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

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,

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

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'