In Billie’s freshman year of high school, Wade moves in with her mother. Meanwhile, Cassie and Kyle have been dating since the homecoming dance. Billie likes Kyle, and Cassie seems to love him until they visit her paternal grandmother in Greenwich. Cassie and her parents lived near Grandma Catherine in Greenwich until her father, Eric, lost all his inherited money through bad investments. Grandma Catherine cut Eric off, and the family moved to Red Hook. Although the rest of her family is estranged from her grandmother, Cassie has kept her favor. During lunch at an expensive restaurant, Kyle visits the restroom. While he is gone, Grandma Catherine comments on his dirty fingernails and cheap-looking clothes. Afterward, Cassie looks dejected and admits she is having second thoughts about Kyle. When they return to Billie’s house, Billie is puzzled when her mother mistakenly asks Cassie the same question three times.

Billie and Alex arrive at Cassie’s dinner party. Cassie and Grant live in a penthouse apartment in Gramercy worth $7 million. Several other couples are there, including Cassie’s friends Ava and Blake, who also have rich husbands and small babies. Billie glimpses a Hispanic woman in the kitchen, and Cassie reveals that Lourdes is her housekeeper and nanny.