"Oleanna" is a short three-act play surrounding the consequences of miscommunication between a male college professor and his impressionable female student.

In Act One, Carol drops by her John's office, her professor. She is looking for guidance, as she is failing the class and is desperate to do better. When the curtain rises, John is on the phone with his wife Grace arguing about the house they are buying now that John has been offered tenure. John cuts the conversation short so he can address Carol, who sits across from him listening to the entire conversation. Now that she has John's attention, Carol complains that no matter what she does in John's class, she can't seem to get ahead. She's doing everything John has asked her to: she bought and read John's book, she shows up for class, she takes notes, but there's something in the language that she can't quite get a handle on. When it's clear that John doesn't have time to engage in a long conversation with Carol, John tries to dismiss her but Carol breaks down into tears berating herself as stupid. John attempts to console Carol by speaking plainly to her, dropping all pretense of the professor-student relationship. When Carol composes herself, she asks why John has put aside his important meetings to speak with her. He answers, "because I like you."

John's casual conversation continues as he benevolently offers Carol an "A" for her work thus far. He says she can start the course over and that grades don't matter. What matters to John is awakening her curiosity about the subject. He says that as long as she comes for regular meetings in his office to discuss class themes, he'll give her an "A." Throughout their meeting, Carol keeps careful notes of everything John says even though he urges her to put the notebook away. Their conversation continues with Carol growing increasingly more upset as John uses words she can't understand. She is so frustrated that she begins screaming and crying. To comfort her, John stands up and puts his arm around her, but she backs away and shouts "NO!" Soon after, John rushes out of his office to meet his family for a surprise birthday party.

Act Two begins with another meeting in John's office. Since leaving the first meeting, Carol has joined a support group that convinces her John sexually harassed her during the last meeting. She has brought up a formal complaint against him and delivered it to the tenure committee who are now holding a meeting to discuss whether or not John should be granted tenure. John has called Carol to the office to discuss the miscommunication and misconceptions of their last meetings. He seems sure that the tenure committee will dismiss her claims, and he would like to protect Carol before their decision affects her future. Carol's attitude from Act One has completely changed: she is more confident, realizing that she now holds power over John's future. Even though she admits the accusations might have been fabricated, John cannot deny that they occurred. He did put his arm around her and suggest private meetings in his office in exchange for an "A." Even though it could be argued that Carol has taken John's comments out of context, he cannot deny that they were ever said.

Carol's anger comes not from John's treatment of her, but from his seemingly elitist, flippant treatment of higher education. During their initial meeting, John compared college education to hazing and insulted the tenure committee. In Carol's mind, John's sins are sins against the entire student body, a bold display of the power struggle in academia: professors have all the powers while students are forced to follow their self-aggrandizing rules. In the report, Carol has accused John of being sexist and elitist. Towards the end of their conversation, John urges Carol to see him as a human being, not as a symbol for something larger: he has a family, a home, responsibilities, and a real love for his job. No matter what he argues, Carol refuses to be swayed. She wants to follow the rules set forth by the university and for the proper authorities to handle John's case. She stands to leave and John begs her to sit back down and finish their conversation. She refuses to listen, so John grabs her arm, which causes Carol to desperately shriek and scream for help as if she's being abused. Rather than fight back against John's physical restrain, Carol immediately shouts for others to help her.

In Act Three, John has realized that the tenure committee found some validity to Carol's complaint and has suggested disciplinary action in addition to retracting his tenure offer. Not only is John losing his house due to Carol's complaints, he also stands to lose his job. John is desperate for Carol to retract her complaints and admit that she misconstrued the events of their first meeting. He attempts to apologize for his contribution to their conflict, but Carol balks at his apology by saying that he doesn't fully understand the consequences of his actions. In her mind, John has tried to rape her - both physically and academically. She questions John's true belief in free-thought: if he believes that everyone should make up their own minds on issues, why is he questioning the tenure committee's decision to suspend him. Don't they have the right to free thought as well? In a role reversal from Act One, Carol is now controlling and condescending while John is pleading and desperate.

As their final conversation comes to a close, Carol presents her requirements if John would like her to drop her case. She would like him to support the removal of many academic texts, including the book John wrote himself, from the school library. This suggestion goes directly against John's view of free-thought and free-speech favoring Carol's extreme conservative agenda. This request causes something to snap in John's mind, and he suddenly doesn't care if he loses his job. He must stand up for what he believes in. He must fight against bullies and censors like Carol. He demands that she leave his office but before she goes, Carol chides John for calling his wife "baby." This comment steps totally over the line as Carol is no longer judging John's academic life but his personal life as well. He grabs Carol and begins beating her, shouting that he would never rape her - he wouldn't even touch her with a ten-foot pole - and that she has no right to comment on his marriage. He raises a chair above his head and threatens to throw it at Carol and calls her a "cunt." Carol collapses on the floor and repeats to herself "Yes. That's right ... that's right."