The Big Day

For fans of Sloane Crosley, another mostly true memoir from the acclaimed author of Sit, Cinderella, Sit about whether she’s finally ready for marriage before she turns fifty.

For years, Lisa Cheek believed commitment wasn’t in her genes. Her dating patterns were clear—date a lot and widely, but never settle down. When anyone wanted to marry her, she backed away. So even she is surprised when, at forty-nine, she finally says “yes” to a proposal and commits fully to her boyfriend, Big Johnson. But when she finds out on their wedding day, after the vows, that they aren’t actually married, she hesitates. Should she take this as a sign to run while she still can?

In The Big Day, Lisa Cheek invites us to witness her wedding day, with all its hilarity, chaos, and unexpected turns. Throughout, she reviews both her past relationships and the marriages of her family and friends, analyzing the choices of others and reliving the biggest ups and downs of her own love life. Ultimately, she must decide once and for all whether she’s just not marriage material—or if she’s finally found a love worth staying for.

These discussion questions were provided by the future of agency.

Book club questions for The Big Day by Lisa Cheek

Use these discussion questions to guide your next book club meeting.

The book opens with a wedding-day revelation that the marriage may not be legally valid. How did this moment shape your expectations for the story? Did it change how you interpreted everything that followed?

Lisa reflects on memory as subjective and imperfect. How does this framing influence your trust in her storytelling? Does it make the narrative feel more or less authentic?

Throughout the book, Lisa examines her own role as the “common denominator” in her relationships. How did this affect your understanding of her past relationships?

Family plays a central—and often chaotic—role in Lisa’s life. How did her upbringing (divorce, stepfamilies, instability) shape her views on marriage and commitment?

Lisa receives multiple marriage proposals before ultimately saying yes. Why do you think she said no in the past—and what made the proposal from Big Johnson different?

Humor is a defining feature of the book, even in painful or confusing moments. How does humor function as a coping mechanism for Lisa? Did it deepen or distance your emotional connection to the story?

The concept of “The Big Day” is often culturally idealized. How does this book challenge traditional narratives about weddings and marriage?

How do societal expectations—particularly around age and marriage— impact Lisa’s decisions and self-perception?

The book includes many different romantic partners (e.g., “The Musician,” “The Actor,” “The Ghoster”). What patterns do you notice across these relationships?

What do you make of Lisa’s repeated observation that many couples never take a honeymoon? Do you see this as a practical reality, a symbolic omission, or something else entirely—and why?

How does Lisa’s relationship with independence evolve? Does marriage feel like a loss of independence, a gain, or something more complex?

What role does friendship play in Lisa’s understanding of love and partnership, particularly as reflected in the wedding vows?

By the end of the book, do you think Lisa has a clearer understanding of what she wants from love and relationships? Why or why not?

The Big Day Book Club Questions PDF

Click here for a printable PDF of the The Big Day discussion questions