Country Singer Russell Dickerson Looks Back on His Wedding Day Nearly Five Years Later

Kailey and Russell Dickerson Wedding. (Credit: Spencer Combs Photography)

Updated Feb 12, 2018

Country singer Russell Dickerson isn’t a big planner, but what he lacks in foresight he more than makes up for in “aww”-worthy delivery. When the “Yours” crooner decided to pop the question to his then-girlfriend, Kailey, he gave her best friend exactly 30 minutes to get to the scene of the proposal.

All About Minka Kelly's Boyfriend, Dan Reynolds

“We had looked at a ring, but my best friend had just gotten married the day before and he knew I wanted her there [for the proposal],” Kailey tells The Knot. “So I was thinking even though he got the ring a few week ago, there’s no way … he’d probably wait until she got back from her honeymoon. But sure enough, [her best friend and her husband] walked through the sliding door of my little crappy apartment.”

“Russell texted them and was like, ‘I’m about to propose, can you guys be here in 30 minutes?’ And they hadn’t left for their honeymoon yet. She was like, ‘Can we shower first?’ so she walked in with wet hair,” Kailey added.

All About Minka Kelly's Boyfriend, Dan Reynolds

Russell, 30, staged the proposal in a manner that was very “them”: by asking Kailey, who had just gotten up from a nap, to help him film a video for YouTube. When Kailey set the camera on a tripod, she had the lens set up to zoom in on Russell; the singer asked her to make it a “wide angle” instead, and the pair bickered.

Finally, Russell tells us, he walked over, picked up his guitar, and sang a short three-line ditty, ending with a proposal to Kailey.

The couple’s wedding was one big whirlwind as well, with both Kailey and Russell improvising throughout the day. At one point, they tell The Knot, they ducked away from the celebrations to go take impromptu photos in a field near their Nashville reception venue, the Houston Station, where they had previously staged their engagement photos.

“On our wedding day, we didn’t really plan it, we said, ‘Let’s see if we can go back,’” Kailey says. “And as we pulled up from the ceremony—we’re in a trolley, mind you—we leave it on the side of the road and started walking and this woman pulls up.”

The pair asked the woman if they could take photos in the field, and she responded that it shouldn’t be a problem, even giving them the gate code to the property to take more photos. Kailey calls the resulting images “magical.”

But perhaps one of the most magical moments of their big wedding day was also one of the quietest. Instead of exchanging personalized vows before their 650 guests, the couple opted to instead exchange letters.

“We exchanged letter and closed our eyes and read our letters with our backs to each other,” Kailey remembers. “Then we held our hands and prayed, but we didn’t see each other reading the letters.”

Now, looking back upon their nearly five years of marriage, both Kailey and Russell have plenty of wisdom to impart on newlyweds.

“Always take the low road. Always choose humility,” Russell says. “That’s, like, the hardest to do but the most effective.”