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,