Jewel Details Ex Sean Penn’s Flirtatious Ways: He Was “Incredibly Sweet”

Jewel and Sean Penn
Jewel opened up again about her "flirty" past relationship with Sean Penn on Monday, Sept. 28 Jennifer Lourie/Getty Images; Jason Merritt/Getty Images

No foolish games here. Jewel only has fond memories of her past romance with Sean Penn, which she reveals in her memoir Never Broken: Songs Are Only Half the Story. The country singer opened up about their flirtatious past once again during an appearance on Access Hollywood on Monday, Sept. 28.

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“He’s very bright, and it’s just a lot of verbal sparring, which to me is flirty. I’m not a normal flirty person,” Jewel, 41, told co-hosts Billy Bush and Kit Hoover, while also sharing throwback photos of the exes. “To me, verbal sparring is very, very enticing and he’s very bright.”

Jewel and Sean Penn
Jewel and Sean Penn

As detailed in her book, Jewel and the Oscar winner, 55, met when the actor asked her to write a song for his 1995 movie The Crossing Guard. At the time, Penn — who was separated from his future second ex-wife, Robin Wright — reached out to ask the then-unknown songstress for the favor.

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“I was 20 or so, something like that, and my dad thought it was a prank caller and hung up on him several times,” Jewel mused Monday. “He had to keep calling back.”

And luckily, she finally picked up! Penn quickly took her under his wing and showed her what the Hollywood lifestyle was like. The two traveled to Paris and Italy together, and Penn even introduced her to Jack Nicholson — who invited her lingerie shopping. (OMG!) Jewel politely declined, but said yes to the idea of Penn following her on tour.

Jewel and Jack Nicholson
Jewel and Jack Nicholson

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“He wasn’t flirty right away, he was business. We were talking about music and writing a song,” she said on Access Hollywood. “Sean was very sweet. And it was a time in my career when nobody believed in me. I was selling two records every five months and it was just a really rough time. But he really believed in me, and having that really meant a lot. And he’d follow me on tour, and carry my guitar for me. Just incredibly supportive and incredibly sweet.”

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