After Dean Lewis' father received a bleak cancer diagnosis, the Sydney-born singer-songwriter feared the worst. He considered his dad his best friend and the person he most looked up to, so when doctors gave him a 25% chance of living past a year, Lewis was heartbroken. He wrote "How Do I Say Goodbye" about coming to terms with his father potentially passing away.
Lewis wrote the song in Nashville with Jon Hume after his father had been in remission from cancer for six months. Hume also co-wrote Lewis' "Hurtless"; his other credits include JP Cooper's "September Song" and Sofi Tukker's "That's It (I'm Crazy)." Lewis penned the song from the perspective of when he still didn't know if his father was going to die.
When Lewis recorded the song, Hume set a mic up in the middle of the room. Lewis sang the chorus twice, took off his headphones, then Hume played it back to him. He couldn't believe what he was hearing from the speakers. "It was so powerful that we were blown away and I was crying," Lewis told Apple Music. "I think I cried 10 times, and I just sat there listening to the chorus over and over again. I could hear the emotion in the chorus, and it captured what I wrote the song about: my mum telling me, 'You have to come home.'"
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