June 29

Dierks Bentley and wife Cassidy Black’s Long Winding Road to Love

Dierks Bentley and wife Cassidy Black have been married for 15 years now, but the road before they said “Yes, I do” was a long and winding one. The couple met way back in middle school and then started an on-and-off relationship. But once they finally realized that they were each other’s soulmates, everything just clicked into the right place and the right time.

So, let’s take a look back at their journey from the day they met to their struggles as a couple to the day that changed their lives forever. 

First Chapter: ‘Right place, wrong time’

Dierks Bentley met his future wife, Cassidy Black, at Ingleside Middle School in Phoenix, Arizona. The two attended eighth grade together, and according to one interview with Bentley, he confessed that he felt he wasn’t cool enough for Black back then. He was immature and very much loved getting into trouble, like drinking beer and blowing things up. 

When they started high school, the two remained within each other’s orbit. Bentley actually dated Black’s best friend (and Black reportedly dated his best friend as well), but things didn’t work out well between them, and they had to end the relationship. Eventually, Bentley and Black ended up together and started dating. 

Bentley decided to pursue country music at the age of 19 and move to Nashville. On the other hand, Black went across the country to San Francisco, where she got a job at an advertising firm. They had an on-and-off relationship, and the couple often questioned whether they were right for each other. Throughout the relationship, they experienced a lot of ‘right place, wrong time’ setbacks. 

But Bentley was still definitely smitten with her, sending Black what he called in retrospect ‘over the top’ love letters. (Black definitely kept those letters as she jokingly said she could sell them on eBay.) Then in 2005, Bentley successfully made a name in the industry and found himself opening for Kenny Chesney and George Strait

And it was during one of these tours that they finally knew that they were really for each other. No doubts. 

Black showed up at George Strait’s Las Vegas concert, where Bentley opened up for her. When he saw her walking towards his tour bus, he just knew. As for Black, she confessed that she had a weird feeling right when he saw him, and she cried when she said goodbye. 

Shortly after, in December of 2005, the couple got engaged. And Bentley wasted no time at all and asked Black to elope with him to Mexico the next day. And he already picked out her wedding dress. So Dierks Bentley and Cassidy Black exchanged vows in a beautiful and private ceremony in a little chapel in Mexico. 

Who Is Dierks Bentley’s wife, Cassidy Black?

Just like any country music singer, Dierks Bentley drew a lot of inspiration for his songs from real-life experiences and the people around him. And two of the Dierks Bentley songs that became hits – “Woman, Amen” and “Black” – were both inspired by the love of his life, Cassidy Black. 

Cassidy Black was born on September 6, 1975. There was no information about her family and her childhood except that she attended Ingleside Middle School along with her now-husband, Dierks Bentley. And she decided to keep things private even after being married to the world-famous country star. She doesn’t have any public social media platforms, although a lot of fans loved to see more of her. 

Although she is very private, Black never failed to support Bentley, and she has been by his side in numerous Red Carpet appearances. She also appeared in the music video of “Black,” a song named after her, where they shot in the chilly Black Sand Beach in Iceland. She is also known as a professional charity runner. Her first marathon was the 2014 Boston Marathon, and three years later, she joined again and finished it within 3 hours and 26 minutes. 

Aside from that, she also co-owns a chain of salons in Nashville named The Dry House.

Second Chapter: Meet Dierks Bentley’s Children

The couple was blessed with three lovely kids – Evelyn Day, Jordan Catherine, and Knox. And they’re definitely proud parents. 

Evelyn Day, their oldest daughter, was born on October 4, 2008. She is now 12 years old, and it looks like she definitely got the music gene with her wonderful voice that Bentley showcases on his Instagram. She is also no stranger to performing on big stages with her dad and even on smaller locations. 

And then, on Christmas day of 2010, they welcomed their second child Jordan Catherine. She is pretty much out of the limelight, but she sometimes pops on his dad’s Instagram just having a good time with him. 

Three years later, on October 9, 2013, the couple finally welcomed a boy into the family. Knox, who is now seven years old, is following in his dad’s footsteps when it comes to adventure and hockey. And if you’ve watched Bentley’s official “Livin’” music video, then you definitely saw him already as he co-starred in it. 

Needless to say, the family looks tight-knit and are busy enjoying their life together. 

Third Chapter: Making Up for Lost Time

Last spring break, the family went to Colorado to spend some time. But as the pandemic worsened and the restrictions became even more strict, the family decided to stay in Box Canyons. 

He returned a few times to Nashville for work, but he was really trying to maximize his time with his family to bond with them. In an interview, Bentley said that he wanted to make up for the lost time after being on tour for 18 years and being away from them every weekend. Now, he would ride his bike with his kids to school. He even put a camper on the back of his 1994 Chevy, and Dierks Bentley and his wife Cassidy Black, along with their three kids, went camping almost every weekend. 


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Cassidy Black, Dierks Bentley


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