Andy Shauf’s coy, almost boyish voice sounds especially tragic when he says something that breaks your heart. Over the past few years, Shauf has perfected his signature lilt, a habit of unexpectedly pitching up the second half of a word and delicately fading it out, like the brief fluttering of wings. When he does this on his recent single “Spanish on the Beach”—stretching out “wished” and “permanent” in the line, “I wished it could be permanent”—you imagine it’s followed by an amused, self-deprecating chuckle. What a silly little thought, he seems to say.

Whispered words in a romantic language set the scene for “Spanish on the Beach,” in which Shauf’s narrator vacations with Judy, the ex who previously sent him down an 11-track memory lane on 2020’s wistful concept album The Neon Skyline. The song is deceptively idyllic: A gentle bassline pairs with easy guitar strums; maudlin woodwind drifts in for dramatic effect. Remembered images of Judy’s “long dark dress” and the musicians’ “smiling eyes” populate the song; at one point, Shauf imagines making a “mortifying” over-the-top proposal, like a scene from La La Land’s technicolor fantasy. But tucked between cool cynicism and glam surroundings are the signs of an expired romance: When Judy tries to talk to the narrator in Spanish, he “turn[s] away to watch the musicians play.” They’re doomed, and he knows it.