Assistant to the Villain

Content Warning: This section of the guide contains discussion of gender discrimination, physical abuse, emotional abuse, and graphic violence.

Gather initial thoughts and broad opinions about the book.

1. Maehrer subverts traditional fairy-tale tropes by making her villain sympathetic and her “good” characters morally ambiguous. How effective did you find this role reversal, and did it change your perspective on classic fairy tales you may have grown up with?

2. The novel began as a series of TikTok shorts before evolving into a full book. In what ways do you think this social media origin influenced the pacing, style, or character development? For those familiar with Apprentice to the Villain, Maehrer’s sequel, how does the TikTok influence compare between the two works?

3. By the end of the novel, Evie declares she’ll “save The Villain…Or become one trying” (339). What emotional response did this closing line evoke, and what expectations did it set for your understanding of Evie’s character development?

Encourage readers to connect the book’s themes and characters with their personal experiences.

1. Evie initially measures her self-worth by how useful she can be to others, stating she is “addicted to feeling useful. Without it, what value did she hold?” (91). Have you ever fallen into a similar pattern in your relationships, and what helped you recognize your intrinsic value?

2. Throughout the novel, Trystan struggles with the villainous identity that has been forced upon him, feeling that he must live up to his label. When have you felt pigeonholed by others’ expectations or labels, and how did this experience shape your sense of self?

3. Evie discovers that working for the notorious “Villain” provides her with more respect and better treatment than she received in her previous “respectable” employment with the blacksmith. When has a situation in your life completely upended your expectations in a similar way?

4. Trust forms the foundation of Evie and Trystan’s evolving relationship, despite all the reasons they should distrust each other. Which relationship in your life has taught you the most about the importance of trust, and what lesson did you learn?

5. Tatianna deliberately wears pink as a way to control what people notice about her first, reclaiming her identity beyond her healing abilities. What conscious choices do you make about your appearance or behavior to influence others’ perceptions of you?

Explore broader implications and cultural relevance.

1. The novel portrays a society that unquestioningly accepts the king’s narrative about the Villain without seeking evidence, as shown when the village woman cannot name his specific crimes. How does this aspect of the story reflect the way propaganda and misinformation function in our current information landscape?

2. Gender expectations play a subtle role in the novel, particularly in how the blacksmith treats Evie and expects her compliance. How do these power dynamics mirror the challenges women continue to face in professional settings today?

3. In the story, those in positions of power manipulate public perception for their own gain, with the king portraying Trystan as monstrous to unite people against a common enemy. What historical or contemporary examples demonstrate similar tactics, and what are the societal consequences of such manipulation?

Examine technical and thematic elements.

1. The enchanted dagger that wounded Evie becomes a symbol of her unprocessed trauma, with the pain intensifying whenever she confronts its source. How does this physical manifestation enhance the novel’s exploration of psychological wounds, and what significance does it hold when Evie ultimately uses the dagger to kill her abuser?

2. How does Maehrer use the mundane workplace setting and office dynamics to both humanize Trystan and add humor to what might otherwise be a conventional dark fantasy? How does this approach compare to the workplace fantasy elements in books like The House in the Cerulean Sea by TJ Klune?

3. The novel explores multiple definitions of evil through its characters. How do the contrasting figures of Trystan and Evie’s father illustrate different interpretations of villainy, and what statement does this make about the relationship between actions and intentions?

4. Maehrer employs alternating perspectives between Evie and Trystan throughout the novel. How does this narrative choice deepen our understanding of both characters and create tension in their developing relationship?

5. The manor serves simultaneously as a typical villain’s lair, complete with torture chambers and severed heads, and a mundane office space with administrative staff. How does this juxtaposition contribute to the novel’s subversion of fairy-tale tropes?

6. The relationship between Becky and Blade functions as a foil to Evie and Trystan’s romance. What purpose does this secondary relationship serve in the narrative, and how does it highlight specific aspects of the main romance?

Encourage imaginative interaction with the text.

1. What would be your ideal role in Trystan’s office, and which special skill or talent would you contribute to his villainous enterprise?

2. How would you redesign the exaggerated wanted posters of Trystan to more accurately capture his true nature?

3. Which scene from Evie’s potential rescue mission would most effectively showcase her evolution as she embraces her more villainous side?

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