Episode list

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. Eldest daughter Laurie orders her sister Jenny's boyfriend, Billy, to stay away from her. A drunken Jenny smashes up Billy's car after discovering that he is married.

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. 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. While in Hawaii, Heather is overcome with thoughts of Chandler. Her phone call interrupts a kiss between Chandler and Samantha. Jack shows up for the wedding reception. David O'Connor, a man recommended by Jack, arrives to help the girls run their club. He gets off to a bad start with Laurie, but impresses Jenny. Laurie warns David not to get involved with Jenny.

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. Laurie warns David about Jenny's drinking problem. Ethan Benchley, the teenage son of Gwen's late sister, is transferred to her custody after his father abandons him. Gwen has a difficult time convincing him to stay.

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. Peter convinces Samantha to pose as his fiancée to help land a client. 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. Jenny decides to become more involved with the club, Pulse. She turns to alcohol to get through a presentation. Ethan catches Jenny swiping booze, but promises to keep her secret. Laurie draws closer to David after she accompanies him to a play as a favor to Jenny.

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. After Heather convinces Jack to approve Richard's project, a grateful Chandler makes out with her. Samantha begins falling for Peter after a business trip to San Francisco. Jenny becomes addicted to pain pills. David calls Laurie to the house secretly to discuss Jenny's problems. Ethan spies on a teenage neighbour through his telescope.

Heather complains about being shut out of board meetings. 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. Jenny accuses Laurie and David of having an affair. Jack orders her to check into rehab, and Jenny blames Laurie. Jack asks Peter to hit up a client for financing on Chandler's aviation project. Peter gets arrested in a brawl at a strip club after trying to liberate one of the dancers. Bored with her life, Faith latches onto Ethan because she considers him a "bad boy." She convinces him to take Gwen's car to a club, and tries to teach him to kiss.

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. Gwen is furious when Jack withdraws funding for her hotel renovations. 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. Jenny begins doing cocaine. Gwen catches her searching for drugs. Laurie is stung when David continues to sleep with Jenny. Faith accompanies Ethan to Chandler's birthday party at Pulse. She ditches him to flirt with a musician twice her age.

Samantha and Heather get into a slap fight after Heather appears on a magazine cover as the "saviour 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. Jenny pushes for a promotion for David, and freaks him out by discussing their long-term plans as a couple. Jack notices Laurie's sullen mood and issues a warning to David. Gwen catches Faith going through her purse. She realizes that Faith is a manipulative nuisance and bars her from seeing Ethan. Faith shows up at the house and invites the entire school over for a party. She and Ethan sneak off to his room.

David saves Jenny from drowning. 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. 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. Faith convinces a grounded Ethan to sneak off to a sleazy motel with her.