Nick George reluctantly accepts an offer to take over his father's job follow the death of his father in a mysterious plane crash. Now, Nick is the chief counsel for an extremely wealthy and powerful Darling family and is thrust into the world of the Darling family's numerous personal and legal issues.

Nick continues to search for his father's killer with the help of Norman Exley, a mechanic and Darling aficionado. Juliet holes up in her new luxury hotel and refuses to be a part of an important photo shoot involving lions. Tripp tries to get Patrick to announce his bid for the Senate. Jeremy begins a secret relationship with Juliet's arch-enemy, Natalie Kimpton.

Nick flies into damage control mode when a blackmailer demands money in exchange for a sex tape. Patrick becomes depressed when he has to break his affair off with Carmelita. Meanwhile, Brian's wife learns that the Swedish orphan speaks English; Jeremy stuggles to keep his affair with Natalie a secret, but Natalie and Juliet wind up fighting at a senate campaign fundraiser.

Nick travels to Italy at Tripp’s request to meet with a spy who may have information about Nick’s father’s death. To ease tensions with his wife, Nick takes Lisa with him, but his idea of a romantic vacation is ruined, over and over, by Karen and Freddy who tag along. Meanwhile, Letitia reveals to Tripp that she had had affairs throughout their marriage, leading him to question if his kids are really his or not.

Nick meets with Simon Elder, Tripp's arch-nemesis, but finds that he has more in common with Elder than he had assumed. With Juliet and Jeremy, the Darling twins, fighting over Natalie Kimpton, they opt to have separate birthday parties and are each given a $1 million budget. Each tries to outdo the other -- Jeremy throws his on the Brookly Bridge, while Juliet goes with a French Revolution theme, complete with chocolate aristocrats. Meanwhile, Brian Jr. tells Brian's wife the truth about who his father is, while Karen tries to get Freddy a membership to a fancy club.

In a poker game where the cost is $20 million to get in, Tripp is pitted against Simon Elder and some of Manhattan’s most valuable property is put on the line. If Nick is able to convince Tripp to wager his most prized property, Elder will reveal the secrets behind Nick’s father’s death. Meanwhile, Karen learns that she cannot get married for a fourth time because her last divorce has not been finalized; Juliet shows Brian Jr. the perks of materialism; a blackmailer catches Patrick and Carmelita in the act; and Jeremy gets a job as a parking lot attendant.

Karen gets cold feet as her wedding day arrives. Drama ensues as she begins to have doubts about marrying Freddy, especially when Lisa thinks Nick is the reason why. Brian Jr.’s mother returns to New York to take back her son, but Brian Sr. has finally bonded with him. Patrick’s campaign revs up, but his wife finds out about his affair through an unlikely source. Natalie Kimpton tries to fix things between her and Juliet by releasing a song about forgiveness, but Jeremy is suspicious of Natalie’s motives.

Nick and Lisa plan for a Darling-less Thanksgiving holiday, but their plans are put on hold when Tripp has Nick set up a meeting with Simon Elder at the Darling country house. During the meeting, Letitia helps Karen hatch a plan to get the man she really wants -- Nick. Meanwhile, Nick battles to keep Brian's son away from his mother, Andrea; Ellen insists on meeting Carmelita; and Jeremy tries to keep up his act as a valet on his first date with Sofa.

In a series of flashbacks, secrets are uncovered surrounding the death of Nick’s father, Dutch, his affair with Letitia, as well as his relationship with his son and Tripp. Meanwhile, Karen and Simon get closer; Brian is arrested for trying to bribe an arbitrator into giving him custody of Brian, Jr.; and Jeremy has Lisa help him keep up his charade with Sofa.

Nick learns that Simon and Karen are secretly an item, but refuses to admit it bothers him. Karen skips out on the Darling family tradition of watching The Nutcracker in order to go with Simon on a mystery date. Brian finds himself in the middle of a career crisis after being suspended from the ministry and goes to Tripp for advice. Lisa tries to help Jeremy impress Sofia.