The most affecting moment on Guitar comes 45 seconds into the fourth tune, “Nightmare.” The song begins mid-meter, DeMarco’s voice arriving so ahead of the beat that it’s like he has been searching for someone he can tell his troubles to. Maybe there’s been an argument, and his partner is still sleeping it off in the next room. It is a miracle, he confesses, that she sticks around at all. “Roll up those sleeves, boy,” he sings in a diminutive falsetto, cuddly as a teddy bear. “Smoke the whole pack/There’s no turning back from this one.” In a few perfect lines, this is the war of always trying to get your shit together, of trying to be good enough for the life into which you have wandered. By all interview accounts, DeMarco’s partner, Kiera McNally, possesses a saintly forbearance, sticking with him from those rough-and-tumble salad days to these idyllic times of pruning olive trees on an island; here he is, waking up bummed, then rolling up his sleeves to try and deserve her.

In two minutes, “Nightmare” bottles both sides of Guitar—DeMarco’s bummer survey of what he has been and his grim commitment to what he may still be. The past comes back to haunt him on “Knockin’,” a simple country-funk number where regrets he thought he’d overcome arrive like uninvited guests for a housewarming party at the spot where he hopes to spend the rest of his life. Evoking George Harrison on a morphine drip, “Home” finds him contemplating the places and people he’s already left, how seeing them again would feel like finding a ghost whose sole purpose is to remind him of his failures. Each beat is another towering speedbump that DeMarco is willing himself over and beyond, forcing himself into the future.

And DeMarco’s songs about that future are what make Guitar so endearing, what makes it land like a long hug from an old friend you assumed you’d never see again. “Sweeter” seems like a catatonic bummer, a from-the-brink testimonial of someone who has supremely fucked up, repeatedly breaking a lover’s heart until she vanished. But DeMarco’s promise—“This time, I will be sweeter/I can be much sweeter/Some things never change”—is so plainspoken and earnest that I find myself pulling for him like he’s some hapless sports team, one play away from saving the franchise. He searches for his core on “Punishment,” a sort of secular prayer about trying to find the thing that animates you, the thing that can serve as a safeguard against your worst instincts. Plodding in a way that suggests a daily ritual, “Holy” is more direct still, a plea to be cut free from the “curse from down below.” DeMarco can see the tether to his old ways starting to fray; just maybe it will finally snap.

DeMarco’s first album arrived the month I got engaged, his second a month or so before I turned 30 and got married. When his songs were daily reckonings with nights of excess, I was trying to get over inherited bacchanalian patterns of my own, to ease into some version of adulthood. His music made me feel like I was staring into some cracked rearview mirror. I get the sense from Guitar that DeMarco now knows what that’s like, as one tries to leave the pernicious habits that extend from a lineage of addicts. But these songs—soft lullabies and blues for himself about the hard places he’s been—make me think he’s getting somewhere new by being honest and at least a little optimistic. “All those days of trying to run/What a waste of breath,” he sings at one point, like he’s letting out a sigh he’s suppressed for 35 years. Maybe no matter the struggle, you could still be a little like this version of Mac DeMarco, too.