcilable differences. Despite having taken time to focus on being a mother, Simpson announced a fourth studio album that same year. She independently released the single "Bat for a Heart" (2012), though it failed to have success. Simpson has since scrapped the album, and focused on her child. She began dating actor Evan Ross in 2013, with the couple marrying in August 2014. Months later the two announced that Simpson was expecting a second child, and in July 2015 she gave birth to a baby girl.
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Sure, the A-Yo singer's concert series was only three shows longs… but she successfully closed out her Dive Bar Tour at The Satellite in El Lay Thursday night!