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Dierks Bentley and Cassidy Black | Dierks Bentley, Cassidy Black, Jordan Catherine Bentley, Evalyn Day Bentley and Knox Bentley | Source: Getty Images | Instagram.com/dierksbentley
Dierks Bentley and Cassidy Black | Dierks Bentley, Cassidy Black, Jordan Catherine Bentley, Evalyn Day Bentley and Knox Bentley | Source: Getty Images | Instagram.com/dierksbentley

Dierks Bentley & His Wife's Love Story Goes Back to Childhood When He 'Wasn't Cool Enough' to Date Her

Olawale Ogunjimi
Sep 11, 2022
11:00 P.M.

Dierks Bentley and his wife, Cassidy Black, have been married for 17 years and share three children. But there was once a time when the country music singer felt he was not cool enough to approach or date his beautiful partner. Inside their inspiring love story.

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Since American Country Music Singer and Songwriter Dierks Bentley topped the music charts in 2003, fans have followed his life. But apart from enjoying his impressive albums, the entertainment icon's fans also take inspiration from his love life.

The singer has been married to his beautiful wife, Cassidy Black, for almost two decades, but their love story dates back to childhood.

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Bentley and Black first crossed paths in the eighth grade at Ingleside Middle School, Phoenix. But the singer recalled not being confident in himself enough to approach Black, despite having a huge crush on her. In his words:

"I had a crush on her the whole time, but I wasn't cool enough. I was too immature and into drinking beer and blowing things up."

Dierks Bentley and Cassidy Black attend the 55th annual Country Music Association awards at the Bridgestone Arena on November 10, 2021 in Nashville, Tennessee. | Source: Getty Images

Dierks Bentley and Cassidy Black attend the 55th annual Country Music Association awards at the Bridgestone Arena on November 10, 2021 in Nashville, Tennessee. | Source: Getty Images

Nevertheless, it was only a matter before the pair started dating. They eventually became romantically involved in high school after each went out with the other's best friend.

However, Bentley and Black would have to enjoy their romance from a long distance. At 19, the country music singer moved to Nashville to pursue his dreams while Black worked in an advertising firm in San Francisco.

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Dierks Bentley and Cassidy Black attend the Universal Music Group 2015 Post GRAMMY Party at The Theatre Ace Hotel Downtown LA on February 8, 2015, in Los Angeles, California. | Source: Getty Images

Dierks Bentley and Cassidy Black attend the Universal Music Group 2015 Post GRAMMY Party at The Theatre Ace Hotel Downtown LA on February 8, 2015, in Los Angeles, California. | Source: Getty Images

But despite being miles apart, the couple did everything possible to keep their love for each other alive. Here are more details about Bentley and Black's inspiring love story.

Bentley and Black's Love Story

During their time far away from each other, Bentley and Black still kept in touch. The "Gonna Get There Someday" confessed to People that he would frequently send his girlfriend love letters. According to the singing icon:

"I used to write her all these crazy love letters that I'd FedExed out to her!"

Dierks Bentley and Cassidy Bentley arrive at the 44th annual Academy Of Country Music Awards held at the MGM Grand on April 5, 2009, in Las Vegas, Nevada. | Source: Getty Images

Dierks Bentley and Cassidy Bentley arrive at the 44th annual Academy Of Country Music Awards held at the MGM Grand on April 5, 2009, in Las Vegas, Nevada. | Source: Getty Images

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The letter writing continued for some time, but the long distance threatened their relationship at some point. At the time, Bentley had reached a commendable level of success in his career, touring with Kenny Chesney, and almost gave up on Black.

However, despite the circumstances surrounding their move, Bentley said he was using every available opportunity to bond with his wife and children.

The singer told People he did not think he could make Black happy because his life was crazy. However, all he would need to have a change of heart was to see his childhood love. On February 4, 2005, Black flew from San Francisco to Las Vegas for Bentley's show, where they would eventually reunite.

Dierks Bentley and Cassidy Black arrive at the 47th Annual Academy Of Country Music Awards held at the MGM Grand Garden Arena on April 1, 2012, in Las Vegas, Nevada. | Source: Getty Images

Dierks Bentley and Cassidy Black arrive at the 47th Annual Academy Of Country Music Awards held at the MGM Grand Garden Arena on April 1, 2012, in Las Vegas, Nevada. | Source: Getty Images

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Upon seeing each other, Black and Bentley had a mutual love feeling, and the spark they once had reignited. After the show, Black returned to San Francisco, but Bentley ensured she remained there only for a short time.

He purchased a three-story, 2,100 square feet contemporary home in Hillsboro village, and in no time, Black quit her job in San Francisco and moved in with her man. Ten months later, the music guru took their relationship to the next level.

Dierks Bentley and Cassidy Black attend the 2008 CMT Music Awards at Curb Event Center at Belmont University on April 14, 2008, in Nashville, Tennessee. | Source: Getty Images

Dierks Bentley and Cassidy Black attend the 2008 CMT Music Awards at Curb Event Center at Belmont University on April 14, 2008, in Nashville, Tennessee. | Source: Getty Images

In December 2005, Bentley popped the big question during a tour date in Las Vegas. The following day, the couple eloped to Mexico and tied the knot in a little chapel. Black recalled that the occasion was beautiful, private, and authentic.

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Inside Bentley's Happy Life with His Beautiful Family

Bentley reached another great milestone in his career two weeks after their wedding. He earned his second No.1 single, "Come a Little Closer," and the entertainment star could not have been more thankful that some success came later in life.

Dierks Bentley and his wife attend the 44th Annual CMA Awards at the Bridgestone Arena on November 10, 2010, in Nashville, Tennessee. | Source: Getty Images

Dierks Bentley and his wife attend the 44th Annual CMA Awards at the Bridgestone Arena on November 10, 2010, in Nashville, Tennessee. | Source: Getty Images

He credited his wife for his success, noting that it was one of the moments he was most grateful for Black. According to Bentley:

"It's so nice to share a lot of ups, a lot of downs, a lot of in-between moments with her. It's been a crazy, crazy ride, but certainly right now, for this to be happening is awesome."

Several years later, Bentley's career is still thriving, his marriage is as strong as ever, and he and Black are doting parents to three children, Evie, 12, Jordan, 10, and Knox, 7. Now, the family of five live happily in Colorado.

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During a 2020 interview, the singer stated that he had taken his family for Spring break in March that year, but they never left due to the coronavirus pandemic and restrictions. In his words:

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"I went there with my family for Spring Break in March and never left. I put my kids in school out there, and we just moved."

However, despite the circumstances surrounding their move, Bentley said he was using every available opportunity to bond with his wife and children.

Dierks Bentley and his daughter arrive at the 2018 CMT Artists of the Year at Schermerhorn Symphony Center on October 17, 2018, in Nashville, Tennessee. | Source: Getty Images

Dierks Bentley and his daughter arrive at the 2018 CMT Artists of the Year at Schermerhorn Symphony Center on October 17, 2018, in Nashville, Tennessee. | Source: Getty Images

According to the starlet, he made up for lost time with his family. After spending about 18 years touring and being absent from home every weekend, he was happy to do things like ride bikes with his kids to school.

Pictures splattered all over Bentley's social media prove that the singer is now dedicated to spending time with his family. In June 2020, the proud dad shared a video of him and his daughter, Evie, flaunting their musical talents.

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The clip showed the pretty girl singing into a microphone while her dad sang along and played the acoustic guitar. Bentley added the caption:

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"Working on my acoustic/sideman chops."

In another post, the father of three was photographed posing with one of his sons and three dogs in a picturesque environment. Then, in May 2022, he shared a beautiful picture of himself and his family having a good time in the Bahamas. The family of five looked relaxed and happy while wearing big smiles.

Overall, Bentley feels blessed to have his beautiful wife and children at his side. Even though he still pursues his singing career, the singer's family will always be one of his topmost priorities.

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