54 pages • 1 hour read
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Content Warning: This section of the guide includes discussion of graphic violence, mental illness, emotional abuse, and gender discrimination.
Gather initial thoughts and broad opinions about the book.
1. The novel’s central theme is that love is a form of obsession. Did you find this premise compelling or unsettling as you were reading? How did the dark mafia romance setting influence your acceptance of Christian’s and Gianna’s intense dynamic?
2. Danielle Lori is known for her Made series, with each book focusing on a different couple within the same world. For those who have read other books in the series, like The Sweetest Oblivion, how does Christian and Gianna’s story compare? Does it add new layers to the Cosa Nostra world Lori has built?
3. What was the most memorable scene or interaction for you in The Maddest Obsession? What made it stand out against the backdrop of constant tension and violence?
Encourage readers to connect the book’s themes and characters with their personal experiences.
1. Christian uses rigid order and routines to cope with his past, while Gianna embraces chaos as a form of rebellion. Have you ever found yourself leaning toward one of these coping mechanisms during a stressful time? What value or limitations do you see in each approach?
2. Christian and Gianna communicate through games, insults, and power plays rather than direct emotional honesty for much of the book. Have you ever seen people use similar “games” in real-life relationships to protect themselves or to test boundaries?
3. Christian’s protectiveness often manifests as extreme violence, such as killing a man for following Gianna. At what point, if any, did his behavior become irredeemable for you, and why?
4. Does the novel’s suggestion that some people require more intensity in relationships to feel safe or seen ring true for you? What makes a connection feel secure to you?
Examine the book’s relevance to societal issues, historical events, or cultural themes.
1. The story is set within the patriarchal world of the Cosa Nostra, where women are often treated as assets and their marriages are strategic. How does Gianna’s rebellion against this system reflect broader conversations about female agency and autonomy in restrictive environments?
2. The novel grounds its characters’ extreme behaviors in the psychology of trauma. How accurate is the novel’s depiction of trauma and mental illness? Do novels have a responsibility to handle these topics rigorously?
Dive into the book’s structure, characters, themes, and symbolism.
1. The first part of the book uses a nonlinear structure, contrasting Gianna’s year-by-year progression with Christian’s memories during his 2015 therapy sessions. What effect did this narrative choice have on your understanding of Christian’s obsession from the very beginning? How did it shape the story’s tension before their relationship truly began?
2. What is the significance of the number three as a symbol for Christian? How does its meaning evolve from a marker of his rigid control to an echo of his traumatic past after he finally reveals its origin?
3. The recurring motif of darkness is central to the story, with Gianna fearing it and Christian “ruling” it. How does the novel use scenes set in darkness, like the nightclub shootout, to advance their emotional intimacy in a way that couldn’t happen in the light?
4. Gianna’s character arc is tied to the myth of Andromeda. In what specific moments do you see her move from feeling like a sacrificed victim to becoming a “ruler”?
5. How do Dr. Taylor’s therapy sessions function as a framing device for the narrative? Does her professional “diagnosis” that love is “the maddest obsession” successfully legitimize Christian and Gianna’s relationship for you as a reader (292)?
Encourage imaginative and creative connections to the book.
1. Christian’s tattoos, like the Russian prison markings, tell the story of his past. If Gianna were to get a tattoo to symbolize her own journey of survival and reclaiming her power, what do you think it would be, and why?
2. What kind of future do you imagine for Christian, Gianna, and their daughter, Kat? Do you think Christian’s obsessive nature will continue to be a source of strength for their family, or could it become a source of conflict as their daughter grows up?
3. If The Maddest Obsession were adapted into a film or a limited series, whom would you cast as Christian and Gianna? What qualities would the actors need to capture the characters’ intense and complex dynamic?


