Inside Jewel’s Relationship With Sean Penn — ‘He Was a Fantastic Flirt’

Singer/songwriter Jewel has written a lot of songs about love and heartbreak. She hasn’t had that many relationships along the way, but it’s clear that the connections have been meaningful. She’s gone out with a few celebrities, and one of the men she has reportedly dated is Sean Penn, and he still seems to have a special place in her heart. 

Jewel’s musical life

Jewel headshot, looking forward with her hair down
Jewel | Gregg DeGuire/WireImage

Jewel’s childhood in Alaska was unusual, but it prepared her to become the artist she is today. According to Biography, both of her parents were musicians, and by the time she was six, she was performing alongside them on stage. When her parents divorced, she still sang with her father for years, learning from him how to yodel, which would turn up later in her music. 

Jewel started performing on her own at 15 years old. The same year, she won a scholarship to attend a private performing arts school in Michigan. After school, she moved to San Diego to pursue music. She developed a large following singing in local coffeehouses, which eventually led to a contract with Atlantic Records. 

Her debut album, Pieces of You, was released in 1995. It was slow to gain attention at first, but finally became widely recognized the following year, becoming one of the highest-selling debut albums ever. She went on to release over a dozen more albums, selling more than 30 million worldwide. 

Relationship history

According to Ranker, Jewel hasn’t had very many relationships, largely because she was with Ty Murray for 16 years. The couple dated for over a decade before they married in 2008. Their son, Kase, was born in 2011, and three years later the couple divorced. 

Since a year after the divorce, Jewel has been dating Charlie Whitehurst, a quarterback with the Indianapolis Colts. 

Other than a short relationship with soap opera actor Christopher Douglas, Jewel has only confirmed one other relationship in the years before her marriage. In 1995, she and Sean Penn dated for a while after he separated from Robin Wright for a while. The relationship didn’t last, and Penn and Wright reconciled and later married.

But although Jewel and Penn weren’t together long, it left a lasting impression on her. 

Falling in love with Sean Penn

US Magazine reports that in 2015, Jewel released a memoir, called Never Broken. In it, one of the things she reminisced about what her relationship with Penn.

It started in 1995, shortly after the release of her first album when she was just starting to get noticed. Penn saw her perform on Conan O’Brien’s late-night talk show. He was impressed, and he called her to ask her to write a song for a movie he’d written.

She agreed, and they met to discuss the project. The connection was immediate. 

“We spoke on the phone a lot and he was a fantastic flirt and I did not mind one bit,” she said. Jewel was certain that Penn wasn’t seriously interested in her, but he seemed determined to prove her wrong about that. 

“I put that man through his paces and he took it in stride. He began to court me in earnest, following me around on tour, acting as my de facto roadie,” she said. “I moved very slowly with him but he was a persistent and inventive suitor, and I enjoyed it immensely.” 

Penn showed a serious interest in Jewel, agreeing not to drink alcohol during their relationship, and supporting her growing career. But the relationship didn’t last the year, and she said it was hard to let him go. After all these years, the memories still appear to mean a lot to her.