Jean-Claude Van Damme
Following Jewel's 1997 romance with Van Damme, she went on to date actor and model Christopher Douglas for a brief period. Per reports, they met through their friendship circles in Hollywood and dated afterward.
Although unconfirmed, they kept what they had a secret, just like what he had been doing with his other partners.
Jewel shared one of her high-profile relationships with Sean Penn, who initially approached and asked her to create a song for his film The Crossing Guard.
Like her past relationships, Jewel kept the details of her relationship with Penn a secret not until she wrote about it in her memoir, Never Broken. She recalled in the book how her father, Atz Kilcher, put her on the phone when Penn called.
She eventually branded him a "fantastic flirt" amid their friendship until it became something intimate.
"But I was no fool and knew I was most likely a trifle to him. I intended to give him no such conquest. I put that man through his paces and he took it in stride," Jewel wrote. "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 enjoyed Sean and would eventually fall in love."
Penn went on to tie the knot with Robin Wright, but they split in 2010.
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Jewel and her first husband, Ty Murray, dated for a decade before tying the knot in a private ceremony in the Bahamas in 2008. They welcomed their first child in July 2011, three years before they announced their separation.
"Ty and I have always tried to live the most authentic life possible, and we wanted our separation as husband and wife to be nothing less loving than the way we came together," the singer wrote in a blog post.
The "You Were Meant For Me" songstress added, "For some time we have been engaged in private and difficult, but thoughtful and tender undoing of ourselves. Allowing ourselves the time and space to redefine what we are to each other with love rather than with malice."
"I was very slow about going public. We're not people to go out on 'the scene,'" she shared. "Charlie and I are very adventurous, so we travel all over the world together and do a lot of fun things, but it kind of is a luxury just being home and getting to hang out."
The "Down So Long" singer often gushed about the athlete in her interviews until she did not anymore following their quiet breakup.
Jewel reappeared in headlines after she was linked to newly divorced Kevin Costner. Photos of the pair cozying up to each other on Richard Branson's Necker Island in the British Virgin Islands emerged, igniting the buzz.
A source said the relationship between Costner and the "Foolish Games" singer "is fresh but not brand new."
"Jewel likes Kevin's type and Kevin likes to be in a relationship, so this is cool," the source continued. "He is having fun after his contentious divorce. He is glad that is over."
The hearsay started after a separate source said The Guardian star was "warming up to the idea of dating again."