After her brother Richard arrives in town looking for his son, Maxine initially refuses to put him in touch with Kyle, but later relents; in the process of helping Donna with her estate planning, Peter and Gillian agree to become Ariadne's guardian should something happen to Donna; as Maxine quarrels with Richard about the event that caused them not to speak for twelve years, it becomes apparent that Maxine blames her brother for Edward's early death; Bruce and Andrea hit it off during a play date for their daughters, and later go out on a date; Kyle refuses his father's offer to bail him out of his troubles; Maxine works to help a father regain visitation rights to his teenaged son; Kyle and Amy continue their discussion about the events that caused a rift in their relationship and find that they share responsibility and guilt for the events of that night; a young surrogate mother pregnant with twins who has no interest in keeping the babies comes before Amy in the middle of a custody

Barry invites Amy to a business dinner, where her outspokenness almost gets the better of her and the budding relationship with Barry; with Kyle's help, Maxine searches the streets for a runaway gay teen, and she later agrees to let him stay at her house until she finds him another foster home placement; Amy must decide if a teenager who wrote a play about killing bullies, joked about school shootings, and considers the Holocaust a warning to the ruling classes, presents a threat to society; Maxine's already strained patience with the way Brian is running Teen Harbor snaps when she witnesses a drug deal there, and she orders it closed, incurring Kyle's wrath; as Bruce prepares a recommendation for Amy on whether a woman whose alcoholism caused her to lose custody of her children should be reunited with them, he isn't entirely convinced that she has stopped drinking and decides to do a little surveillance, bringing along Andrea to keep him company.

Maxine reluctantly allows Eric to stay at her house when she's unable to find him the right placement; Amy makes a second date with Barry; Kyle helps a former drug addict who goes to extremes to find an apartment; Amy hears the case of a teen who is suing a tobacco company for causing his emphysema; Gillian's effort to expand her knowledge of black culture doesn't go so well.

When a teenager whom neither parent wanted and Amy placed in a locked facility escapes and comes into D.C.F. with bruises she says were caused by abuse at the facility, Maxine's decision to have her returned to the facility leads to tragedy; Amy attends the tenth reunion of her Harvard Law School class and is disheartened by how petty, mean-spirited, and sleazy her former law school best friends have become, until Barry shows up unexpectedly as her white knight and saves the day; Michael makes it obvious that he is still attracted to Amy, and expresses regret over their divorce and his marriage to Leisha; Maxine scoffs when Sean has all the files computerized, but changes her tune when he swiftly downloads information which helps them identify and locate a suicidal teenager.

Maxine is saddened when Jared fails to call her upon his return from China, so Sean arranges a casino night fund raiser to cheer her up; a born-again teenager charges her mother with parental neglect for working as a stripper, and Amy must decide whether to place the girl in foster care; Donna confronts Kyle after she finds a syringe and morphine in his room drawers and is relieved to hear that he keeps it as a reminder that he is capable of making the choice to stay clean every day; after his daughter tells him about her ill-timed encounter with Bruce, David Solomon files a complaint against Andrea, who immediately ends her relationship with Bruce for fear of losing custody; responding to a message from Bruce attempting to explain the situation, Solomon shows up at the courthouse and threatens, taunts and insults Bruce, who is arrested and jailed after he knocks Solomon to the ground with a punch.

Amy, Maxine and Lauren have trouble adjusting to their new living arrangements; Vincent returns for a visit to smooth over the waters between his mother and sister and persuade them to live together again; after Lauren tearfully calls Michael about the move, he suggests to Amy that Lauren come to live with him; Amy presides over a custody dispute involving a father who refuses to take a paternity test; Donna dates one of Amy's law school classmates; Amy ends her relationship with Barry.