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.
Tripp and Letitia Darling throw Nick a lavish birthday party on a yacht, despite the fact that the day before, Nick and his wife, Lisa, had been planning to celebrate privately. That was before Tripp called Nick to broker a reconciliation between himself and his eldest son, senatorial candidate Patrick, who's going through a rough patch in his own marriage as he searches for his missing transgendered mistress. Meanwhile youngest son Jeremy reveals his feelings for Lisa to the lovely and mysterious Nola Lyons; the relationship between Karen and Tripp's nemesis, Simon Elder, enters a new level of intimacy; the de-frocked Brian is reunited with his illegitimate son; the whole Darling family is dealt a blow by the death of one of their own, and someone is arrested for murder.
The newscasts report and speculate on the fiery demise of the Darlings' Valhalla estate, as well as a Darling's death in the fire. At the same time, the family must also deal with funeral arrangements and the aftermath of the arrest of an unforeseen suspect in the murder of Dutch George. Brian recommends to Tripp that, in order to restore confidence in Darling Enterprises, a successor be named - a role Simon feels that Karen deserves.
Meanwhile, a smitten Jeremy learns Nola Lyons' true profession, Nick and Lisa discuss having another child, and recording artist Kenny G performs.
When Nick agrees to defend Letitia in the murder case of Dutch George, he is shocked to learn that his mother is on the prosecutor's witness list. Meanwhile, Jeremy plans a surprise concert for Nola; Patrick tries to clear his mind of his wife's death; and Brian heads to Brazil to kidnap Brian Jr.
Tripp opposes Patrick's plan to make his relationship to Carmelita publicly known and Ellen's bother's demand to know how his sister died. Meanwhile, Nick and Lisa head to couples therapy; Jeremy works to lessen Lelita's house arrest restrictions; and Brian Jr. is suddenly missing.
Nick faces an uphill battle as he defends Letitia in the murder case. However, the tides change when Nick uncovers a secret about Nola. Meanwhile, Karen asks Nick to tell Tripp that she's marrying Simon Elder.
After Wrenn is injured on her bike by Letitia's car, Tripp offers her to recuperate at his mansion. While there she manages to make some new friends, and makes others suspicious. Lisa and Nick have a fight over Nick. Meanwhile, Nola Lyons, the new chief of staff impresses Patrick by being aggressive, but others are not. Brian is surprised to learn that Andrea is refusing to fight her cancer through a medical trial.
Nick is sent in to work his magic on Karen while she prepares for her fifth wedding, this time to Simon Elder which doesn't sit well with others. Meanwhile, despite Nola advising against it, Patrick hires Jeremy to his team; Brian finds himself growing closer to Andrea as she lays in bed getting sicker; and Letitia believes someone has overstayed their welcome.
Patrick invites Carmelita to his inauguration despite warnings not to do so. Meanwhile, Chase threatens to go public; Simon blackmails his younger brother; and Karen is mugged.
The Darlings must deal with the aftermath following the inauguration, which leaves one person dead, one shot, and one with amensia. Meanwhile, Nick and Lisa discuss custody arrangements for their daughter.
The Darlings go away, a reporter begins to dig into the truth regarding the rumors surrounding the family, and finds a chauffeur willing to talk. Meanwhile, the fashion show is held at the Darling mansion where one socialite confronts the Darling matriarch.
Lisa takes Kiki out of town and Nick takes the Darlings' jet to go after them, but he has a surprise when Brian and Karen decide to go along for their own reasons.
Karen and Nick profess their love for each other, and she reveals to him that she is pregnant with Simon's baby. Simon and Tripp plan to celebrate their new partnership and go public with their bio-fuel patent, with a party at the Darling mansion. Elsewhere, Simon chooses Jeremy to pull off his fake murder, but Nola believes he is being set up in a trap. She wants to save her bother, but fears Jeremy will be hurt by Simon. Meanwhile, Andrea learns of Brian's plans to cheat on her with his ex-wife and throws him out of the Imperial, forcing Brian to shack up with Nick. And Patrick meets again with with Congressman Whatley who hit on him, but this time it's Dana, the congressman's wife who is making moves on Patrick.
Simon's stab wounds are healing and Nick discovers how Nola has been controlled by Simon. Meanwhile, begins penning a tell all book about the Darlings, and Nola heads to China in hopes of rescuing her brother.