ET caught up with the 31-year-old "Yours" singer and he opened up about his online friendship with the Bachelorstar as well as his break into country music and upcoming tours. The guys share a mutual friend and were connected online after Dickerson reached out on Instagram.
"He’s like, ‘Dude, your album. I listened to it the entire season.’ I was like, OK!" Dickerson excitedly revealed. "We just text back and forth a little bit. He’s super cool."
As for how he thinks his buddy is doing so far on his season, Dickerson had nothing but praise for Underwood.
"I think he’s a great dude," Dickerson said. "I think he’s super genuine. He helps people open up. As opposed to some people in the past that are just so shallow where it’s just like, ‘Oh my god.’"
"Especially my wife, she’s like, ‘Oh my god. Nothing’s going on in your mind or heart or soul,’" Dickerson said of Kailey Dickerson, his wife of more than five years.
When the couple isn't watching The Bachelor, they're busy collaborating through Dickerson's music. The "Blue Tacoma" singer told ET that his wife often directs and stars in his music videos, something he credits to their success.
"I could sing to Joe Schmo behind the camera or I could sing to my wife. I really think that’s the kind of intangible element of the 'Yours' video. I'm singing to my wife," he said of his debut video, which he released in 2015. "Not a lot of artists can say that, maybe none, that they were singing to their wife while filming."
The video was filmed on "a shoestring budget" and no backing from a label, but the couple made it work, with Dickerson channeling the lyrics that he wrote about his better half.
"When you meet someone like that and get married -- we were newlyweds when I wrote the song -- it’s just, like, all of these selfish instincts in us just kind of go away, either naturally or you learn to make them go away," he said. "... I mean, she’s taken pictures on the road since we started and she sold the merch and she’d help drive the van. She’s a trouper."
When "Yours" hit number one on the country charts in 2018, it was the accumulation of "eight years of working my butt off to finally start to pay off." That feeling was only increased when his second single, "Blue Tacoma," peaked at number one later last year.
"When ‘Blue Tacoma’ went number one, that was the one where I got texts from people in the industry and they’re like, ‘Welcome to the big leagues,’" he recalled. "‘Cause one could be a fluke. One could be a free hall pass… But when you have two in a row, that’s, like, this isn’t a joke. That was a huge moment for me."
With his current single, "Every Little Thing," climbing the country charts, Dickerson is on his co-headlining tour with Carly Pearce. The pair opted to call their string of shows The Way Back Tour, in honor of knowing each other for more than 10 years.
"I couldn’t be happier. It’s super special... Not a lot of artists touring together can say they go this far back," he said. "I love her. She’s a star."
"We just poured our heart and soul into this new headlining tour. I’m so pumped," he added.
When The Way Back Tour wraps with a sold-out show in Chicago, Illinois, on March 2, Dickerson has a couple of months off before hitting the road again, this time with Thomas Rhett. The pair previously toured together in 2017 and 2018, but this time it'll be "completely different" for Dickerson.
"We toured smaller arenas, but now we’re coming to Madison Square Garden," he gushed. "... I couldn’t really bring a lot to the table [before]. I was super new. ‘Yours’ hadn’t even gone to radio yet... Now I can bring something to the table. I can help sell tickets. I can honestly have a little more say in what my show looks like. I can afford lighting now. I can really make this show my own and that’s what I’m so stoked about."
Though fans will likely have to hold out until 2020 for new music from the "Billions" singer, he assured ET that the new songs -- some of which he wrote with Lady Antebellum -- will be worth the wait.
"We wrote a ton of songs this summer. Wrote a bunch with Lady A and my normal team," he revealed. "We wrote all tour and, god man, the stuff that we got, I can’t stop listening to it. I’m super pumped."