The Cherry Orchard and Other Plays
Anton Pavlovich Chekhov
Book Club
The Cherry Orchard and Other Plays
8 ways to start a deeper conversation.
Contains spoilers for the entire book.
Discussion topics
Topic 01 of 08
To Moscow
In The Three Sisters, Olga, Masha and Irina keep telling each other that they will go back to Moscow: what does Moscow stand for in their lives?
Keep the conversation going
- Why do they never go?
- Is their longing what keeps them going, or what keeps them stuck?
There is no single right answer. Bring your own reading.
Discussion topics
In The Three Sisters, Olga, Masha and Irina keep telling each other that they will go back to Moscow: what does Moscow stand for in their lives?
Keep the conversation going
- Why do they never go?
- Is their longing what keeps them going, or what keeps them stuck?
How does Natasha, Andrey’s fiancée in Act I, come to rule the Prosorov house by the end?
Keep the conversation going
- How much is Andrey to blame for what happens to his sisters?
- What did Natasha’s treatment of old Anfisa tell you about her?
Irina dreams of a life of work, but finds her job at the telegraph office empty: what does the play say about work as an answer to unhappiness?
Keep the conversation going
- Do Vershinin and Tuzenbach believe their own talk of how beautiful life will be in two or three hundred years?
- Is that hope for the future a comfort to the characters, or an excuse?
Why can Madame Ranevsky and Gaev not bring themselves to accept Lopakhin’s plan to save the estate by cutting the orchard down?
Keep the conversation going
- Is their attachment to the orchard beautiful, foolish or both?
- What does the orchard mean to each of the main characters?
How did you respond to Lopakhin’s speech in Act III, when the son of a serf announces that he has bought the estate his family once served?
Keep the conversation going
- Is Lopakhin the villain of the play, its hero, or neither?
- Why do you think he never proposes to Varya?
What future does Trofimov promise Anya, and how far do you trust him to bring it about?
Keep the conversation going
- Does Chekhov treat the eternal student with sympathy, with irony or with both?
- How do the young people’s hopes sit beside the older generation’s grief?
Chekhov called The Cherry Orchard a comedy: where did you find it funny?
Keep the conversation going
- What do characters like Epikhodov and Charlotta add to a play about losing a home?
- Does the last scene, with old Fiers forgotten in the locked house, change your answer?
The Proposal and The Bear both turn quarrels into engagements: what makes these farces still funny more than a century later?
Keep the conversation going
- How does the darker On the High Road differ from them in tone?
- Which themes of the full-length plays did you find here in miniature?
There is no single right answer. Bring your own reading.

