published on in Celeb Gist

Jewel's dating history: Singer, 49, had a thing with Sean Penn and a soap star then was wed to Ty Mu

Jewel had a rich dating history before ‘finding romance’ with Kevin Costner, 68, in the Caribbean in November.

The 49-year-old singer used to be wed to cowboy Ty Murray, which is interesting as Costner is best known for playing a cowboy on the hit series Yellowstone. 

They were man and wife from 2008 until 2014 and have son Kase, 12. 

The country crooner also dated actor Sean Penn, who has been wed to Madonna and Robin Wright, and dated Charlize Theron. And she had a thing with action star Jean-Clade Van Damme, it has been claimed.

Jewel has also gotten close to Charlie Whitehurst, Christopher Douglas and Colin Ferguson.

Here is a look at her love life.

Jewel had a rich dating history before 'finding romance' with Kevin Costner in the Caribbean in November. Here Jewel is seen left and Kevin right

Jewel had a rich dating history before ‘finding romance’ with Kevin Costner in the Caribbean in November. Here Jewel is seen left and Kevin right

In the mid-1990s, she dated actor Sean Penn. 

They met at a concert where Jewel was opening for Peter Gabriel, and soon after, Sean asked her to compose a song for his movie, The Crossing Guard. 

Jewel wrote about their romance in her 2015 memoir, Never Broken. 

Penn is as known for his dating life as he is for his acting career.

He was wed to Madonna from 1985 until 1989, and they romanced each other again several years ago  Sean was then married to Robin Wright from 1996 to 2010 – they have two children: Dylan and Hopper. He then wed Greta Scacchi’s daughter Leila George from 2020 until 2022.

In between he romanced Scarlett Johansson and Charlize Theron.

In the mid-1990s, she dated actor Sean Penn. Seen in 2016 in Nashville

In the mid-1990s, she dated actor Sean Penn. Seen in 2016 in Nashville

In the late 1990s she dated actor Christopher Douglas from Tennessee.

He is now 54 and wed to Darcy Douglas.

The 6ft tall star is best known for roles on the soap operas One Life to Live as Dylan Moody and Passions as Antonio Lopez-Fitzgerald.

In 1994 he appeared in Tori Amos music video for her song Cornflake Girl. 

Douglas worked as a model for major brands, such as Calvin Klein. 

He and Jewel dated for only a few months. 

In the late 1990s she dated actor Christopher Douglas from Tennessee. Seen in 1999 in NYC

In the late 1990s she dated actor Christopher Douglas from Tennessee. Seen in 1999 in NYC

Rumors surfaced in 1997 that she was dating action film star Jean-Claude Van Damme. 

The duo allegedly met at an industry event and dated only for a short while, it was claimed.

They were not photographed together.

He was in the films Bloodsport, Kickboxer, and Universal Soldier. 

The Muscles from Brussels”also had his fair share of high-profile relationships, including marriages to bodybuilder Gladys Portugues and actress Darcy LaPier. 

Rumors surfaced in 1997 that she was dating action film star Jean-Claude Van Damme. The duo allegedly met at an industry event and dated only for a short while, it was claimed

Rumors surfaced in 1997 that she was dating action film star Jean-Claude Van Damme. The duo allegedly met at an industry event and dated only for a short while, it was claimed

In 1999 she met professional rodeo cowboy Ty Murray.

In 2008 they wed and set up house in Texas and welcomed son Kase in 2011.

The two starred on their reality TV show Ty and Jewel: A Rodeo Romance for the Great American Country channel. 

After six years of marriage, the couple announced their amicable split in 2014.

Murray was one of the most accomplished rodeo cowboys in history, with seven All-Around World Championships and two World Bull Riding titles to his name.

He co-founded the Professional Bull Riders (PBR) organization in 1992.

Murray found mainstream TV fame too: he was on Dancing with the Stars and Celebrity Apprentice.

In 1999 she met professional rodeo cowboy Ty Murray. In 2008 they wed and set up house in Texas. Seen in 2011

In 1999 she met professional rodeo cowboy Ty Murray. In 2008 they wed and set up house in Texas. Seen in 2011

She put her arm around her son Kase, 12, in the Caribbean in November

 She put her arm around her son Kase, 12, in the Caribbean in November

In 2015 she dated former NFL quarterback Charlie Whitehurst.

The couple made their first public appearance together at the 2017 Pro Bowl in Honolulu, Hawaii but split later that year.

Whitehurst made a name for himself playing college football for Clemson University before being drafted by the San Diego Chargers in 2006. 

As a seasoned backup quarterback, he had stints with the Seattle Seahawks, Tennessee Titans, and Indianapolis Colts throughout his decade-long NFL career. 

He was known by the nickname Clipboard Jesus for his long hair.

In 2015 she dated former NFL quarterback Charlie Whitehurst. The couple made their first public appearance together at the 2017 Pro Bowl in Honolulu, Hawaii but split later that year. Seen in 2016 in Nashville

In 2015 she dated former NFL quarterback Charlie Whitehurst. The couple made their first public appearance together at the 2017 Pro Bowl in Honolulu, Hawaii but split later that year. Seen in 2016 in Nashville

This comes after she reportedly romanced Kevin during her trip to Richard Branson’s Necker Island in November.

According to a new report from TMZ, they are dating. On Friday photos of them emerged in a very cuddly pose as he had his arm around her waist.

This follows his contentious divorce from Christine Baumgartner this year. 

The two stars were seen sitting very close to each other on Richard Branson’s Necker Island in the British Virgin Islands over the Thanksgiving weekend, as reported by TMZ on Friday.

The Yellowstone star, 68, was on the island for a tennis fundraiser for Jewel’s Inspiring Children Foundation.

It has also been claimed she romanced actor Colin Ferguson, seen here in 2022, but it may just be a rumour

It has also been claimed she romanced actor Colin Ferguson, seen here in 2022, but it may just be a rumour

TMZ claims Costner and the singer flew together to the Caribbean and spent over a week hanging out, were acting ‘flirty,’ and are now dating.

It was also claimed they left the event together after being by each other’s side daily.

The site also shared images with Kevin’s arms around her waist as she spoke into a microphone.

They appeared very flirty and smiled from ear to ear suggesting they really enjoyed each other’s company. 

The site’s source shared: ‘There was definitely something going on. They were flirty, and when they were together, it was like they both just lit up.’

Jewel shared several sizzling images to Instagram during her trip to Branson's Necker Island in November where she got close to Yellowstone star Kevin

Jewel shared several sizzling images to Instagram during her trip to Branson’s Necker Island in November where she got close to Yellowstone star Kevin

Playland: The island held a very exclusive tennis tournament and Kevin even played a game here and there, it was added by PageSix last month

Playland: The island held a very exclusive tennis tournament and Kevin even played a game here and there, it was added by PageSix last month

It was also shared: ‘You could tell they were trying to be discreet, but anybody who saw them could tell something was going on.’

They played double tennis with Sir Richard.

The site’s source also shared that Jewel has been ‘picky about who to date’ but feels Kevin ‘fits the bill,’ meaning she gave him the greenlight for romance. 

Jewel mentioned Costner when talking the fundraising event on her Instagram last week, saying he was ‘kind enough to mentor our kids this year.’

She added of the event: ‘Every year, my foundation and I go to Necker Island to help host a tennis event w Richard Branson to raise funds for our kids. Amazing players like come and support us in playing doubles with the folks who come. 

‘It’s an incredible time, and one I use to relax, rest and play w my son! and Sir Richard was his usual inspiring self- who also plays a mean game of doubles!’

Costner and Jewel were also seen partying with other stars like Emma Watson and Michael Bolton at the private island over the Thanksgiving holiday.

Jewel fits his type: blonde and young. He has also romanced blondes Elle Macpherson, Joan Lunden and Cheryl Teigs, and, of course, his ex wife Christine Baumgartner.

In late November, PageSix reported that Jewel and Kevin were on the same trip together making eyebrows raise. ‘Costner seemed in high spirits and more interested in looking to the future than dwelling on his headline-making split from wife of 19 years, Baumgartner,’ a source told the site.

‘He was talking to other guests about his upcoming movie projects, and he even screened part of his latest movie,’ said an island hopper. His latest film is the two part Horizon: An American Saga which debuts in June 2024. 

Costner also went scuba diving and sailing, the site added. And when he had dinner at night he rubbed elbows with Jewel as well as Emma Watson, Michael Bolton, and tennis stars Genie Bouchard and Mike Bryan.

Guests paid up to $100,000 to visit the island and play with the best tennis stars in the world.

They have kids together: Kevin and Christine seen with their children in 2019

They have kids together: Kevin and Christine seen with their children in 2019 

The good times come after Costner finalized his divorce from his wife of 19 years Christine.

In October Costner and Baumgartner’s very bitter divorce met an end as the two sides settled with the prenup enforced and a massive monetary penalty if it is challenged.

A joint statement from Costner and Baumgartner provided to DailyMail.com read: ‘Kevin and Christine Costner have come to an amicable and mutually agreed upon resolution of all issues pertaining to their divorce proceedings.’

The actor and his wife of nearly 20 years have been embroiled in a months-long legal war which has met a surprise end after a report that Baumgartner had received more than $400,000 to pay the costs of the contentious courtroom battle.

Costner was previously married to Cindy Silva from 1978 to 1994 and they share three children – Annie, 39, Lily, 36, and Joe, 35.

He also shares a son Liam Costner with Bridget Rooney, who he dated after his split with Silva.

Inside Kevin Costner’s colorful love life: Two divorces, a love child and rumors of infidelity

Kevin Costner’s marriage to second wife Christine Baumgartner is coming to an end after 18 years and three children together.

Baumgartner, 49, cited ‘irreconcilable differences’ as the reason for the shock split, which reportedly ‘blindsided’ the Yellowstone star, 68.

And in wake of his latest failed union, DailyMail.com is taking a deep dive into the actor’s colorful love life.

And in wake of his latest failed union to purse designer Christine Baumgartner, DailyMail.com is taking a deep dive into Kevin Costner's colorful love life; seen in 2022

And in wake of his latest failed union to purse designer Christine Baumgartner, DailyMail.com is taking a deep dive into Kevin Costner’s colorful love life; seen in 2022

First wife Cindy Silva

Costner pictured with his first wife Cindy Silva in 1991, she filed for divorce three years later ending their 16 year marriage

Costner pictured with his first wife Cindy Silva in 1991, she filed for divorce three years later ending their 16 year marriage

In November 1994, Costner’s then wife, Cindy Silva, filed for divorce after 16 years of marriage.

‘We have amicably resolved all issues regarding our children and financial affairs and a full marital settlement has been reached. We ask to be allowed the dignity of sorting through this more painful part of our lives in private,’ a statement from the couple read in 1994. 

Costner and Silva met while they were both students at California State University – Fullerton.

They would go on to have three children together.

The pair split amid multiple reports that Costner had been having an affair with a celebrated hula dancer named Michele Amaral while he was filming his multi-million dollar flop Waterworld in Hawaii.

Eventually, Silva was awarded around $80 million in the divorce settlement.

In a 1995 interview, The Bodyguard star took responsibility for his role in the demise of his marriage, but did not go into detail.

‘A series of events conspired to happen at the same time. I know it hurt some people that I had failed in my marriage. And the marriage was my own failure,’ he said.

Costner said in a 1995 interview with Parade Magazine that he never even spoke to Amaral on the phone.

He also listed off the other women he was supposedly linked to including Playboy model Angie Everheart and the daughter of casino magnate Steve Wynn.

‘It was hard on Cindy and our children. It didn’t help things. The only thing it did was hurt. The collapse of my marriage was the hardest thing of all for me,’ the Dances With Wolves star said.

Costner went on to express his love for his first wife: ‘You can put this on the record. Through all the pain, Cindy’s been what I always thought she was a real lady. I still have love for Cindy.’

Silva supported Costner when he was a struggling actor, taking on odd-jobs that included performing as Snow White at Disneyland.

Short-lived fling Bridget Rooney

Shortly after his split from Silva, Costner had a son, Liam, with Pittsburgh Steelers heiress Bridget Rooney

Shortly after his split from Silva, Costner had a son, Liam, with Pittsburgh Steelers heiress Bridget Rooney 

Less than two years after his split from Silva, Costner had a son, Liam, with Bridget Rooney.

She is heiress to the Pittsburgh Steelers, and the aunt of actresses Rooney and Kate Mara.

In 1996 Rooney insisted that she was ‘110% sure who the father’ of her child was. 

But Rooney still ‘insisted on a paternity test’ to prove paternity, according to a 2002 article from PEOPLE.

That months-long affair is rumored to have cost the actor $7 million.

Liam in now 27-years-old.

‘Mistress’ Michele Amaral 

In 1994, Kevin Costner was widely reported to have had an affair with hula dancer Michele Amaral while filming Waterworld

In 1994, Kevin Costner was widely reported to have had an affair with hula dancer Michele Amaral while filming Waterworld

Costner allegedly had an affair with a celebrated hula dancer named Michele Amaral while he was filming his multi-million dollar flop Waterworld in Hawaii. 

Amaral was also married as well as being a mother-of-two when she met Costner.

A report at the time in the New York Daily News said that the pair met at the Mauna Lani hotel and shortly afterwards Amaral was ‘spotted creeping out of his $4,500-a-day villa.

According to a Departures Magazine feature, Amaral has taught hula across the world and is known as the island’s premier soloist.

The Daily News report said that Silva was alerted to the affair by someone who was working on Waterworld and was fired.

The same article accused Costner of multiple infidelities during his marriage.

At the time Costner strenuously denied the allegations saying that he was merely interviewing Amaral for a job.

During an interview where Amaral was brought up, Costner became infuriated.

‘This woman has done nothing wrong and yet has had to share the harsh light of celebrity with me. I feel embarrassed, and I don’t think there’s one thing I can do to make her life better.’

‘This woman has a name and to make her a thing is the worst part of all. It’s wrong for her and her husband,’ Costner said.

Second wife Christine Baumgartner 

Costner and second wife Baumgartner first began dating in 1998, having met around 1996 while Costner was filming his movie Tin Cup. They wed in 2004; seen in 2022

Costner and second wife Baumgartner first began dating in 1998, having met around 1996 while Costner was filming his movie Tin Cup. They wed in 2004; seen in 2022 

Costner and second wife Baumgartner first began dating in 1998, having met around 1996 while Costner was filming his movie Tin Cup.

The Bodyguard star said that at the time he first met her, he wasn’t ready to fall in love again. 

Both are graduates of California State University – Fullerton. Baumgartner graduated with a degree in business. 

They married in 2004 in Aspen, Colorado, where Costner has long maintained a 160-acre ranch, known as The Dunbar. Rooms can be rented on the property for as much as $36,000 per night.

The reason for the long courtship was because Costner was not sure if wanted more kids. The uncertainty even led them to break up for a period prior to their engagement.

‘Fear kept me from marrying Christine. [She] wanted a child, but I was afraid I couldn’t be an effective father.’

‘I woke up and thought, ‘Am I going to lose a beautiful woman who is willing to be with me to my very last breath because I am afraid to say yes to a child?’ That’s all it took. Sometimes you learn the thing you’re most afraid of will save your life,’ he told Closer Weekly in 2018.

Costner told the Daily Telegraph in 2011 that the reason for his four year hiatus from making movies was because of his new family.

As a recently as 2020, Costner spoke glowingly about how the couple’s relationship strengthened during the Covid-19 pandemic. He told People: ‘Our partnership has really come into focus about what we do for each other and how we deal with our family.’

The couple share three children, Grace, 12, Hayes, 14, and Cayden, 15, and both have filed for joint custody; seen in 2019

The couple share three children, Grace, 12, Hayes, 14, and Cayden, 15, and both have filed for joint custody; seen in 2019

In 2022, Radar Online reported that Costner was given an ultimatum from his wife. The report said that she was demanding that he quit his hit show Yellowstone due to the fact that he was gone from home so often.

‘The show is such a mega-hit, producers want it to go on forever! [Baumgartner] wants a firm commitment this is his last season — or he might have to!,’ a source told the website.

And on Tuesday, May 2, it was revealed that Baumgartner had filed for divorce after 18 years of marriage.

A representative for the Yellowstone star asked for privacy  while saying that ‘circumstances beyond his control have transpired which have resulted in Mr. Costner having to participate in a dissolution of marriage action’ with Baumgartner.

The couple share three children, 12, 14 and 15, and both have filed for joint custody.

The family’s primary residence was in Ventura, California, 30 miles south of Santa Barbara, where they also own an oceanfront mansion.

The couple settled with prenup enforced in September 2023. 

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