When Cybill was sixteen she wrote a letter as an assignment for English class about her hopes and dreams for the future. Now thirty years later her former teacher has mailed it to her. Cybill's afraid to open it because she thinks it will be too depressing. Meanwhile, Kevin and Rachel return home from their vacation, fighting. Rachel thinks he might be having an affair and goes for a ride on her auto mechanic Buck's bike in retaliation. A drunken Kevin calls Cybill to the trattoria to be his designated driver and reveals the reason for their problems is that he wasn't awarded tenure. Cybill tells him he better tell Rachel before it's too late. When Cybill learns Rachel is still seeing Buck she goes after her. She finds her in front of the Twin Coconuts Motel waffling as to whether or not to have a rendezvous with the mechanic. Cybill stops her. As they leave, they discover a disheveled Sean going into a room. He isn't with Zoey. Cybill wonders what to do with her knowledge. She decides to read her letter, hoping it will raise her spirits. She discovers that the letter wasn't about her hopes and dreams at all, but about her dreams for her boyfriend at the time, Chip Duncan. Later, Sean tells Zoey the truth and she throws him out of the house. Kevin tells Rachel the truth about his problems at work and she reveals what she was almost driven to do. They agree to go for counseling. Maryann is attending a '70's disco charity ball, Hustle for the Homeless, and wants Ira to be her trophy date to get back at Dr. Dick. After mixing her allergy medication and liquor she makes a fool of herself on the dance floor. She ditches Ira at the dance and crawls out on her hands and knees.