Inside Kevin Costner's Relationship History

Although he's now best known for playing the grizzled patriarch John Dutton in "Yellowstone," Kevin Costner was once regarded as one of the biggest hunks in the biz. His sizzling chemistry with the late Whitney Houston in 1992's "The Bodyguard" cemented his status as a Hollywood heartthrob, as well as a commercially bankable star. For many years, he was also one of the industry's most eligible bachelors, having lived the single life and flitted between various paramours before finally settling down in the mid 2000s. He's even rumored to have dated the likes of Halle Berry, Courteney Cox, and model turned erstwhile French first lady Carla Bruni (though these alleged trysts are uncorroborated).

Despite his myriad dalliances over the past three decades, Costner has opted to remain tight-lipped when it comes to his love life. However, chatting with Parade in 2012, he rather surprisingly discussed his private life and, specifically, what he feels makes a relationship work. "Maybe it's the ability to say you're sorry," he reflected. "I know that sounds so simple. If you're willing to tell somebody that you love them, are you also willing to say you're sorry? You need to, even when you think you're in the right."

As his increasingly complicated divorce from Christine Baumgartner generates intrigue (not to mention headlines), let's take a trip down memory lane and find out which women have stolen "The Bodyguard's" heart throughout the years. Here's a look inside Kevin Costner's relationship history.

Kevin Costner first met his college sweetheart, Cindy Silva, in 1975. According to pals, the smitten bachelor only had eyes for Silva, who was working as a Snow White impersonator at Disneyland. "(Kevin) was a skinny little runt, just over six feet and weighed about 150 pounds," his college pal Craig Cessna told the Los Angeles Times. "We were all pretty geeky. He had dates–but he was crazy about 'Snow White.'"

The couple tied the knot three years later and Silva supported her husband's efforts to become an actor. They welcomed three children together: Annie, born in 1984, followed by Lily in 1986, and their son, Joe, born two years later. Despite being married to a Hollywood A-lister, Silva opted to remain out of the limelight, with Costner's brother telling Time that she had no desire to be a Tinseltown trophy wife. In 1989, the actor waxed lyrical about Silva in an interview with People. "She was beautiful, she was sweet, she was smarter than me ... she represented everything about women that I like," he reflected. However, he also alluded to troubles within their relationship, confessing that he found marriage hard at the best of times.

In 1994, the couple called it quits after Costner was accused of having affairs with two women, British nightclub receptionist Sheri Stewart and Michelle Amaral, who worked at the hotel Costner was staying at during the filming of "Waterworld." Silva reportedly received an eye-watering divorce settlement of $80 million.

In the early days of his career, Kevin Costner was known as a devoted family man. But following his separation from Cindy Silva, he began developing a reputation as a womanizer. The actor himself had previously alluded to his wandering eye, conceding that he doesn't have a type and finds all women attractive. The year he divorced Silva, he made the movie "Wyatt Earp," where, as noted in People, he apparently flirted with a production assistant. Another woman then alleged that he touched her inappropriately during a seemingly innocuous limo ride.

This bad boy rep continued, and he reportedly had a rendezvous with model/actor turned real estate entrepreneur Peggy Trentini shortly after his separation. In 2011, Trentini published her book, "Once Upon a Star," in which she dished about her alleged dalliance with the "Yellowstone" actor.

Chatting to Radar, she claimed that she and Costner never had a serious relationship, apparently due to his notoriety as a ladies' man. "Kevin would have his friends bring girls to his house so he could meet as many as possible to find a hot girlfriend," she claimed. "He was so fun and flirty but I never took him seriously because my friends all told me he was a huge womanizer." But Trentini, who also allegedly had romantic encounters with Johnny Depp and Billy Idol, conceded that she wasn't dating Hollywood stars in the pursuit of long-term relationships; she was just having fun.

Remaining true to his womanizer public image, Kevin Costner swiftly welcomed more children. In 1996, he had a tryst with Bridget Rooney, niece of Pittsburgh Steelers owner Dan Rooney. She soon fell pregnant.

At the time, New York Magazine noted that Costner was often spotted at Pittsburgh Steelers games, intimating that he was the father. "I'm 110 percent sure who the father is," Bridget told the magazine. "I'm just enjoying my pregnancy." The outlet reported that Costner wasn't entirely thrilled at the prospect of welcoming another child. But Bridget said that she was more than happy to raise her child as a lone parent. "There was only one way to go with this," she explained. "I'm 34 years old, and I'm fortunate to have a baby. I didn't even think of the A word, only the B word." In 1996, Bridget gave birth to her son, Liam. At first, Costner was reportedly unwilling to acknowledge paternity. Eventually, however, he took a DNA test, which confirmed that he is indeed the father. An unnamed source told People that Costner rarely saw his son, but he set up a trust fund for him to secure his future. Curiously, when Parade asked Costner about his adult children he made no mention of Liam. 

Bridget Rooney moved on from her fleeting fling with Costner and wed billionaire businessman Bill Koch in 2005. Both Bridget and her son keep out of the limelight, and it appears that Liam now works a regular job in real estate.

For three years, Kevin Costner dated British socialite Birgit Cunningham. In the mid '90s, Cunningham left London for Los Angeles and it was there that she met the actor. Chatting to the Evening Standard, she revealed that the pair had an open relationship.

In 2006, she defended Costner when he was accused of acting inappropriately towards a masseuse. Speaking to Digital Spy, she said the star was a perfect gentleman throughout their romance. "Kevin is very romantic and tender, he would never do anything so vulgar," she argued. "He would be more interested in a long, loving kiss rather than the naughty bit. He really is Mr. Perfect, squeaky clean, if a little naïve when it comes to realizing the effect he has on girls."

While Costner was involved in public scandals years earlier, Cunningham was embroiled in two of her own. In 2002, she was involved in a paternity suit with racing driver Harry Nuttall. She told the Evening Standard that Costner, with whom she had remained friends, comforted her amid the public fallout. Then, in 2011, she admitted to an extramarital tryst with Conservative politician Thomas Strathclyde. Writing for The Telegraph, she said that the British tabloids used her past relationship with Costner as fuel in demonizing her. "There was one per cent interest in the child maintenance issue," she wrote, "and 99 per cent interest in my pink bikini, my rather colorful life in LA and the fact that I had dated Kevin Costner."

In 1995, Kevin Costner was linked to Angie Everhart, who was a popular model of the era and one of the first redheads to break into the fashion mainstream. At the time, New York Daily News claimed that Costner was in the midst of attempting to reconcile with Cindy Silva, to no avail. He then reportedly took a liking to Everhart after spotting her photo in a magazine, and allegedly performed a number of romantic gestures to steal her heart (including supposedly hiring a private plane filled with flowers to whisk her away to him).

The pair were supposedly spotted getting cozy on a dinner date before embarking on a getaway in Santa Barbara. However, this was apparently their one and only encounter. That year, Everhart appeared on "Late Night with Conan O'Brien" to address the rumors, and subsequently refuted the claim that Costner hired a rose-decked jet to fly her to their date. "I met him in a restaurant in California," she explained, "and I walked out, they took pictures of me and 'Hard Copy' put me on, saying that I was the next Mrs. Costner, and it's just a total, blatant lie." She joked that she probably would have fallen for Costner if he had indeed hired a private plane to woo her.

Interestingly, New York Daily News notes that Everhart previously dated Jimmy Traboulsi, an ex of fellow model Elle MacPherson, whom Costner would also go on to date (but more on her later).

The mid '90s were seemingly a busy time for Kevin Costner. After dating models and socialites, he moved onto journalist Joan Lunden. She dated the Hollywood star in 1996, towards the end of her nearly 20-year tenure as host of "Good Morning America." 

While Angie Everhart said that tales of Costner's grandiose romantic gestures were media fabrications, Lunden revealed that the actor did indeed woo her in a manner straight out of a '90s romcom. "He got this yacht and we sailed around New York Harbor and had dinner," she told TV Guide (via the Orlando Sentinel). "It was quite romantic and quite beautiful. When he first walked on the boat and smiled at me as only he can smile and said, 'Boy, I've waited so long to meet you,' I almost fell over."

Although Lunden was totally smitten with the "Waterworld" star and his old school swooning techniques, it was not to be. The relationship was merely fleeting, with the journalist blaming intense media intrusion (the tabloid magazine Star claimed that Lunden called things off with her Hollywood beau for a younger lover) and Costner's hectic work schedule. "All the press made me very self-protective in subsequent dating," she conceded in her chat with TV Guide. There are even claims that Lunden, who argues that she was fired because "GMA" execs wanted to replace her with a younger woman, fell out of public favor due to her dalliance with the A-lister.

Elle MacPherson was one of the biggest supermodels of the '90s. At the height of her it-girl heyday in 1996, she was linked to Kevin Costner. The pair reportedly met after the model attended a party hosted by Costner; as is the actor's MO, he apparently treated MacPherson to a romantic serenade. It's also possible that they met through Fashion Café founder Tommaso Buti, who was friends with both Costner and MacPherson. At the time, the Mirror quoted the actor as saying that he went a little overboard with embracing the bachelor lifestyle following his divorce from Cindy Silva, but had finally found a woman he wanted to settle down with. "I have met a lot of wonderful ladies since I became single, but today I have reached a very happy phase in my life," he apparently declared. "I feel I have met my equal with this beautiful, talented, funny and lovely person. Her name is Elle."

Pals who chatted to the outlet claimed that things were getting serious between the two, and MacPherson had begun befriending Costner's children. "He's attracted to her physically and had admired her from a distance for some time before finally dating her," a friend said. "They have come together at the perfect time in their lives."

It's unclear how long the couple remained together, but they were photographed looking cozy at one of Diddy's parties in 1998. A Baltimore Sun profile from the following year stated that Costner was once again single.

Around the time he was dating Elle MacPherson, Kevin Costner was also linked to Tawny Little. Although Little is best known as a TV host, she was also famed for being crowned Miss America 1976, continuing Costner's tradition of having eyes for the most admired beauties in the nation. She and Costner were rumored to be dating circa 1997, when they were spotted on a succession of dates. In another instance of Costner love life overlap, Little had previously been linked to Sylvester Stallone, who also dated fellow alleged Costner ex Angie Everhart.

According to insiders who chatted to Scotland's the Sunday Mail, the attractive twosome enjoyed rather charming dates. "Their first real date was when Kevin took her to singer Patti LaBelle's Hollywood Bowl concert. Tawny was thrilled," a source dished. "She fried chicken and packed a picnic for them. She even got a strawberry pie from that same little restaurant."

Again, this appears to have been a fleeting dalliance. In a Los Angeles Times profile from 1998, Little expressed her dismay at being thrust in the limelight following her romance with the A-lister. "This is going to sound ingenuous," she said, "but I didn't really set out to be famous and live in that kind of limelight ... It was exciting, of course, but it obviously caused me a lot of pain in my life ... Public, tabloid romances are no fun. Not what anyone would want."

A decade after divorcing Cindy Silva and casually dating numerous celebs, a 49-year-old Kevin Costner tied the knot with handbag designer Christine Baumgartner, then 30, in 2004. It was an epic affair (we wouldn't expect anything less from the serenade-loving ladies' man), with Baumgartner arriving at the wedding in a horse-drawn carriage. Although Costner put a ring on it in the aughts, he actually met Baumgartner in the mid '90s, before reconciling in 1998. "We exchanged numbers, and I told her ... did she mind if I called her in two weeks," Costner told People. "I did not realize that was like an insult to a woman."

In his sit-down with Parade, Costner revealed that Baumgartner desperately wanted kids, but he wasn't so sure about adding to his brood. "She said ... 'When you come to your senses, come back to me.' And I did," he divulged. Baumgartner and Costner welcomed three kids: Cayden in 2007, Hayes in 2009, and daughter Grace in 2010. In 2019, Costner admitted to the Mirror that he was anxious about his much younger wife losing interest in him. "I try to take care of myself," he said. "I have a beautiful wife and I don't want her to look anywhere else."

After 18 years of marriage, Baumgartner filed for divorce in May 2023. Costner and Baumgartner's divorce drama was highly publicized, with the latter requesting $248,000 a month in child support and reportedly refusing to leave the family home. In September, the divorce was settled privately.

Following his divorce from Christine Baumgartner, Kevin Costner was said to be linked to Reese Witherspoon in November 2023. The claims of Hollywood's supposed newest power couple spread like wildfire, but Witherspoon's rep swiftly dismissed the rumors as little more than online tattle. Soon enough, however, Costner reportedly found love again. 

In December, there were claims that he had begun romancing multi platinum-selling songstress Jewel. Onlookers told InTouch Weekly that he took a liking to Jewel while attending a charity event on the British Virgin Islands, and they immediately hit it off. The pair were spotted getting super close, with Costner (ever the gent) swooping in to cuddle his supposed lady love as she made a speech for the Inspiring Children Foundation, which she founded. 

According to insiders who chatted to TMZ, the twosome flew to the event together and subsequently enjoyed a romantic Caribbean getaway. "There was definitely something going on," a source dished. "They were flirty, and when they were together, it was like they both just lit up." Another eyewitness claimed that the duo were trying their best to act coy and hide their apparent steamy rapport. "But anybody who saw them could tell something was going on," they said. Insiders also noted that Costner was just the kind of man Jewel has apparently been on the lookout for. Although neither party has yet to confirm the relationship, Jewel took to Instagram to pay tribute to her rumored beau, whom she thanked for his contributions to her charitable foundation.