“The Next Eight Days” encompasses the time after Jack’s diagnosis. On Monday at lunch, Kam and Seth give Jack a hard time about Libby, but Jack has the confidence to stand up to them and defend Libby. Emboldened by his feelings, he asks Libby on a date after Conversation Circle. That night, after a brief chat with Libby’s dad, Jack takes Libby to Clara’s Pizza King in Richmond. However, he regrets taking her so far from Amos, worrying Libby might think he is ashamed of her. Jack redeems the date by activating the jukebox and dancing with Libby in the middle of the restaurant.

At school, Caroline confronts Jack about dating Libby. Confident in his feelings for Libby, Jack basically tells Caroline that it is none of her business; he later tears up the “Top 10 Reasons to Date a Fat Girl” list that Seth Powell had given him. On Saturday, Jack’s mom tells him to pick up Dusty from a friend’s house. Meanwhile, Libby auditions for the Damsels after one of their members moves away. Despite delivering an energetic performance, Libby has her hopes dashed when Caroline publicly questions whether Libby’s weight will impede her ability to serve on the drill team.