After her victory, she recorded a popular duet in 2003, "Un nuovo bacio" with her boyfriend, singer-songwriter Gigi D'Alessio, and also "Il mondo è mio" in 2004. Her first album, Attimo x attimo was released only in September 2003, and contained her first duet with D'Alessio. Success and popularity came in 2005, when her second album, Ragazza di periferia was released. The album, which included numerous songs co-written by D'Alessio, spun a string of hits such as "Quando due si lasciano", "Qualcosa di te", and the titular track. In 2006 she participated in Sanremo's Women Category and won with a new song, "Essere una donna". She followed up this success with 2007's Mai dire mai, her third album.
It was certified platinum weeks after its release and while not being able to match her hit-churning sophomore effort, displayed a newfound maturity in terms of musical direction. It was also the first time Tatangelo penned the lyrics to her own songs, in "Averti qui" and "Lo so che finirà". In 2008, she sang a new song at the Sanremo Music Festival, winning second prize with "Il mio amico", which was dedicated to her best friend Claudio. The song broke away from standard themes of love as it talked about discrimination against homosexuals.
With this song Tatangelo also recorded a duet with American singer Michael Bolton. Tatangelo ended a series of concerts that started in March 2008, in her debut tour. Her fourth album, Nel mondo delle donne, was released on 28 November, and contains 9 new songs and 2 covers. Every song on the album has a theme related to women, the most significant ones being that of spousal abuse in "Rose Spezzate" and the feelings of a woman betrayed in "Va Da Lei". It has been noted for Tatangelo's maturing voice and greater emotional depth in her songs.
On the same day of the album's release, Tatangelo's official fanclub, Tutto Anna, was established online. In Italy the album went Gold, with 50,000 copies sold. In May 2009, news was leaked to "Chi" magazine that Tatangelo was in the second month of pregnancy, the father-to-be being D'Alessio. However, days after, the couple held a press conference to announce that Tatangelo had suffered a miscarriage. Read more on Last.fm.
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