At Tripp's behest, Nick travels to a vineyard in Italy to meet with a spy who may know more about the death of Nick's father. Nick appeases his wife Lisa's annoyance with his focus on the Darlings by taking her with him. But their romantic idyll is broken -- repeatedly -- by Karen and Freddy, who decide to tag along everywhere. Letitia confirms to Tripp that she had been unfaithful to him throughout their marriage. Heartbroken, he becomes hell-bent on determining if all of his children are biologically his. Meanwhile, Jeremy struggles to keep his affair with Juliet's archenemy a secret, and Brian Jr. needs his dad's help to battle a bully at school.

Unbeknownst to Tripp, Nick finds himself in full damage control mode when a blackmailer surfaces and demands ransom for a sex tape featuring one of the Darlings. Meanwhile, Patrick is forced to break off his affair with Carmelita, plunging him into deep despair; Brian's wife figures out that the "Swedish orphan" he brought to live with them speaks English; and Jeremy struggles to keep his assignations with Juliet's archenemy, Natalie, a secret -- but when both women show up at Patrick's Senate campaign fundraiser, a red carpet catfight ensues.

Nick tries to find out who killed his father with the help of airplane mechanic and Darling aficionado Norman Exley. Juliet sulks in her new luxury hotel digs and refuses to participate in an important high-end photo shoot for the family involving trained lions. Tripp pressures Patrick to announce he's running for the Senate, even as his son continues to woo his secret lover, the transgendered Carmelita. Jeremy strikes up a secret romance with Juliet's biggest nemesis, notorious celebutante Natalie Kimpton, and Brian drops his illegitimate son in Nick's lap.

As a boy, Nick George watched his father surrender his freedom and family as the trusted consigliere to the absurdly rich Darlings of New York City. Nick grew up being second to the overpowering family. Burned by his boyhood encounters with them, the idealistic Nick did a 180-degree turn and became a lawyer for the disadvantaged. After the death of his father, family patriarch Tripp Darling offers Nick the opportunity to inherit the responsibility of being the family lawyer and protecting the Darlings' secrets. But the ungodly salary that will allow Nick the freedom to be an altruistic do-gooder is only part of the picture. As he finds himself racing to plead with cops, hush the tabloids and furiously try to wipe the mud off the esteemed Darling reputation, Nick wonders if he has gotten the chance of a lifetime -- or a life sentence.