When Cheri Dennis' debut album came out, both the album and its artist had traveled quite a long road. The Cleveland-born singer had begun her professional career nearly a decade ago, when she was a guest on Mase's 1999 album Double Up. A couple years later, Sean "Diddy" Combs signed Dennis to his Bad Boy Records after she ran into him at a party and staged an impromptu audition. And then... she just kind of sat on Bad Boy's shelf, doing some backing vocals here and there, but not much else. Finally, in 2006, Dennis put out the single "I Love You" and seemed set to release her debut album. But then it got pushed back. Twice. In and Out of Love finally came out in early 2008, and Cheri Dennis, the first woman signed to Bad Boy after Faith Evans, seemed poised to shine.