Once Upon a Lie Book Club Questions
by Max Monroe
These questions assume everyone has finished the book and contain spoilers, including the ending.
This novel gives book clubs plenty to argue about: trust, surveillance, family loyalty, and whether love can survive a foundation built on deception. The questions below are designed to move your group from gut reactions about the characters to deeper conversation about the choices driving the plot.
Pick a few questions that fit your time, or work through them in order. You do not need to agree on every answer. Let the tense moments and messy relationships spark honest discussion, and feel free to bring in your own favorite scenes.
Trust, Lies, and Undercover Lines
- 1.Shane is assigned to go undercover as a disgraced cop and get close to Valentina, while Mike warns him not to mistake innocence for ignorance. Did you believe Valentina was unwitting, or did the novel keep you suspecting The Hole Story was part of Tommy's money laundering?
- 2.Shane searches Valentina's trash, photographs her financial documents while she sleeps, and lets her believe he was helping a friend move when he met Mike. Which of his deceptions felt most damaging, and did the novel do enough to make his love for Teeny feel genuine rather than convenient?
- 3.Shane leaps from his balcony to save Valentina when Ken Fortune's helicopter drops an AC unit into her condo, then later cares for her through a panic attack. How does this rescue change their relationship, and is it troubling that so much intimacy grows while Shane is hiding his real identity?
- 4.At Honky Tonk Parade, James and Crew reveal that Shane knows Dom and has been evasive about his firing, prompting Valentina to leave the bar. Was Valentina's reaction fair, and should Shane have told her more at her door instead of asking for time?
Family Pressure and Protection
- 5.Valentina confronts Shane at the Cordone Freight charity gala, tries to punch him, slaps him, and then is shielded by him when gunfire breaks out. How does this scene set up the novel's tension between betrayal and protection, and did it make you more sympathetic to either character?
- 6.Nico forces Shane at gunpoint in the men's bathroom to text Valentina that he is leaving and never coming back, then smashes Shane's phone. Did you see Nico's actions as protecting his sister or as another form of Cordone family control, and did you agree with his choice?
- 7.Tommy Cordone pushes Valentina toward Leonidas, demands her quarterly tax paperwork on short notice, and sends Leo to pick it up. How does the Cordone family pressure shape Valentina's choices, and did she have real agency in her relationship with Shane?
- 8.Alfred Sutter functions as Valentina's found family, counsels her about love, commemorates Avalyn's birthday, and eventually leaves her his house and Pip. What role does Alfred play in Valentina's ideas about romance and happy endings, and did his death feel like a meaningful part of the ending or an unnecessary sadness?
Fairy Tales, Independence, and Public Scrutiny
- 9.The Magnolia Condos HOA rules, Rita Fortune's violation tickets, and the Magnolia Connect chat are played for comedy but also create constant surveillance. How does the building's gossip and rule enforcement mirror Shane's undercover spying on Valentina?
- 10.Valentina says fairy tales are not for girls like her and later wonders whether they start with once upon a lie. How does the novel use fairy-tale language and Alfred and Avalyn's love story to comment on Valentina and Shane's relationship?
- 11.Teeny insists she does not need a man or love and says she will DIY her own fairy tale with bagels and books, yet she later pursues Shane and marries him. Did the ending undermine her independence, or did it show her choosing love on her own terms?
The Gala, Revelations, and the Ending
- 12.Mike reveals that Valentina has been cleared, that Nico is CIA, and that Shane is relieved from undercover duty, but Shane later disobeys orders and goes to the gala. Did you agree with Shane's decision to attend the Cordone Ball, and was the federal operation portrayed as justified or as another group using Valentina?
- 13.During the gala takedown, Nico arrests his own father, Shane takes a bullet for Valentina, and Valentina learns that Shane's assignment involving her was real but that he chose her anyway. Which revelation landed most powerfully for you, and did the reconciliation feel earned after so many lies?
- 14.The novel ends with Shane and Valentina marrying in Avalyn's favorite park, Alfred dying in his sleep, and Shane and Teeny moving into Alfred's house with Pip. Did this ending feel like a satisfying fairy tale, a real love story, or too tidy given the deception and danger that came before?