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Patrick tells his father he doesn't want to run for Senate just as a photo shoot, with lions, is organised to promote the family. Nick finds out from Tish that his father and her had an affair for many years. Karen wants Nick to tell Freddy he cannot be in the photo shoot. Nick and Lisa take in Brian's illegitimate son Brian Jr. temporarily. Nick meets airplane mechanic Norman Exley and finds that Norman was blackmailing Brian about his illegitimate son. Juliet discovers that the reason she cannot get to stay in the penthouse suite is because her ex-best friend Natalie is staying there and Jeremy is involved with her, unknown to Juliet. Nick, through the help of Trip, eventually finds out the combination of his father's briefcase and finds information about an unknown man, Simon Elder.
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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 fianc? Freddie's caddy's, in a compromising position. Meanwhile, Patrick has a panic attack over running for Senate and is advised to give up seeing Carmelita. Elsewhere, Juliet and Natalie fight on the red carpet at Patrick's event.
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Nick sees references in his dad's diary to meetings with a man named "C". Nick and Lisa go to Italy to try and 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 Freddie find out about their trip and tag along. Karen lets slip to Lisa that Nick proposed to Karen when they were both 19. The P.I. Harold Templeton tells Nick that his dad asked him to dig up details on Simon Elder and 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 license plate on the car has one initial "C".
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Twins Juliet and Jeremy's 25th birthday party is approaching and their inheritance of 25 million dollars 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 Karen is going to 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 twins 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.
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Carmelita begs Patrick to stop hiding her away from the public and when he does let them be seen in public together photographers take shots of them together which infuriates Patrick. 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 too but he refuses. When Karen and Freddie get to City Hall the clerk tells her she is still married to her third husband, Sebastian. Carmelita finds out that it was Tripp that hired the photographers and refuses his cashiers check to stay out of Patrick's life. Elsewhere, a high-stakes poker game pits Simon Elder against Tripp and ends up with Elder winning Darling Plaza off Tripp. Jeremy gets a real job working as a parking valet at Tripp Industries where he meets the glamorous Sofia.
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Karen is having second thoughts about her wedding to Freddy. Brian Jr's mother Andrea comes back from Brazil and wants to see Brian Jr. 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 is not going to work out. Juliet and Natalie become friends again. Patrick tells Ellen about Carmelita. Tripp learns that Patrick & Ellen are moving into a townhouse in Simon Elder's building. Tripp tells Nick he wants Simon Elder destroyed.
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Nick, Lisa and Kiki arrange to spend Thankgiving together but Tripp has other ideas - he 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 to go to her mothers house after Tish tells her Nick and Karen kissed at the wedding. Ellen shoots Patrick in the leg after finding out that he went to visit Carmelita.
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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 this 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, and then Brian, that Brian is Nick's brother. Jeremy continues to deceive Sofia and pretends to be an artist, with the help of Lisa. Brian Jr. and Andrea move to Brazil and Brian is cut up about losing him.
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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 following 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 it causes her to leave him. Clark calls Patrick to tell him that Carmelita has gone. Nick and Lisa decide to try for another baby and Karen meets her father to assure her father that she is not getting emotionally involved with Simon Elder and that things are going as planned.
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Lisa "kidnaps" Kiki when it is Nick's weekend with her, and takes her to another country. Nick wants Tripp's private jet to get Kiki back, and Tripp agrees. Karen and Brian accompany Nick on his journey. Karen goes on the trip because she hears that there is a very good fertility clinic there. She wants to get sperm, so that she can have a baby. Along the way, the plane encounters some serious turbulence, and Karen gets scared and is convinced that the plane is going to crash. She tells Nick that he is the man for her, and she loves him, and then kisses him. Nick returns the favor, and tells Karen that he loves her. Nick then agrees that he will donate sperm to her, the old-fashioned way. They then land unharmed on ground, and Nick continues on his quest to find Kiki.
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Patrick makes a business deal with Congressman Skip Whatley, then is convinced that he is attracted to him. Karen goes to get an abortion, but couldn't go through with it and Simon spots her leaving the clinic. Andrea finds a condom in Brian's suitcase after he returned with Karen and Nick, and throws him out of his house (Brian went on the trip to have sex with Mei-Ling, his ex-wife, but then backs out - so he got kicked out for no reason). Karen is forced to tell Nick about the pregnancy with Simon's baby, but Nick tells her that he still loves her. Their is a party at the Darling's house, and Simon threatens Karen that she can't do anything to stop him coming near her or the baby - ever. Simon finds out about his baby, and decides to have Jeremy not kill him. Nola was happy that Simon was going to kill himself, because only then would he reveal where Nola's brother is. Nola now starts freaking out when Jeremy tells her that Simon is not going to die, and says that she is still going to kill him, and Jeremy decides to follows her plan...
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Nick finds out that Lisa has decided to write a 'tell-all' unauthorized book on the Darlings. Nola stabs Simon Elder with a letter opener, finally getting the information as to the whereabouts of her kidnapped brother. She decides not to go back to New York. Jeremy proposes to her hoping that she will stay but to no avail. But he moves on pretty quickly, going to Vegas with Simon's nurse and ends up marrying her. Karen and Nick agree to see each other, but after Karen sees Nick with Lisa she falls down stairs and ends up miscarrying Simon's baby. Patrick begins to fall for Congressman Whatley's wife, Dana, but is warned off her by the Congressman. Elsewhere, Brian takes it upon himself to re-decorate Nick's apartment to the intense disapproval of Nick. Nick finds out from Simon that it was his father behind all of Simon's deeds and that he is very much alive.
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