Gather initial thoughts and broad opinions about the book.

1. The novel is described as a homage to 1990s romantic comedies, especially the films of Nora Ephron like When Harry Met Sally… or You’ve Got Mail. For those who’ve seen these movies, how did reading this book feel in comparison? What classic rom-com elements did you enjoy seeing, and what aspects felt updated for a modern audience?

2. Did you find the “opposites-attract” dynamic between the meticulously organized Jackson and the more spontaneous Delilah compelling from the start? What was the moment in the story where their chemistry really clicked for you, and why?

3. The story blends lighthearted romance with heavier themes like workplace sexism, emotional neglect, and caring for a family member with Alzheimer’s. How successfully do you think the author balanced these different emotional tones?

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

1. Jackson relies on rigid schedules and routines to manage his anxiety and feel in control of his chaotic life. How do you handle feelings of stress or unpredictability in your own life? 

2. Borison describes Delilah’s “sunshine girl” persona as a deliberate professional strategy and a personal defense mechanism. Have you ever felt pressure to present a certain version of yourself at work or in social settings? 

3. Delilah and Jackson’s non-traditional family units are central to the story. Are there ways in which your own family or the family of someone close to you looks different from a traditional nuclear family? 

4. Delilah must navigate a toxic work environment created by her boss, Keith. Have you ever experienced this kind of overt discrimination in the workplace? How did you handle it? 

5. Jackson’s decision to go sledding in a blizzard and Delilah’s choice to quit her job on live TV are huge leaps of faith. Can you recall a time when you stepped outside your comfort zone? Did that experience change your perspective?

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

1. In what ways does the novel critique a workplace culture that devalues personality traits often associated with femininity, like warmth, empathy, and whimsy? Where do you see similar dynamics playing out in the real world today?

2. The story is firmly rooted in its Baltimore setting, featuring real local landmarks. What role does a strong, specific sense of place play in a contemporary romance novel? How did the details of Baltimore and western Maryland affect your reading experience?

3. The “hot-mic” incident turns Jackson and Delilah into a viral sensation, complete with a hashtag and remixed fan edits. What does the novel convey about modern fame and the way social media can transform private moments into public entertainment?

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

1. Post-it notes track the evolution of Jackson and Delilah’s relationship. How does this recurring motif function as a physical representation of their enemies-to-lovers journey?

2. How does the alternating first-person narration from Jackson’s and Delilah’s perspectives shape your understanding of their internal struggles? How would the reading experience be different if the story had been told from just one character’s perspective?

3. Jackson and Delilah’s supportive friends, like Aiden and Gianna, play an important role in the novel. How do these secondary characters help drive the protagonists’ personal and romantic development?

4. Many contemporary romances feature the enemies-to-lovers and forced-proximity tropes. How does this book’s use of these conventions compare to other stories you’ve read in the genre, such as Sally Thorne’s The Hating Game? What felt fresh or unique about Borison’s approach?

Encourage imaginative and creative connections to the book.

1. If you were producing a TV segment for Delilah after she gets her job back, what kind of story would you assign her? Design a segment that showcases both her scientific expertise and her unique, joyful on-air personality.

2. Imagine you could add one more Post-it-note exchange between Jackson and Delilah at any point in the story. What would the notes say, and at what moment would you place them to reveal something new about their feelings for each other?

3. The book’s Epilogue hints that Jackson is carrying a ring and waiting for the perfect moment to propose. Write an additional scene that depicts that proposal. What setting would you choose, and what small details would make it uniquely “Jackson and Delilah”?