The speaker sits on a curb in Washington, D.C., drinking cheap vodka with a homeless man named Francis, and the day slides from ordinary city life into dream logic. Shops turn into Hebrew letters, penguins gather at a fountain, and Shakespeare turns up selling drugs. Despite the title's promise of an "insider's guide," nothing here is practical or official. The city looks like a place where nothing quite holds still.
Underneath the jokes, the speaker seems restless and a little guilty. A line from her father about never having known hard times hangs over the scene, and the poem seems to ask what it means to play at being an outsider. She asks Francis to teach her to panhandle, and at the end she says she pours her "insincerity" into books. The mood is playful and absurd, but there's an uneasy, self-mocking edge, as though the speaker doubts her own place in the world she's wandering through.