When Nick's father mysteriously dies in a plane crash, he agrees to take his position as the Darling family's lawyer, while trying to discover who committed the murder. The Darlings, the richest family in New York, constantly rely on Nick to solve their problems. Nick struggles to balance his morals and family life while dealing with the demands of the Darlings.
Tripp and Letitia Darling throw Nick a luxurious birthday party on a yacht; Jeremy reveals his feelings for Lisa to the mysterious Nola Lyons; Brian is reunited with his illegitimate son; someone is arrested for murder.
The Darlings deal with funeral arrangements and the aftermath of the arrest of a suspect in the murder of Dutch George; Jeremy discovers Nola Lyons' real profession; Lisa and Nick talk about having another child; 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.
As Election Day nears, Patrick insists on taking his relationship with Carmelita public; Ellen's brother, Chase, demands to know the truth about his sister's death; Nick and Lisa go to couples therapy; Brian Jr. goes missing.
Nick faces an uphill battle defending Letitia in the murder case until he discovers a secret about Nola; Karen asks Nick to tell Tripp that she's marrying Simon Elder; Andrea and Brian learn shocking news after a trip to the doctor.
After Letitia hits a pretty, young bicyclist with her car, Tripp invites the woman to recuperate at the Darling mansion; Patrick is delighted with Nola's aggressive manner as his new chief of staff.
As Karen excitedly prepares for her wedding day, she is convinced that this fifth marriage -- to family nemesis Simon Elder -- is the one that will end in happily ever after. But Tripp is still suspicious of Simon's real motives and wants Nick to make one last-ditch effort to keep the wedding from happening. Lisa hopes taking Jeremy to the wedding will make Nick jealous. In other developments, Patrick hires Jeremy to join his senate team, against Nola's protestations; Brian finds himself drawing closer to Andrea as her illness worsens; and when Letitia sees Tripp paying too much attention to their houseguest, Wrenn, she realizes that this pretty, young woman has overstayed her welcome.
Filled with love for Carmelita, newly-elected Senator Patrick Darling goes against Nick and Tripp's advice and invites her to his inauguration. Meanwhile Chase defies his agreement with the Darlings and threatens to go public with his accusation that Patrick murdered his sister; Jeremy finds out that Simon has control of Nola's little brother; as Andrea's health dims, Brian promises God anything to make her well again; and Karen goes to Nick's apartment to make amends with him, but is confronted by a gun-wielding intruder.
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.
Nick declares his true feelings when faced with a life-and-death situation. Meanwhile, still despairing over her fourth marriage failure, Karen drops a bombshell. Then, Patrick receives a shocking proposal.
Simon provides Nola with a solution to her problems. Meanwhile, Karen is faced with an impossible decision regarding Nick, and Patrick finds himself in a compromising position.
Nick finds out his father is alive while Karen loses Simon's baby which she was pregnant with. Nick and Karen finally get together while Jeremy Proposes to Nola who is finally about to find her brother.
Nick searches for his father's killer. When the family has a photo shoot Juliet refuses to be there. Patrick has to deal with his father who wants him to run for the senate.
Nick tries to fix things when the Darlings are blackmailed over a sex tape starring a family member. Patrick is upset over being forced to end things with Carmelita. Brian's wife gets suspicious over the Swedish orphan he brought home. Jeremy tries to keep it quiet about him and Natalie, but when they all show up at a fundraiser for Patrick things get out of control.
Tripp sends Nick to a vineyard in Italy to get information about his father's death. Nick decides to bring Lisa along to spend some time with her away from the Darlings but Freddy and Karen are following them everywhere they go. After Leticia admits she was unfaithful to him, Tripp decides to find out if all of his children are really his.
Nick finds he has a lot in common with Simon, Tripp's nemesis. In a case of sibling rivalry Jeremy and Juliet decide to try and outdo each other for their separate birthday parties. Brian Jr. wants to tell Brian's wife the truth. Karen tries to get Freddy into a fancy country club.
A high stakes poker game pits Simon Elder against Tripp, Karen needs a favor from her irresistible ex husband, and pampered Jeremy gets a real job.
Karen is getting married, but her strong desire for Nick might be more of a distraction then she could have ever thought. Brian Jr.'s mother comes back into town trying to get her son back, but the once arrogant Brian has another idea.
Thanksgiving has arrived and Nick George wants to spend the day with his wife and daughter, but Tripp has another idea. Tripp wants Nick to set up a meeting with Simon Elder so Tripp and Simon can talk face-to-face once and for all. Meanwhile, Letitia helps Karen try and to get closer to Nick. Brian fights to keep his ex-girlfriend, Andrea, from taking his son away from him while Jeremy goes on a first date with Sofia.
This flashback episode reveals secrets about Dutch (Nick's father) and the relationships he had with Nick, Tripp, and Letitia. Karen's intimate view towards Nick is put on hold as she takes a liking to Simon Elder. Brian's attempt to get his son takes a turn he didn't expect and Jeremy continues to hide how much he is worth from Sofia.
Nick learns Simon and Karen are secretly together, but refuses to say why it truly bothers him. Karen doesn't attend the family tradition of watching "The Nutcracker" in order to meet a mysterious person. Brian's suspension from the ministry makes him look elsewhere for a job, and Letitia suggests he go to Tripp for guidance. Meanwhile, Juliet has a visitor from the Seychelles, and Carmelita tells Patrick she thinks she's being watched by someone.