My Favorite Half-Night Stand

Gather initial thoughts and broad opinions about the book.

1. The novel blends the friends-to-lovers romance trope with a modern “catfishing” scenario. Did you find this combination of a classic romance structure with a contemporary digital conflict to be effective? Why or why not?

2. How does My Favorite Half-Night Stand compare to other Christina Lauren books you may have read, like The Unhoneymooners or The Soulmate Equation? If this was your first book by the author duo, did it make you want to explore more of their work?

3. The friend group, a “chosen family” of academics, is a central element of the story. What was your initial impression of this group dynamic, and did your feelings about the friends change as the central deception unfolded?

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

1. Millie creates the “Catherine” persona as a way to express a more vulnerable, authentic version of herself that she feels she can’t share in person. Have you ever felt that it’s easier to be honest or open up under the safety of a screen, whether on social media, in text messages, or through other digital platforms?

2. Reid is deeply hurt by Millie’s deception, not just because she lied, but because she didn’t trust him with her true self. In your own relationships, what do you consider more damaging: an outright lie or the feeling that someone is deliberately hiding parts of themselves from you?

3. The friends are initially hesitant to risk their stable group dynamic for the uncertainty of romance. What do you think are the biggest risks and potential rewards of a friendship evolving into a romantic relationship?

4. Millie uses her sharp intellect and humor as a defense mechanism to keep people at an emotional distance. What are some ways you’ve seen people, or perhaps even yourself, use a particular strength or personality trait to avoid being vulnerable?

5. What do you think of Ed and Alex’s decision to help Millie with her final message as Catherine? Do you see their actions as a sign of loyalty to a friend in need, or do you feel that they became unethical accomplices in the deception against Reid?

Examine the book’s relevance to societal issues, historical events, or cultural themes.

1. The story is deeply rooted in the world of online dating, from crafting the perfect profile to being “ghosted.” In what ways does the novel accurately reflect the highs and lows of searching for connection in the digital age? Does it offer a hopeful or a cynical view of finding love online?

2. The idea of a “chosen family” is central to the novel, with the friend group providing the primary emotional support system for its members. How does this book reflect a broader cultural shift toward building community and family structures outside of traditional biological ties?

Dive into the book’s structure, characters, themes, and symbolism.

1. How does the novel’s structure, which alternates between Millie’s and Reid’s first-person perspectives and includes their group chats, create dramatic irony? How did knowing more than the characters did affect your experience of the story’s central conflict?

2. All members of the friend group are academics whose demanding careers have left them with little time for a social life outside their insular group. How does the novel use this university setting to explore the challenges of balancing professional ambition with the search for personal fulfillment and love?

3. What role does the “half-night stand” play in the story? How does it develop from a literal event to a metaphor for Millie and Reid’s struggle to connect emotionally, even when they are physically intimate?

4. Millie’s academic focus is on female serial killers, particularly poisoners. How does this unique character detail function as a symbol for her own behavior, as she uses a covert deception to navigate her complicated feelings for Reid?

5. The novel is a quintessential example of the “friends-to-lovers” trope, echoing stories like When Harry Met Sally…. How does the established history and deep platonic bond between Millie and Reid create higher emotional stakes compared to a romance where the characters begin as strangers?

6. Chris, Ed, and Alex each offer distinct perspectives on dating. Chris is cautious and protective, Ed is a bit hapless, and Alex is cynical and superficial. How do these secondary characters serve as foils that highlight different aspects of Millie’s and Reid’s own approaches to love and intimacy?

Encourage imaginative and creative connections to the book.

1. Imagine you are tasked with creating a “real” online dating profile for Millie after the events of the book. Based on her growth, what would her bio say now? What photo would you choose to represent the integrated, vulnerable person she has become?

2. If you could write one more group chat conversation to take place a year after the epilogue, what would the five friends be talking about? What inside jokes would they be making, and what would it reveal about where their lives and relationships are now?

3. Suppose you were a new professor who joined the UC Santa Barbara faculty and was befriended by the group right after Reid’s tenure party. What advice would you have given Millie or Reid as you watched their dynamic begin to change?