Jewel: The Beginning
Sean Penn and Jewel’s relationship began in 1995 when Penn, impressed by her music, invited her to write a song for his film The Crossing Guard. Jewel was an emerging artist at the time, and Penn’s interest in her talent led to a personal connection.

Their relationship blossomed quickly, with Penn reportedly helping Jewel navigate the entertainment industry. Despite the significant age gap—Jewel was in her early twenties while Penn was in his mid-thirties—their connection was creative and romantic. Jewel later described Penn as kind and supportive during their brief time together.