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Kenny Chesney dating history: Who has the country icon dated?

Kenny Chesney dating history: Who has the country icon dated?

KENNY Chesney has become one of the biggest stars in country music, topping the charts for over three decades.

The country music legend has managed to keep most of his dating life out of the public eye, leaving fans wondering whether he has a special someone in his life right now.

AP:Associated PressCaroline Herrera snapped a photo of Kenny Chesney kissing Renée Zellweger, wearing her Carolina Herrera wedding dress, on the beach in St. John on May 9, 2005[/caption]

Has Kenny Chesney ever married?

Kenny Chesney has tied the knot before, though the marriage didn’t last long.

On May 9, 2005, Chesney married American actress Renée Zellweger.

Zellweger rose to prominence starring alongside Tom Cruise and Cuba Gooding Jr. in the 1996 movie Jerry Maguire.

She also gained fame for portraying the titular character in the romantic comedy Bridget Jones’s Diary.

She has won two Academy Awards, four Golden Globe Awards, and two British Academy Film Awards.

Chesney and Zellweger met in January 2005 at a charity event for the 2004 Indian Ocean earthquake and tsunami.

The duo married in a romantic ceremony on the island of St. John, one of the Virgin Islands in the Caribbean Sea.

Just four months later in September 2005, Chesney and Zellweger announced that they were getting an annulment.

Zellweger cited fraud as the reason for the annulment.

In an interview with Oprah Winfrey, Chesney tried to explain why his marriage failed, saying: “I panicked.”

Chesney also said that marriage is “tough…it really is tough. And [Zellweger is] a sweet soul, no doubt about it, but I just wasn’t ready.”

Chesney also spoke to Anderson Cooper about his failed marriage.

In a 2007 episode of 60 Minutes, he said: “The only fraud that was committed was me thinking that I knew what it was like… that I really understood what it was like to be married, and I really didn’t.”

The annulment was finalized in December 2005.

Neither Zellweger nor Chesney have remarried, though Zellweger recently got engaged in 2023.

Who has Kenny Chesney dated?

Not much is known about Chesney’s dating life before his marriage to Zellweger.

After the two split, he met Amy Colley, a burn-unit nurse and pageant queen.

Colley was named Miss Tennessee in 2005.

The two vacationed together in Malibu and the Bahamas, and even spent Thanksgiving together with each other’s families.

The relationship ended after about two years, when Chesney was spotted with another woman, Jenn Brown, in Cancun, Mexico.

Brown was a former Division One college athlete before becoming a sports broadcaster for ESPN.

She made history after becoming the first female correspondent of Inside The NFL.

In a 2009 interview with Playboy magazine, Chesney claims to have slept with “over 100” women.

He said: “There were years when I had a better summer than A-Rod,” referencing former professional baseball player and self-proclaimed womanizer Alex Rodriguez.

He added: “My first five years on the road were intense because I was the guy in college who never got laid until I started playing guitar.”

In the same interview, Chesney explains that he’s not cut out for a normal life: “I have friends who have a normal family, kids, and a dog, and I think I would blow my brains out.”

However, nearly fifteen years later, Chesney appears to have somewhat settled down into domestic bliss.

Though he hasn’t remarried, he’s been with his longtime partner, Mary Nolan, for over a decade.

GettyKenny Chesney and Mary Nolan attend the 2014 American Country Countdown Awards at Music City Center on December 15, in Nashville, Tennessee[/caption]

The childless couple also shared two rescue dogs, Poncho and Ruby.

Chesney met Nolan in 2012, and though little is known about their relationship, they reportedly met at one of his concerts.

They were pictured together at the 2014 American Country Countdown Awards and the 2016 Country Music Association Awards.

Some media outlets reported that the couple got engaged – and even tied the knot – in 2022, however, neither Chesney nor Nolan have confirmed any rumors.

Does Kenny Chesney have kids?

Kenny Chesney does not have any children.

His only sibling, half-sister Jennifer Chandler, also doesn’t have kids.

Chesney seems to be enjoying life without kids of his own, but is happy to take on the role of “uncle” to his friends’ children.

In a December 2020 post on Instagram, American country singer Jake Owen shared a snap of his daughter and the country music star hugging and smiling for the camera.

He captioned the post, “Pearl and her Uncle Kenny.”

Owen is famous for his hits Barefoot Blue Jean Night, Down To The Honkytonk, and Best Thing Since Backroads.

He’s opened for Chesney multiple times on tour.

The duo first performed together during Chesney’s Road and Radio tour in 2006.

Chesney is also a “dad” to his pets.

A lifelong animal lover, he helped rescue nearly 1,400 animals after Hurricane Irma.

Chesney also recently shared the tragic loss of his rescue dog, Ruby.

On December 4, 2022, Chesney posted a photo of Ruby and wrote a sweet tribute in the caption: “Today we lost Da Ruba Girl.”

Ruby was the inspiration behind Chesney’s hit song, Da Ruba Girl.

“Ruby lived her life never holding anything against anybody. She had an ancient, calming soul. She was honest and authentic, she was a protector, she took a warrior’s path in the journey of her life.”

He also referred to his other dog, Poncho, in the tribute: “I know she is happy to have had Poncho in her life. They were partners in crime and never spent a day apart.”

Chesney adopted Poncho, a Goldendoodle, in 2012.

The country icon, who stays nearly silent about his love life, also name-dropped long-time partner Mary Nolan in the post.

He credited his girlfriend for adopting Ruby: “But [Ruby] is forever grateful that Mary saved her from the shelter. But really they ended up saving each other.”

The singer added: “We loved you and thank you for teaching us how to love unconditionally. You were one heaven of a dog.”

On July 16, Chesney shared another snap on his Instagram, this time spreading Ruby’s ashes in the ocean.

He captioned the post: “Spreading Ruby’s love on the West Coast.”

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