Here's a shocker - Jewel and Sean Penn dated.

In her new memoir, "Never Broken: Songs Are Only Half the Story," the 41-year-old songstress shared some juicy details on her pre-fame relationship with the two-time Oscar winner, who reportedly sought her out with a phone call to her father in Alaska after watching her television debut on "The Conan O'Brien Show" in 1995.

The "I Do" singer recalled knowing "nothing about glam squads" and going on stage wearing "purple polyester pants with a black T-shirt and a tacky belt with a rainbow buckle."

On the heels of 1995 debut album "Pieces of Me" - which became one of the highest-selling breakout records of all time - Jewel returned home to Alaska to learn about the odd phone call her father (now a star of Discovery's "Alaska: The Last Frontier") received. Lucky, Penn called back a second time.

"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 wrote, according to PEOPLE.com. "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."

The romance reportedly began while Penn was on a break from his now second ex-wife Robin Wright - this was before Penn and Wright got married and had two children together, Hopper and Dylan.

Jewel and Penn eventually met up at a salon in San Diego, where she was getting her haircut and Jewel ended up writing a song called "Emily" for Penn's movie. During their time together, she insisted that the two secretly fell in love, speaking on the phone and flirting religiously with one another, but Jewel admitted that she had to keep her guard up with Penn.

"I was no fool and knew I was most likely a trifle to him. I intended to give him no such conquest," she wrote. "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.... I moved very slowly with him but he was a persistent and inventive suitor, and I enjoyed it immensely. I kept our burgeoning relationship very quiet (keeping her relationship out of the public eye)."

Jewel admitted that she loved Penn better when he wasn't drinking, so she asked him to stay sober, writing, "I liked his mind sober and had fun playing this way. When I told him this in all seriousness, in a dive bar after a sound check, he responded with a melancholy stare and then canary-eating grin and said it would be impossible not to fall in love with me. I looked at him to see if he was serious. It seemed he was."

During their time together, Penn introduced Jewel to the likes of Jack Nicholson and Warren Beatty. The two even attended the Venice Film Festival together, where Penn introduced her to his glitzy and glamorous world, which she enjoyed but felt she could never be a part of.

"Sean would whisper in my ear and explain everyone's backstory to me. It was not my world and I was pretty sure it never would be. Sean took me to see the sights in Montartre and wrote me in notes that he hid in my pockets," she said. "I enjoyed Sean and would eventually fall in love."

Their romance eventually faded and the two split later that year.

Penn reunited with Wright and the two married in 1996 before divorcing in 2010. Earlier this year, Sean split from supposed fiancée Charlize Theron. Jewel married rodeo star Ty Murray in 2008 and the couple had one child, four year old Kase, before splitting in July 2006.

On Monday, Jewel discussed her and Penn's relationship with Howard Stern, telling the outspoken radio host, "It was hard on me. He really believed in me at a time when nobody else did. And he really made me feel good about myself and I was so desperate for that. Having that go away was hard."

Meanwhile, Penn made national headlines on Tuesday for filling a $10 million defamation lawsuit against "Empire" creator Lee Daniels for reportedly comparing Terrence Howard to him in a domestic violence case.