“I was beguiled walking into FitzGerald’s. It was a high quality introduction to songwriting. That really made me really start to write,” said Ashley, who up to that point had spent most of her life in Moville, a small town in western Iowa where her family grew soybeans and corn.

City life was new. At first, she pursued a career as an actor in Chicago; the experience led her through some familiar paths for any hungry actor: She performed in improv, in children’s shows and comedy cabarets and with groups such as Noble Fool Theatre and the Neo-Futurists. She also wrote shows and helped create The Bowling Show, a partly improvised show that ran a full year at Timber Lanes Bowling Alley in North Center.

The do-it-yourself nature of the Chicago storefront theater scene was inspiring — “You could just decide to write a play and put it on in a bowling alley and run it for a year. It was crazy,” she says now — but it also happened to give her the fortitude needed to pursue a career as a musician, a path she viewed as fully independent.

“I wanted to just do my own thing and not be reliant on trying to get into somebody else’s thing. That made me leave theater. It never felt authentic. I couldn’t figure out how to be myself,” she said. “With music I can be fully myself. So that became more and more important.”

She went on to become an omnipresent figure on Chicago’s club scene, now playing in four different bands, including the cover band Real Pretenders. Her voice has been compared to that of Pretenders frontwoman Chrissie Hynde, and at times on this album, Ashley’s vocals can give Hynde a run for her money. There’s a snarl in her voice in playful songs such as “I Wanna Know Everything” — “I know I’m looking at you like I’m gonna eat ya / I can’t help it you’re just so sweet / I don’t just want a bite / I want the recipe,” she sings.

Despite earlier recordings from as far back as 2006, the songs on Love Bug feel like a new beginning for Ashley. The pandemic gave her the freedom to experiment with a different set of musicians, namely guitarist Jon Williams, bassist Josh Piet and drummer Jason Batchko. Eventually she took the new band to Kingsize Sound Labs, the legendary Chicago studio, where she captured the players together in “a big live room” with recording engineer John Abbey.

The musical touchstones of Love Bug are Lucinda Williams, John Prine and Patty Loveless, among other country traditionalists with strong roots in folk music storytelling. The seductive rockabilly noir of the title song opens the album, but from there the songwriting takes listeners into unexpected places.

“Seeds of Doubt,” a ballad, is steeped in gothic imagery that describe a relationship left to decay, while “Bits and Pieces” is a collection of memories — “red cigarette sparks / sirens in the Dark / olive drapes / great escapes” — that together suggest haunting loss.

“Keep My Secrets,” a country duet with her guitarist and real-life partner Jon Williams, is a testament to fidelity — but with limits. “I wake up early in a cloud of memories / with that old flame blowing with the breeze,” she sings, with phrases from Brian Wilkie’s pedal steel guitar dancing underneath. “I love you but I’m gonna keep my secrets.”

She carried the title phrase with her for eight years until she started to draw pictures to unclog ideas. The man in the song, she realized “was hiding pain” while the woman “was hiding love.” Once she visualized each perspective, the song came to life.

Ashley’s own love story weaves throughout the album and her live stage performance. Williams, her guitarist and duet partner, came into Ashley’s life in 1999 when they dated a few months. They later reunited in 2019 and have remained a couple ever since. Originally from Ohio, Williams rotated through alt-country bands like Mount Pilot and Andrew Bird’s Bowl of Fire; like Ashley, he too is a journeyman throughout Chicago, playing in several Americana bands in town while serving as the primary guitarist for Ashley’s solo projects.

She said it took a long time to find someone like him who understood how to “support the songs” and not try to compete with them. “He’s an incredibly intuitive player that’s very understated. If you know Jon and see him play, he’s not going to be showy about it,” she said. “That’s been the real joy of playing music together.”

Williams, 53, said their shared musical influences make their collaboration work because there’s always agreement. “She has a great gift for clever turns of phrases and telling stores within short confines,” he said. The music on Love Bug gives personality to those stories, allowing both the feisty humor and sobering moments to come alive. The love songs are multidimensional, which makes them far more satisfying than the typical fare on the pop charts. After years on stages in theaters and music rooms, Ashley, 49, said her songwriting has become more focused because, as with great relationships that deepen with age, her standards are now higher.

“As we all have, I’ve gone through some stuff. I’ll be 50 this year. This is age when you’ve accepted everything, you’ve moved through it, and now you can be here in the real world as you are,” she says. “And there’s a lot of joy that comes with that.”

If you go: Naomi Ashley performs 8 p.m. Wednesday, Feb. 14 at FitzGerald’s (6615 Roosevelt Road, Berwyn), with Ernie Hendrickson opening, and at 7 p.m. on Friday, Feb. 16 at Rattleback Records in Andersonville (5405 N. Clark St.).

Mark Guarino is a journalist based in Chicago.