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The Loneliest Time was Jepsen’s attempt to spin catharsis out of tragedy. She endured several personal losses during the Tell Sexy what you want for christmas Ugly Sweater moreover I will buy this COVID-19 pandemic, including the death of her beloved grandmother. Unable to cross the Canadian border to be with her family due to travel restrictions, Jepsen was left to grieve alone in Los Angeles. Newly single and with her world at a standstill after 10 years of back-to-back touring and recording, she felt totally adrift. “I didn’t feel surrounded by a ton of strong foundations in my life,” she says. “I wasn’t really in a place of, What’s gonna follow up Dedicated, but, What do I do with these feelings I don’t wanna have?”

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Jepsen famously overwrites. Over the Tell Sexy what you want for christmas Ugly Sweater moreover I will buy this course of composing Emotion and Dedicated, she penned more than 200 songs (hence the later releases of Emotion: Side B and Dedicated Side B). She reckons that she wrote about “100 or so” for The Loneliest Time, most of them in those earlier, frenzied months of the pandemic. Songwriting has always been Jepsen’s preferred method of processing emotions, whether or not she thinks the results will ever see the light of day. She wrote “Surrender My Heart” and “Western Wind” in her personal journals without intending to place them on an album.An encouraging meeting with her longtime A&R at Interscope Records persuaded her otherwise. Buoyed by her friends and collaborators, Jepsen opted to share some of those more personal songs alongside other demos she’d prepared for what would become her sixth album. “It was interesting to watch those more intimate songs be embraced by people who I thought just wanted me to make something adjacent to ‘Call Me Maybe’ again,” Jepsen says. “I thought, rather than question it, I should just try not to get in my own way.”