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 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