When Happily Ever After Fails

Twentysomething Abigail Gardner's life is circling the drain. Her parents are dead, her “like a brother” is in love with her, and her nascent career as an art teacher was fully squashed by an unfortunate viral incident involving sophomores and Spanx. But just as that whirlpool feels poised to suck her down completely, she's granted a second chance: she lands a teaching job at Excelsior Primm, one of Philadelphia's oldest and most prestigious preparatory academies. Only problem is, instead of teaching art, she'll be stuck teaching her least favorite subject, literature, and her least favorite theme: tragedy.

Tired of being trapped in her own tragic tale, Abigail starts rewriting every sad ending she can get her hands on. To her surprise, her life soon starts to resemble the fairy tales she adores — great job, hot guy, a career gaining recognition. But when an unexpected plot twist threatens to derail her happy ending, Abigail begins to realize why these conclusions are so hard to come by.

This discussion guide was created and shared by the author, Courtney Deane.

Book club questions for When Happily Ever After Fails by Courtney Deane

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

How do you think you would have responded if you had met a girl like Abigail – young twentysomething, no parents/siblings, trying to find her footing in life – at the beginning of her journey?

What did you think of such an unorthodox meet cute?

If you were to adopt a fake identity a la Abigail at the bachelorette party, what would your story be? What would the outfit look like?

What did you think of the “love triangle”? Do you feel the right man won out in the end?

How do you view Mitch’s role in relation to Abigail?

If you could give one piece of advice to Abigail – at any point along her journey – what would it be?

What was your opinion of Quinn? Did it change at all throughout the book?

In your opinion, what does Abigail’s ideal “happily ever after” look like to her? To you?

What were your biggest takeaways from this book?

Who do you envision actor-wise when you think about this book as a TV show or movie?

When Happily Ever After Fails Book Club Questions PDF

Click here for a printable PDF of the When Happily Ever After Fails discussion questions

“The end result is an expansive tale that will have the reader rooting for happily-ever-afters…A strong debut romance for fans of true happy endings.” —Kirkus Reviews

“Courtney Deane offers up a radiant debut in When Happily Ever After Fails. Whip-smart and relatable, Abigail's search for her own happy ending will have you on the edge of your pool chair. An absolute must read this spring!” —Liz Fenton and Lisa Steinke, authors of Forever Hold Your Peace

“A brilliantly funny faking-it rom-com. . . . witty, well-paced, and original. Gimme all the Courtney Deane books with a big glass of rosé, please!” —Lizzy Dent, author of The Summer Job and The Sweetest Revenge

“This is a stirring romance that the great William Shakespeare would appreciate.” —Readers’ Favorite (five-star review)

“Courtney Deane is a fresh, fabulous new voice in the women's fiction world. Her debut novel is an absolute gem - heartfelt, hilarious, and deeply moving. I'll be watching and cheering as Ms. Deane's career takes off at what I'm certain will be a furious pace." —Melanie Summers, author of The Honeymooner

“Courtney Deane’s debut is a novel in which you do not only root for the characters, but you believe in them. This book is for anyone who has ever tried to find their way and especially for those who still are.” —Gigi Garrett, author of Her Fake Engagement and Miss Christmas (now adapted as a Hallmark Christmas movie)

“…a charmingly astute romantic novel…”

—Seth Combs, San Diego Union Tribune

"Courtney Deane’s novel is an entertaining read that will keep you turning pages. The reader is taken on a ride with Abigail as she grows into herself and finds her voice. Deane makes it easy to root for Abigail along with the other quirky characters who have distinct and interesting personalities. When Happily Ever After Fails is a fun debut."

—Leslie A. Rasmussen, author of After Happily Ever After and The Stories We Cannot Tell