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KEITH URBAN & NIKI TAYLOR
The country star has had his share of lovely ladies: Four years before marrying Oscar winner Nicole Kidman in 2006, he dated supermodel Taylor, seriously enough that they got matching amor vincit omnia (Latin for "love conquers all") tattoos. Not surprisingly, both had them covered up once the relationship soured.
JEWEL & SEAN PENN
During a mid-'90s separation from then-girlfriend Robin Wright, the actor hooked up with this country cutie and later directed her hit video "You Were Meant for Me." But he apparently wasn't meant for her: Penn married Wright in 1996 (they divorced in 2010) and Jewel went on to date Antonio Sabàto Jr. before settling down with pro rodeo cowboy Ty Murray in 2008.
DWIGHT YOAKAM & SHARON STONE
The "Honky Tonk Man" has squired several famous women – Bridget Fonda and Karen Duffy among them – but his most memorable ex is Stone, whom he met while shooting a 1992 Ebel watch ad. But things didn't end prettily: After they parted ways, she famously compared kissing him to eating "a dirt sandwich."
TAYLOR SWIFT & JOHN MAYER
At the very least, the duo's brief 2009 romance produced some really interesting music. After their breakup, a then-19-year-old Swift did what she does best: wrote a revenge song, the salacious "Dear John." In 2013, Mayer sought his own revenge with "Paper Doll," which referenced the number 22 (Swift's hit song) and a scarf (which Swift mentioned in her "All Too Well"). Burn!
KENNY CHESNEY & RENéE ZELLWEGER
Sporting a Carolina Herrera gown, the Bridget Jones star said to the singer on the island of St. John in May 2005. They'd met just four months before at the Concert of Hope tsunami relief benefit, and it took about the same amount of time – four months – for Zellweger to file for an annulment and raise more than a few eyebrows by citing "fraud" as the reason for their split.
LYLE LOVETT & JULIA ROBERTS
She had high-profile romances with Jason Patric, Kiefer Sutherland and Benjamin Bratt before marrying cameraman Danny Moder in 2002, but few remember that Roberts was once wed to big-haired singer Lovett. After a reported three-month courtship, the two – who'd appeared together in 1992's The Player – exchanged vows in June 1993 in Marion, Ind., while he was on tour but went their separate ways just 21 months later.
CARRIE UNDERWOOD & CHACE CRAWFORD
The TV hunk and his singing sweetheart had a very Gossip Girl-esque breakup in April 2008: They did it by text. "It was completely mutual," Underwood, who began seeing Crawford in fall 2007, told Extra. "It's like, 'Peace out.'" Crawford wasn't quite so dismissive; his sister Candice told PEOPLE, "He was upset about the breakup. It's always hard when you lose a relationship."
TANYA TUCKER & DON JOHNSON
The "Delta Dawn" singer has never been married but counts Merle Haggard, Glen Campbell and Andy Gibb as former lovers, as well as Don Johnson, with whom she canoodled after working together on the 1979 TV movies Amateur Night at the Dixie Bar and Grill and The Rebels. But that all ended in 1981, when Johnson reportedly ditched Tucker at an L.A. restaurant after meeting actress Patti D'Arbanville and spending the night with her.
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