While on leave in Hawaii, fighter pilot Chandler Williams has a torrid affair. He asks the woman, Heather, to come away with him, but she never shows up. Two months later, he returns home for his father's wedding. He is shocked to discover that Richard is marrying Heather, but keeps the truth a secret in the interest of his father's happiness. Chandler elects to join the family company. He flirts with longtime friend Samantha Sanchez, his father's assistant. Chandler's brother Peter tells Samantha that she isn't good enough for Chandler, and then makes a move on her. Richard confesses that he and Heather have yet to sleep together. Peter suspects that Heather tricked Richard into tearing up a prenuptial agreement. Richard angers Heather by inviting his ex-wife Gwen to the wedding. Heather tells Samantha that her services are no longer required. Samantha overhears Heather manipulating Richard into asking Gwen to move elsewhere. Samantha warns Gwen, who swears that no one will force

Heather shares her plans for the baby with Chandler. She will tell Richard that she got pregnant on their honeymoon, and pretend that it is his child. Peter is furious that Heather will soon assume control of Dress2K, an internet company in which the corporation invested millions. While Richard and Heather are away on their honeymoon, he organizes an emergency meeting and tries to kill the deal. He cannot do this without unanimous support, and Chandler opposes him. He insists that, for his father's sake, they must give Heather the benefit of the doubt. Peter and Chandler come to blows when a workout gets out of hand. Peter pleads with Gwen to lobby Chandler on his behalf. She sends Samantha, who loses her resolve after Chandler speaks of his loyalty to his father. Peter has no choice but to sign off on the deal. While in Hawaii, Heather is overcome with thoughts of Chandler. Her phone call interrupts a kiss between Chandler and Samantha. She convinces Richard to cut their honeymoon sho

Peter still hopes to scuttle the Dress2K deal, but Richard and Heather return unexpectedly. Richard scolds Chandler for not telling him of Peter's betrayal. Heather unsuccessfully tries to put the moves on Peter. Samantha is appointed second-in-command of Dress2K. She actually likes Heather's ideas, and recommends throwing a Thursday dinner party (a Williams family tradition) to hit up the others for more money. Chandler and Samantha admit their feelings for each other. Heather spies them kissing in the garden. Laurie warns David about Jenny's drinking problem. Peter realizes the real reason for Heather's dinner party (thanks to her use of the worst segue in recorded history), and insults her. She throws a drink in his face. Jenny slips out in search of a drink, but David angrily confronts her and knocks her glass to the floor. She is surprised to find David at her AA meeting the next morning. He has been sober for seven years, but found himself tempted at the party. Ethan Benchley, th

Chandler refuses to sleep with Heather, but breaks things off with Samantha. Heather faints during a Dress2K fashion show. Chandler insists that she must take better care of herself, and flies her to San Diego for a doctor's appointment. Chandler threatens to tell Richard about Heather's pregnancy unless she does it herself. She instead asks Richard about starting a family. He turns her down. Peter convinces Samantha to pose as his fiancée to help land a client. She goes out with him the following night and has a good time, until Peter tries to kiss her. Peter helps her get a promotion, and insists that he has changed his ways. After Heather mocks him, he expresses suspicion about her relationship with Chandler. David pushes Jenny away because he believes it is dangerous for alcoholics to get involved. Laurie begins to realize her feelings for David, only to catch him kissing Jenny. Gwen encourages Ethan to apply to an exclusive prep school.

Heather is furious when Richard approves renovations on Gwen's hotels instead of giving more money to Dress2K. Chandler considers escaping his problems by returning to the Navy, but Richard angrily dissuades him. Peter spies Chandler and Heather in the midst of an intense conversation. Through a series of very fortunate circumstances, he learns that Heather may have visited a Hawaiian hotel around the same time that Chandler had a fling with a young brunette at the same establishment. He hacks into the hotel computer and obtains surveillance camera footage of Chandler and Heather having an elevator tryst. Peter blackmails Heather into turning over control of Dress2K to him. He quells Samantha's suspicions by putting her in charge of the company. A guilt-ridden Chandler decides to confess the affair to his father. He and Peter burst into Richard's bedroom to find that he has collapsed with a heart attack while having sex with Heather. Jenny decides to become more involved with the club,

Richard dies of a heart attack. The family suspects foul play, but Heather denies any wrongdoing. Chandler tells Heather that he will help with the baby, but rejects her advances. Jack returns from Europe to become CEO of Williams Enterprises, as Richard had stipulated in his will. Heather is not mentioned in the will. Peter, using the blackmail tape as leverage, pays Heather one million dollars to leave town quietly. On her way out of the mansion, she meets a lawyer, who tells her that Richard revised the will during his honeymoon. Heather receives an equal share of Richard's fortune. Jack angrily refutes Peter's attempt to show him the tape of Chandler and Heather. He turns to his mother instead. Gwen threatens Heather, who smugly announces that she is carrying Richard's child. Jenny shows up drunk for her father's funeral. Laurie accuses her of selfishness, as she always needs everyone's attention. A hurt Jenny moves in with David.

A businessman makes Jack a substantial offer for the company. Even after Chandler punches out Peter in the conference room, Jack decides to keep the company for the good of the family. Chandler plans to leave town after his affair with Heather becomes public. He changes his mind after Scott shows him plans for a plane prototype that had been his father's dream. Chandler lies to Gwen about the paternity of Heather's baby. After Heather convinces Jack to approve Richard's project, a grateful Chandler makes out with her. Jack interrupts and urges Chandler to stay away from Heather. Samantha begins falling for Peter after a business trip to San Francisco. Heather tells her about Peter's blackmail scheme and warns that he is using her. Samantha rejects Peter, who insists that he really cares for her. Jenny becomes addicted to pain pills. David encourages her to move back home. David calls Laurie to the house secretly to discuss Jenny's problems. Jenny sees them in an embrace. Ethan spies on

Heather complains about being shut out of board meetings. She decides to spend all of her time making passes at Chandler. Jack tries to keep her busy by asking her to co-coordinate a hospital fundraiser. Heather meets a doctor and begins dating him to make Chandler jealous. She checks into a motel and tricks Chandler into believing that she is spending the night with the doctor. He shows up in a rage, only to find that she is alone. He realizes that he has been set up and declares that he wants nothing to do with Heather. As he drives off, Heather chases after him and falls down the stairs. Jenny accuses Laurie and David of having an affair. Jack orders her to check into rehab, and Jenny blames Laurie. Jenny convinces Jack to leave her alone at the center. She runs off to a bar and gets hammered. David and Laurie find her passed out in the hallway outside his apartment. They take care of her, but David confesses to Laurie that he doesn't love Jenny. David and Laurie admit their attract

Heather loses the baby. Gwen tries to provide comfort, but clashes with her after Heather remarks that the miscarriage was probably best for the family. A sobbing Heather shows up at a board meeting and convinces Jack to let her share the reins of Dress2K with Samantha. Chandler accuses her of using the loss of the baby as part of a scheme. Chandler and Heather later grieve for their child after trying to save an injured dog. Gwen is furious when Jack withdraws funding for her hotel renovations. He then tries to sell the flagship hotel, the Beverly, to Margo Dupree, the pretentious owner of a large chain. Margo backs out of the deal after Gwen throws her out of the Beverly. Jack softens and decides to inject more cash into the hotels. Peter takes Samantha to an observation point, where he watches a woman and baby. He claims that the woman was his fiancée, whom he left because Richard threatened to disinherit him. He tearfully states that this is why he cannot open up to anyone. Samanth

Samantha and Heather get into a slap fight after Heather appears on a magazine cover as the ""savior of Dress2K."" Chandler and Scott are enraged when their budget gets slashed in half. Heather discovers Peter's affair with Samantha. Chandler's comments about Peter's playboy past prompt Heather to suspect that the story about Maureen is phony. She pays Maureen $10,000 for the truth. She threatens to tell Samantha unless Peter has her restored as head of Dress2K. Peter convinces Jack to help him out. Jack promotes Heather, explaining that she is willing to shift funds from Dress2K to the aviation department to provide the necessary funding. Samantha quits, but Peter persuades her to come back and help him plot against Heather. Chandler and Heather discuss the possibility of a relationship. Chandler creates a stir by asking Heather to dance at a company function. Jenny pushes for a promotion for David, and freaks him out by discussing their long-term plans as a couple. Jack notices Laurie'

David saves Jenny from drowning. Jenny does not reveal what she saw at David's apartment. She instead lays a guilt trip on David and Laurie to keep him tied to her. Jack orders David to stay with Jenny, as he believes that she will otherwise self-destruct. A drunken Laurie laments the fact that Jenny is a total loser, but always gets her way. She slaps David in the middle of the club. Heather threatens to expose Peter's secret unless he finds a way to control Samantha. Despite his pleas, Samantha begins bugging Heather's office. Heather embezzles over four million dollars from the Williams Foundation's charity fund to pay for a super computer for Chandler's project, the flying wing. Samantha goes to Chandler with the information. Peter realizes that Samantha recorded a conversation in which he and Heather discussed the ruse involving Maureen. Claiming that he is worried that Samantha could be jailed for her actions, he destroys the tape before she can listen to it. He also advises her

Gwen and Jack disagree about how to handle the situation after word of Heather's embezzlement gets out. Gwen has Heather arrested in the middle of a party, but she is quickly released. Heather begins suffering nightmares about her childhood. Gwen is furious to see Jack consoling her. Samantha refuses to move in with Peter because it goes against her religious beliefs. He eventually proposes, but Maureen reappears with more blackmail demands. Jenny tries to keep Laurie away from David by setting her up with someone else. Gwen tells them that she is tired of serving as their referee. Ethan catches Faith kissing another guy. Scott becomes attracted to a woman who works for the aviation division's chief competitor. He fears that she stole information from him.

Peter pays off Maureen, but warns her to stay away for good. Peter and Samantha travel to her grandfather's winery to ask for his blessing. He doesn't feel that Peter is the right man for her. Peter angrily leaves and says the relationship is over. Samantha later has a change of heart and returns home. She tells Peter that she loves him, and will marry him in spite of her grandfather's objections. Maureen ignores Peter's threat and continues to cause trouble. After an encounter with a high school classmate, Heather admits to Chandler that she has been lying about her past. She had to change her name to escape an abusive stepfather. Heather continues to have nightmares, and is terrified when she receives a phone call from the man stalking her in the dreams. Jack and Gwen sleep together, but Gwen considers their night together a mistake. Heather tries to pry into their business and spread gossip. Faith dumps Ethan in favor of her other boyfriend. Ethan wins her back by follo