Martin, while putting away Jeremy's laundry, comes across an adult magazine and a joint. Martin informs Judith, and they agree that Martin will have a talk with Jeremy. Jeremy agrees to not smoke pot, and Martin admits that he used to smoke pot a long time ago. After Martin discusses the matter with Eddie on the basketball court, they return to Martin's apartment. Eddie spots the joint and lights up. Martin joins him.

Martin's new girlfriend of three weeks, Charlotte, has a porn star past. Martin learns from Eddie. Charlotte reveals that her biggest secret is that she cannot drive. Martin begs to differ, and Charlotte admits to appearing in six porn videos to pay for college and is not ashamed. Martin and Charlotte try to continue their relationship despite this conflict. Martin tries to continue dating Charlotte, even though he keeps seeing her in porn star roles and settings.

When Richard misses his and Judith's second anniversary, she confides to Martin that all is not well in their marriage.

Martin is disgusted by the quality of the books Gibby is forcing him to edit, and his lack of appreciation. Meanwhile, Eddie is fired from his talk show and his wife Jeanette leaves him on the same day. Eddie begins to reassess his life and Martin encourages him to make a change, proposing they collaborate on creating an up market magazine.

Susan (Martin's sister) plans a wedding.

Martin tries to cheer Toby up when her cat dies by buying her a replacement. When she refuses the gift, he has to keep the pet himself.