Christina Milian

• 2005–06: So Amazin '​ and record departure
Whereas Milian's previous albums had pop stylings, she was encouraged by Island Def Jam to target a new audience and release an urban record. Explaining the change, Milian said that one of her main problems was that previous releases would often find mainstream success, but would be relatively unsuccessful on urban radio. As an R&B artist, she wanted to build her core audience–a true fan base that would support her through time–to increase her career's longevity. The main purpose of her genre change was to go back to the streets and add to her core audience. To create a more urban record, Milian had a list of producers that she wanted to work with. L.A. Reid suggested to Milian that she should work with Cool & Dre, with whom she ended up working with as the first people to start off the album. Although Milian was originally supposed to work with several different music producers, she felt that the chemistry they had in the first week was so "instant and real" that she felt she could not get a better "vibe" with anybody else other than them. Milian ended up working with Cool & Dre on the majority of the production of the album, producing ten of the album's eleven tracks together. The album completed within a three-month period, whereas Milian's previous albums would take six months to a year.
Milian's third studio album, So Amazin', was released on May 16, 2006. The album's lead single, "Say I", featured rapper Young Jeezy. The single saw peak positions of number four in the UK, and number 21 in the US. So Amazin '​ debuted and peaked at number eleven on the Billboard 200 albums chart, selling 54,000 copies in its first week and 163,000 copies in total. Internationally, the album peaked at number 55 on the Swiss Albums Chart, 67 on the UK Albums Chart, and 139 on the France Albums Chart. Reviews of So Amazin '​ were mixed; critics felt that while Milian claimed that she was displaying the various sides of her personality, the album could "only scratch the surface of who she really is." "Say I" was praised by several critics, and was described as "instantly rousing" and "intoxicating". In June 2006, Milian's representative confirmed that she had been dropped by Island Def Jam. In an interview with Rap-Up, Milian revealed she was dropped a week after her album was released. The singer believed it was a "budget cut", and that Island Def Jam Music Group wanted to spend more money on label mate Rihanna. She said, "it was embarrassing. It was a week after my album got put out. I would be in my room a lot of the time crying by myself." After leaving Def Jam, Milian released her first compilation album, The Best of Christina Milian (2006).
After the production of So Amazin '​ in 2006, Milian began dating Andre Lyon from the production group Cool & Dre. The pair dated until February 2009, when they decided to go on a break. Milian said that they were still really close, and decided to break up because it was "hard to grow together when you live on two different coasts". The singer wanted to take more opportunities and learn more about herself, which she often let go when in a relationship, but felt that she was in a now-or-never situation. Milian described Lyon as an amazing guy, and said that although there was a chance for the couple in the future, she needed to focus on herself.