Giving a nod to The Decameron and The Divine Comedy, Last Time Around moves through three sections or "books," as the four central characters travel from German beer garden to Brooklyn music venue to Polish diner. Along the way, the characters eulogize and disparage former acquaintances, lovers, and total strangers in an attempt to mask and skirt around the tender spots in their own lives. The book's narrator, Ian, is himself going through a significant period of change when the novel opens. He is starting a new job, moving apartments, and attempting to get over his ex-girlfriend Olivia. Introspective by nature, he grasps the night's significance when he realizes his friends are also moving in their own directions. Hovering on the periphery of the evening is Nick Amante, Ian's undergraduate nemesis from Yale-a vague, stalker-like person and double for Ian. Amante is a young writer whose most recent book, Inferno, has earned minor recognition. Even while Ian dismisses Amante as a hack (quoting liberally from Inferno's most purple passages), it becomes clear that Amante has a guide-like role to play in Ian's life. The night ends in a room full of fake mariachis where Ian finally connects with Amante and Olivia, and receives the inspiration to write his own story.