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She attended Torrey Pines High School in neighboring Carmel Valley.
Around the age of 15, Prettyman was given a mix tape of Ani Di Franco's music.
Were you friends back then, or was that the beginning of your relationship?
We met years before that, and we were actually dating when I recorded that record.
She was signed to Virgin Records until 2013 and released her first major label album Twentythree on August 2, 2005, followed by her second album Hello which was released on April 15, 2008.