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Country’s Romantics: How Nashville’s Leading Men Found Their Valentines

Thompson Square, Dierks Bentley, Jake Owen
Jason Merritt / Isaac Brekken / Rick Diamond, Getty Images

It should be no surprise that many of country music’s most romantic singers are pretty smooth off stage, as well. However, the most memorable, real-life love stories are honest and spontaneous. They hinge on tiny details, like the emotion she stirred when she walked on his bus, or the dress she wore when he sang to her on the beach during Spring Break.

A few of these country guys had the money to afford a big diamond ring, but at least one stud didn’t, so he had to make do with glass until he could scrape together enough to swap it out. From how they met, to the heart-melting proposals and fairytale weddings, these are a few of the most romantic stories of true love, told by the famous singers themselves.

Love at First Sight

Justin Moore and Kate Moore
Michael Loccisano, Getty Images

Justin Moore won his wife’s heart with a song. She won his with a dress. It was a black and white floral dress — “sleeveless, really long,” he told Taste of Country. “Satin or silk or something. She was gonna throw it out a couple of years ago and I said, ‘You gotta keep that.’ I don’t know if she’ll ever wear it again, it’s probably not in style now.”

Kate agrees that she won’t, but smiles at the memory of the two of them — on separate senior trips during high school — running into each other along the beach. Justin sang her a song (a pop song) and that was that. Years later, when it came time to ask for her hand in marriage, he knew just where to go.

“I thought, ‘Man, that would be cool to propose to her on the beach,’ because we had not been back to the beach since we met each other,” Moore told the Boot. “My family went down without her knowing. We rented a house, we drove down, we walked out on the beach, did the whole bit — ‘Will you marry me?’ And there just happened to be fireworks going off in the background. I should have [taken] the credit for that, for setting that up, but I didn’t.”

On the day they married — barely 15 minutes after the ceremony — the now-star signed his record contract. The couple are expecting a third child in 2014.

Dierks Bentley, Cassidy Black
Jason Merritt, Getty Images

Cassidy Bentley can relate to Kate Moore’s task of taming a country wild man. And Dierks Bentley can relate to Justin’s story of falling in love quickly. The ‘I Hold On’ singer remembers having a crush on Cassidy as early as eight grade, but says he was too immature. She agreed. The two told People about their on-and-off romance that Dierks almost gave up on, because he didn’t think he could make her happy. A life with a troubadour isn’t for everyone, after all. Even though he’d write deep, heartfelt love letters and FedEx them to her, they couldn’t get past the long distance risk.

Then, he invited her to a show in Las Vegas. “When she walked on the bus, I just knew,” Bentley says. So did she. Cassidy quit her job in San Francisco to live with him in Nashville. In December 2005, he surprised her by proposing. The very next morning, he surprised her with plans to elope to Mexico that day. He even picked out the dress! Talk about brave.

Cassidy and Dierks will celebrate nine years together in December. They now have three kid, and a famous dog named Jake.

Destiny Brought Them Together

Destiny — and country music — brought this next group of country couples together, but the romantic overtures by the famous men made their meetings meaningful. Keifer and Shawna Thompson of Thompson Square started dating just days after both made separate moves to Music City. They worked as solo artists for years before becoming a duo, but they quickly became a love duo. Thompson’s proposal revolved around a pumpkin and his disgust for the gooey stuff inside.

Thompson Square
Rick Diamond, Getty Images

“We had gone to get a pumpkin to carve out for Halloween,” he told CBS Radio in 2012. “Shawna cleaned out the pumpkin, because I don’t touch the gooey stuff. I had put the ring at the bottom of the pumpkin and [when] she came back to put the candle in she pulled it out, bawling.”

One problem … Keifer was broke at the time, so he had to ask the ring-maker to put a piece of glass in the setting instead of a diamond. “The week we got married, I replaced [the glass] and said, ‘Let me get your ring cleaned, it’s so dirty!’ I switched it to the actual diamond and she said, ‘Wow, it’s really clean now.’”

Brad Paisley and Kimberly Paisley
Terry Wyatt, Getty Images

Destiny and persistence brought Brad Paisley and Kimberly Williams together. These days, their courtship is famous. He fell for her watching ‘Father of the Bride,’ and as soon as he could, he cast her in a music video so they could meet. It worked, although their first official date was a blind one, set up by the actress’ manager.

“I was kind of sneaky when I asked her to marry me,” Paisley later told CMT. “She thought I was in Nashville at a No. 1 party. She went to a fake meeting in L.A. with a potential new publicist, and I showed up instead.”

Both of them were sneaky when it came time to marry. Friends and family thought they were gathered for rehearsal when the couple pulled a switcheroo and got hitched that very night. It made the event less stressful.

A Good Business Decision

A few country singers scored by casting the right girl for their music video, including Granger Smith, who fell for wife Amber on the set of his ‘Don’t Listen to the Radio‘ video. Five years later, they’ve got two kids and a great love story to tell. ‘Georgia Clay’ singer Josh Kelley has a similar love tale — he cast future wife Katherine Heigl (‘Grey’s Anatomy’) for a song called ‘Only You.’

“I didn’t hire her,” he told the Boot. “Somebody else did. Somebody else at the label hired her to be the leading lady. I always joke that I got her at a pretty low rate, because she didn’t hit big yet. I got her for like 20 grand, which is a pretty good buy, probably the best deal I’ve gotten in years. [laughs]“ Heigl would go on to become a very famous actress.

More famous, however, is Jake Owen, who met future wife Lacey Buchanan on the set of ‘Eight Second Ride.’ When you watch the video again, it’s clear there is some special chemistry bubbling between them. By the end, the two are crawling on each other like snakes in a barrel.

Owen and Buchanan were engaged in April 2012, when he dropped to one knee on stage and asked her to marry him. They’d wed two months later in Florida and welcome baby Pearl at Thanksgiving.

Jake Owen Family
Rick Diamond, Getty Images

Next: Listen to the 100 Best Country Love Songs

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