The singer opens up about Penn's persistent courting in her new book
Credit: Jeff Kravitz/Filmmagic; Andrew Toth/Getty

After Madonna and before Charlize Theron, Sean Penn worked hard for Jewel‘s heart.

The singer, 41, details her short-lived relationship with the actor, 55, in her new book, Never Broken: Songs Are Only Half the Story, out now. Jewel was on her rise to fame when she met Penn in 1995, the same year her debut album Pieces of You was released and one year before he reunited with and married Robin Wright.

Jewel caught Penn’s attention with her first TV break on Late Night with Conan O’Brien. After putting on a show without the help of stylists – “I knew nothing about glam squads,” Jewel writes – she took a break from the road at home in Alaska. That’s when she got the call. “One day my dad came to find me, saying, ‘Jewel, you must be getting some kooky fans out there in the Lower 48. Some guy just prank-called and said he was Sean Penn,'” she recalls.

Penn was persistent. He called back a second time and managed to convince her dad Atz Kilcher, now a star of Discovery’s Alaska: The Last Frontier, to put her on the phone. “The voice was unmistakably Sean Penn’s,” she writes in the book. “He had seen me on Conan and was working on a movie he’d written called The Crossing Guard. He wanted me to compose a song for it. I told him I would and he said he would meet me anywhere to screen the movie, I could name the day. I gave him my cell number and figured I would never hear from him again.”

However, Jewel soon met Penn and found him “charming, witty, and bright,” noting how their “instant verbal sparring characterized our friendship for the next year.” He was a “fantastic flirt,” but Jewel decided to make him work for her attention. It worked. “He began to court me in earnest, following me around on tour, acting as my de facto roadie,” she writes.

The majority of their relationship “wasn’t spent at Hollywood parties, but on the road,” making it easy for her to keep it under wraps. “I was determined not to be ‘discovered’ because I was dating someone in the public eye,” Jewel writes. After she explained this to him and said she “liked his mind,” Penn said it “would be impossible not to fall in love with me.”

When it was time to promote his movie and her song, "Emily", the couple traded life on tour for the glitz of Venice Film Festival. Still, Jewel “didn’t want to walk down a carpet with him, and he said I could walk it on my own as songwriter for the film, which seemed okay.”

During their time together, Penn introduced Jewel to the likes of Roman Polanski, Jack Nicholson and Warren Beatty. No matter the company or environment, she found Penn respected her artistry and intelligence. “He enjoyed putting me in situations that brought out the best in me,” she writes, “and he never ridiculed what was still so half-wild and messy about me.”

Jewel went on to marry cowboy Ty Murray over a decade later in 2008 and give birth to their son Kase in 2011. The couple announced plans to divorce after six years of marriage last July.

Penn and Wright have two children, Dylan and and Hopper, and divorced in 2010.

As Jewel promotes her new book and album Picking Up the Pieces, Penn has been showing support for another famous ex – the actor was spotted at Madonna’s concert in New York City last week, during which she sang a song dedicated to him. He later filed a $10 million defamation lawsuit against Lee Daniels, claiming he was falsely accused of domestic violence.