With a little bit of rock, a hell of a lot of soul, and a throwback R&B groove, Kassi Ashton has crash landed on country radio. “Dates In Pickup Trucks,” her irresistible debut radio single dropped in February, on the eve of her own 28th birthday. “It feels powerful,” she says of the moment’s alignment. Speaking about the song’s playfulness, she adds, “I want it to show that there are many sides to me.” The release marks the critical next step for the buzzy young singer. Named to Ones to Watch lists by publications like Huffington Post and The Tennessean as well as juggernaut radio personality Bobby Bones, Ashton spent 2019 as one of the openers on Maren Morris’s GIRL World Tour. In 2018, she was featured on Keith Urban’s CMA Album of the Year-nominated LP, Graffiti U. The simmering new song, it turns out, has a surprising origin story: an uncharacteristically giddy phone call between Ashton and her grandmother. One of nine children and known for her take-no-prisoners attitude, the singer was shocked when, one day, her elder fell into a fit of giggles on the other end of the line. “She’s like, ‘Me and your grandpa went on a date last night,’” Ashton recalls. “‘I made dinner, we packed it up in the truck, and we drove around all the roads we hadn’t seen in a long time.’” Ashton got to thinking about the nights she stepped out under the stars in her own pickup, back in her one-stoplight hometown of California, Missouri. (“You can gravel road for hours, where I come from” she quips.) Ashton brought the idea into a co-writing session with Luke Laird, who, while having served as the pen behind massive hits by Thomas Rhett, Eric Church, and Carrie Underwood, is also, as Ashton explains affectionately, the “other half of my creative brain,” and David Garcia. Initially, her collaborators both balked at what they considered a kitschy title. “They’re like, ‘This is not the girl I know!’” Ashton says, laughing.