Theo is nervous about his first parent/counselor meetings and student art exhibit. Cliff and family go to the exhibit. Rudy is smitten by one of Theo's students and Theo is smitten by a single mother of a student.
Rudy wants to see a rapper that is performing at a club for older teens. Rudy and her friends lie to their parents in order to get out that evening. When Cliff & Clair find out, they ask Pam to go to the club to keep an eye on Rudy.
Cliff is a chaperon for Olivia's field trip to a museum and he is not looking forward to it. Theo has a fund-raiser plan for the community center - selling silk screened t-shirts. But the t-shirts are not what he expected.
At the community center, Clair gives a legal clinic and Cliff gives a Men's Only clinic. Cliff's clinic teaches etiquette, getting a job, and more. His job session becomes more about being a responsible parent and preventing pregnancies.
Cliff & Clair plan a day at home alone, but Vanessa returns from college for the weekend, then her fiancé comes to find Vanessa. Rudy's friend Kenny comes to visit Rudy. They all talk to Cliff & Clair about their relationship issues.
Cliff builds a room just for Clair, her own special place for work and retreat. Everyone, except Cliff, is upset that she wants to be alone and not spend time with them. Cliff tries to explain the purpose of a special room.
Theo attends a corporate mixer for The Tartan Company, a leading soup manufacturer who boasts that they're "not just soup anymore." His views on how the company should present its image impress the bosses so much that he is offered a job interview in San Francisco.
Pam starts working as an assistant for Cliff. Cliff deals with an impatient pregnant patient who tends to misinterpret the instructions he gives her. Meanwhile, Kenny tries to make Rudy jealous by pretending he is dating someone.
Clair goes away for the weekend and tells Cliff he has to behave and not eat a lot of food that is not on his diet. No one believes he will stick to his diet. Rudy and her friends want to take the subway to a dance.
Olivia's school project is to write about an adult when they were a child, and she writes about Cliff. Theo turns down a corporate job in California so he can finish graduate school in New York. One of Theo's students finds $600.
Willie Colón and Mario Bauzá, legendary Salsa and Latin music performers, play themselves to perform a concert on a local radio station. Clair, who represents them, and Cliff, a big-time fan, go to the station to watch the performance.
As tax day approaches, Cliff tries to get deductions for extended family members, but Claire rebuffs him. Meanwhile, Kenny organizes a surprise birthday party for his girlfriend Deirdre because he's ashamed that he only bought her socks as a gift.