Roy Woods’ superpower has always been transparency. Across his 2016 debut, Waking at Dawn, the Ontario native wrestled with the temptations and privileges of being a rising R&B star. He was a 20-year-old trying his best to stay true to his innermost desires. Nearly a decade later, on Dark Nights, the singer has grown, but his search for love hasn’t gotten any less complicated. Album opener “So Obvious” sets the tone: “Summer’s over/It’s so obvious,” he croons over a hard-hitting backdrop courtesy of frequent collaborator Dimi. We're hearing him realise relationships can be as fleeting as the seasons. But Woods is nothing if not self-aware. He looks inward on “Stay With Me”, owning up to the strain his career puts on his relationships. “What I Used to Get Into” is likewise an attempt to start fresh, the singer confessing to past mistakes as a way to move forward. At just nine tracks, Dark Nights is dense with moments that feel deeply reflective. Album closer “Tell Me What I’m Living For”, for instance, is Woods reckoning with his life’s choices, still wondering when it’s all going to make sense.