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In 1997, Shakira founded the Pies Descalzos Foundation. It is a Colombian charity with special schools for poor children all around Colombia. It was funded by Shakira and other international groups and individuals. The name of the foundation is taken from Shakira's third studio sex wallpaper 1600x1200 album called Pies Descalzos, released in 1995.

In 2000, Shakira started dating Antonio de la Rúa, the son of then president of Argentina Fernando de la Rúa, a romance that made headline news throughout Latin America. In March 2001, he proposed to her. De la Rúa and Shakira remain engaged.^[31] She currently lives in The Bahamas. Shakira's future mother-in-law Inés Pertiné claimed the wedding would take place in September 2007 in the mansion which Shakira owns in the Dominican Republic (though this didn't happen). She also said that Shakira has caria already ordered Argentinian designer María Pryor to design her wedding dress,^[32] All this was denied by Shakira herself in Mexico.^[33]

In 2001, upon the success of ¿Dónde Están Los Ladrones? and MTV Unplugged, Shakira began working on a crossover album to English. Collaborating with Gloria Estefan, she wrote and recorded English versions of the tracks from ¿Dónde Están Los Ladrones?. However, she later decided against using translations of older songs for the album and worked for over a year on new material for the album. Around this time, Shakira also released four songs for Pepsi and for her promotion in the English markets: "Ask for More", "Pide Mas", "Knock on My Door" and "Pideme El Sol". In November 24, 2001, Laundry Service was released, although Shakira chose to exclude the four Pepsi songs. Although it was created with the intent of selling to an English language market, the rock and Spanish dance-influenced album also featured four Spanish songs, including "Que Me Quedes Tú" ([I hope] that you remain (for me)). Some critics claimed that Shakira's English skills were too weak Shakira sexy for her to write in it. The album sold extremely well and was certified triple platinum in the US (denoting sales exceeding 3 million copies)^[18] and thus helped to establish Shakira's musical presence in the mainstream North American market. The album has sold approximately 13 million copies worldwide.