Sixteen years later, Anna moves to New York for work and calls Jake and Brian out of the blue, rekindling their friendship. Anna and Jake begin sleeping together, but he is reluctant to become seriously involved as she is not Jewish, which could compromise his relationship with his congregation and his mother Ruth, who disowned her eldest son for marrying outside the faith. Between this conflict and their desire to spare Brian's feelings, the relationship is kept mostly secret. As the relationship continues, Jake remains unwilling to view the relationship as serious, despite Anna’s hints at her ‘taking a class’. She is upset when they run into members of Jake's congregation while on a date, and Jake introduces her only as "my old friend Anna".