Episode list

After his father Devlin's death in a plane crash, Nick George reluctantly becomes the family lawyer to a clan of New York socialites led by Patrick "Tripp" Darling III.

Just as a photo shoot with lions is organized to promote the family, Patrick tells his father he doesn't want to run for Senate. Nick finds out from Tish that she and his father had a longtime affair. Karen wants Nick to tell Freddy that he cannot be in the photo shoot. Nick and Lisa temporarily take in Brian's illegitimate son Brian Jr. Nick meets airplane mechanic Norman Exley and finds that Norman was blackmailing Brian about his illegitimate son. Juliet discovers that she cannot stay in the penthouse suite because her ex-best friend Natalie is staying there and Jeremy is involved with her. Nick, with Trip's help, eventually finds out the combination of his father's briefcase--and information about an unknown man, Simon Elder.

A sex tape of one of the Darlings is put on the black market and it's Nick's job to find out which of the Darlings made it. They all deny it until a version of it is sent showing Karen and one of her fiancé Freddie's caddies in a compromising position. Patrick has a panic attack over running for Senate and is advised to give up seeing Carmelita. Juliet and Natalie fight on the red carpet at Patrick's event.

Nick sees references in his dad's diary to meetings with a man called "C". Nick and Lisa go to Italy to try to locate a private investigator who did work for Nick's dad and to bring back a special bottle of wine--a Chiavennasca--for Tripp. Karen and Freddy find out about their trip and tag along. Karen lets slip to Lisa that Nick proposed to her when they were 19. P.I. Harold Templeton tells Nick that his dad asked him to dig up details on Simon Elder, then on Tripp. Tripp finds out that one of his children is not his. Juliet finds out about Jeremy's affair with Natalie. Natalie tells Jeremy she is pregnant. Simon Elder approaches Nick as he leaves work and they drive away; the car's license plate has one initial: "C".

Twins Juliet and Jeremy's 25th birthday party is approaching--and their inheritance of $25 million each--but they cannot agree on one thing: Natalie. So they decide to throw separate parties, trying to outdo each other. With their budget going over, Tripp tells Nick to draw up a clause to put a hold on the release of their trust fund until they are 30 years old. Patrick believes that Karen will tell Ellen about Carmelita unless Patrick gets Freddy into his exclusive club. Brian Jr. tells Mei Ling that Brian is his real dad. Mei Ling confronts Brian and asks for a divorce. Neither of the parties goes as planned, leading to Jeremy's trust fund being revoked and him eventually asking Tripp for a job and Juliet asking Tripp to defer her trust fund for another five years.

Carmelita begs Patrick to stop hiding her from the public; when he does let them be seen in public together, photographers take shots of them together, which infuriates him. Nick hears from the airplane accident investigators who tell him it was ruled an accident. Karen asks Nick to go down to City Hall to get her marriage license because she doesn't want to, but he refuses. When Karen and Freddy get to City Hall, the clerk tells her she is still married to her third husband, Sebastian. Carmelita finds out that it was Tripp who hired the photographers and refuses his cashier's check to stay out of Patrick's life. Elsewhere, a high-stakes poker game pits Simon Elder against Tripp and Elder wins Darling Plaza off Tripp. Jeremy gets a real job working as a parking valet at Tripp Industries, where he meets glamorous Sofia.

Karen is having second thoughts about marrying Freddy. Brian Jr.'s mother Andrea returns from Brazil and wants to see him again and take him back to Brazil with her. Lisa refuses to go to the wedding with Nick. Karen eventually marries Freddy but tells Nick and Tish that she wants to divorce him straight away as it's not working out. Juliet and Natalie become friends again. Patrick tells Ellen about Carmelita. Tripp learns that Patrick and Ellen are moving into a townhouse in Simon Elder's building. Tripp tells Nick he wants Simon Elder destroyed.

Nick, Lisa, and Kiki arrange to spend Thanksgiving together but Tripp wants Nick to set up a meet between Simon Elder, Patrick, and himself at their country estate. Lisa goes with Nick and meets Tish and Karen, who are in cahoots to get Nick away from Lisa. Ellen wants to meet Carmelita to set the ground rules about her relationship with Patrick. Jeremy meets Sofia while he's working as a valet but lies to her about who he really is. Lisa leaves for her mother's house after Tish tells her that Nick and Karen kissed at the wedding. Ellen shoots Patrick in the leg after finding out that he went to visit Carmelita.

Brian is arrested after bribing the arbitrator; Tish wants Nick to find a way that will keep him out of jail by any means necessary, but Tripp disagrees, saying that was what got Brian into his current situation. Simon Elder asks Karen to dinner. In flashbacks, Tish tells Nick's dad Dutch that he is the father of one of Tripp's children. Later, she tells Nick, then Brian, that Brian is Nick's brother. With Lisa's help, Jeremy continues to deceive Sofia and pretends to be an artist. Brian Jr. and Andrea move to Brazil and Brian is cut up about losing him.

Because of his illegitimate son and his bribing of a court official, Brian is suspended from the ministry for six months and advised to undergo counseling. He asks Tripp for a job in order to find himself. Simon Elder tells Nick that he is dating Karen and wants to know if he is OK with it. Carmelita calls Patrick to tell him she thinks she's been followed. Kai, a guy Juliet met in the Seychelles, arrives for a two-week stay. Karen meets Simon's ex-wife at dinner; later she attends the annual performance of The Nutcracker at the Tripp residence. Jeremy and Lisa smoke marijuana at the gallery and he makes a pass at her; the next day, the marijuana smell which has permeated a piece of art causes Lisa to get fired. Jeremy finally tells Sofia who he really is but she leaves him; Clark calls Patrick to tell him that Carmelita has gone; Nick and Lisa decide to try for another baby; Karen meets her father to assure him that she is not getting emotionally involved with Simon Elder and that things are going as planned.