Maxine resists Gillian's home grown cardiac rehabilitation program; Lauren tells Amy that she wants to live with Michael; when Vincent comes to Sean looking for work, Sean refers him to Crystal Turner, who runs a outreach program for homeless teenagers; David quits his job and takes off for the Caribbean on his sailboat; Amy must decide whether a depressed woman with multiple sclerosis is well enough to care for her ten year old son; Vincent offers to tutor a homeless teenager studying for his G.E.D., but when he tries to get the boy off the street and into a group home, the boy disappears.

Amy learns that she is pregnant with David's baby after taking a home pregnancy test, resulting in David returning from his sailing trip to discuss with Amy their future together and what they mean to each other; Maxine's first case back since her heart-attack involves a seventeen year old single father; Amy presides over a case involving a boy who stabs his teacher; Vincent and Crystal take a ten year old prostitute to the hospital after being beaten up by her pimp.

When Amy tells Lauren about being pregnant, her reaction is not exactly what Amy would have liked; While working at the outreach office for teenage runaways, Vincent uses his flair for writing to encourage a teenage runaway to write a better essay about himself so that he will be accepted in a half-way house; Amy presides over a case involving parents who want to terminate their custody over their adopted child due to his short temper and destructive behavior; Maxine deals with a case involving a boy who uses his eight year old foster brother as a drug mule; Peter fears for his relationship with Gillian when all she wants to do is have sex; Amy and David become engaged.

Unaware that he is hiding his true feelings and pretending to be happy for her, Amy is annoyed by Bruce's casual response to news of her engagement. Amy is also annoyed that her relationship with Bruce has evolved to the point where he knows all of her idiosyncrasies, including, he asserts, how she'll rule in the heartrending case of a teenage girl with epilepsy whose parents disagree about whether or not she should have risky brain surgery that may stop her seizures; Elsewhere, Maxine has issues with an affluent, mostly white prep school after a student there is severely beaten; a publisher takes an interest in Vincent's new book; Lauren lashes out at Amy for being pregnant.

Amy oversees an emotional case involving a 13-year-old boy with a history of violent behavior who shot and killed his grandfather who was suffering from terminal lung cancer; Maxine uncovers a human smuggling operation while following up on a report of a young boy being beaten numerous times; Vincent witnesses the gunning down of a prostitute by her pimp; Meanwhile, Amy and David search for the perfect house to start their life together in.

Several weeks have passed since Amy's miscarriage, but things are not quite back to normal for her. She refuses to discuss the house with David and brushes off Bruce's admonition that she's becoming too close to Graciela. Maxine meets up with a high school friend at a wedding and discovers that her recent divorce has left her depressed. Maxine helps her reconnect with the world by getting her involved at the hospital - holding HIV positive babies to stimulate their growth. Crystal invites Vincent to come to her AA meeting marking 30 days of being sober and they begin a new phase in their relationship. When Graciela is arrested for being in the car during a drive-by shooting, Amy goes all-out to keep her from being tried as an adult. Bruce asks her not to get too invested because he doesn't want to see her ""lose...again,"" which unfortunately, she does. David returns Amy's half of the deposit on their dream house and tells her that he thinks they should take a break.

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