Esther Rose Embraces Messy Feelings on ‘How Many Times’

Esther Rose is, as they say, feeling all the feels. Her new album, How Many Times, chronicles the messiness of being a work in progress, in relationships, in personal growth, as an artist, and a human being. Humanity runs deep in Rose’s songwriting. She knows just how to capture all of its little injustices, humilities, and heartbreaks, but also its glowing sparks. Though How Many Times finds her navigating the end of a relationship, it is a study in sitting with yourself, getting comfortable with the loneliness, and then dusting yourself off and dipping a toe back in.

That line between thoughtful trepidation and wild fearlessness is one Rose teeters along gracefully with her golden toned voice and gentle guitar strumming. She especially shines in the quieter contemplative moments of How Many Times, like in “Songs Remain,” in which she’s able to look back on a painful breakup warmly thanks to a little perspective. “To know you is to be forever changed / I am glad it was you who broke my heart,” she sings. We don’t get the sense that she arrived at this conclusion without a few bruises and plenty of tears, and that’s what makes it sting so beautifully. Perhaps the album’s title track was a stop along the path to this place of acceptance. In it, Rose repeatedly laments, “how many times will you break my heart?”, weighing her options for numbing the pain before ultimately deciding to just feel it instead. By the time she breaks out the “sha-lala-oooh” finale, we hear her letting it go.

For all it’s working through, How Many Times is a mostly up-tempo record, and Rose excels at a waltzy country sound that makes you want to take to a dancefloor and sway, beer in hand. “Keeps Me Running” uses a fiddle to create a driving melody, and “Coyote Creek” creeps up low and slow before its hazy chorus. “Good Time” meets Rose stranded on the side of the road with a broken-down car, exhausted from a long stretch of driving, laughing at this bout of bad luck. “It’s a real good time for bad timing / amen,” she sings. And “Are You Out There” moseys through an evening of uncertainty and hopefulness about what’s to come. It is wistful, not ready to give up, but okay to take its time.