Fair Rosaline

Was the greatest ever love story a lie?

The first time Romeo Montague sees young Rosaline Capulet he falls instantly in love. Rosaline, headstrong and independent, is unsure of Romeo's attentions but with her father determined that she join a convent, this handsome and charming stranger offers her the chance of a different life.

Soon though, Rosaline begins to doubt all that Romeo has told her. She breaks off the match, only for Romeo's gaze to turn towards her cousin, thirteen-year-old Juliet. Gradually Rosaline realizes that it is not only Juliet's reputation at stake, but her life. With only hours remaining before she will be banished behind the nunnery walls, will Rosaline save Juliet from her Romeo? Or can this story only ever end one way?

Shattering everything we thought we knew about Romeo and Juliet, Fair Rosaline is the spellbinding prequel to Shakespeare's best known tale, which exposes Romeo as a predator with a long history of pursuing much younger girls. Bold, lyrical, and chillingly relevant, Fair Rosaline reveals the dark subtext of the timeless story of star-crossed lovers: it's a feminist revision that will enthrall readers of bestselling literary retellings such as Hamnet by Maggie O'Farrell and Hester by Laurie Lico Albanese.

This discussion guide was shared and sponsored in partnership with Sourcebooks Landmark.

Book club questions for Fair Rosaline by Natasha Solomons

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

What are Rosaline’s objections to entering the convent? Would any of her other options allow her to have all the things that she wants?

What initially attracts Rosaline to Romeo? How does he initially compare to her idea of “A Montague”?

Describe Rosaline and Tybalt’s relationship. How does their time apart change their childhood closeness?

How does the feud between the Montagues and Capulets color Rosaline and Romeo’s early interactions? How does she feel about keeping their identities secret while out together and the truth of their relationship to herself?

What does Romeo want from the girls he seduces? How does Rosaline disappoint those expectations?

How does Tybalt react when Rosaline finally tells him the truth of her situation? What did she hope to gain by telling him?

Rosaline struggles to get Juliet to see the danger that she is in and knows that she was just as stubborn in Juliet’s position. Can you think of a character whom Rosaline might have respected as she eventually breaks through to Juliet?

What role does pride play in the book? In what scene does a character’s pride cause the most harm?

How do Paris and Romeo compare in their pursuit of Juliet? Are their goals the same or different? Do you agree with Rosaline that Juliet’s parents are to blame for the way the two men made a victim of Juliet?

At the beginning of the book, Rosaline’s freedom is the virtue she holds most dear. By the end she sacrifices it to earn the abbess’s help. What changed for her?

Fair Rosaline Book Club Questions PDF

Click here for a printable PDF of the Fair Rosaline discussion questions

"Irresistible. An excellent spin on a timeless classic." ―Jennifer Saint, Sunday Times bestselling author of Ariadne

"I have not been able to stop thinking about this book . . . Fair Rosaline is a gripping, spellbinding and wonderfully immersive book - and one that truly makes you think. I would be very surprised if everyone is not talking about it.." ―Elodie Harper, Sunday Times bestselling author of The Wolf Den

"A brilliant, feminist re-imagining of Romeo and Juliet, Fair Rosaline is a gorgeously written version of Verona from Juliet's cousin, Rosaline's, point of view. What does Romeo truly look like through the eyes of a woman on the periphery of the original story? Natasha Solomons skillfully shows us another version of the star-crossed lovers - and the Romeo --we all think we know. I absolutely devoured this thought-provoking, female-centric take on Shakespeare." ― Jillian Cantor, USA Today bestselling author of Beautiful Little Fools