At Cool Beans Café, Jo orders her nostalgic high school drink and is surprised when Van Erickson, her high school and college boyfriend, appears behind her. He is friendly and charming, and their shared history rushes back to Jo, including their breakup two weeks after college graduation when Van revealed future plans that did not include her.

They exchange updates: Van lives in Boston and is back to help his parents move; Jo confirms she lives in Los Angeles and writes songs. Van pays for her drink, recalling how Jo used to cover his in the past, and compliments her music, even the new love song, which surprises Jo.

Throughout the exchange, the disembodied male voice in Jo’s head interjects commentary, analyzing Van’s wording and motives. Jo silently responds but tries to shut the voice out in public, reminding herself that her thoughts should be private.

As Van leaves, he suggests they get together and says Mitch has his new number. Jo is stunned to realize he has essentially asked her out after nine years apart, and she has a conflicted reaction—drawn by old feelings but wary because of how their relationship ended.

Jo goes to the patio to meet Gigi, who has been reading. They briefly banter about the book before Gigi confirms she saw Van leave and notes he looks good. Jo tentatively wonders if her hit song “If You Stayed” might be about Van, and Gigi turns the question back to Jo, underscoring Jo’s uncertainty about her lingering feelings and creative inspiration.