1. In THE UNFORTUNATE IMPORTANCE OF BEAUTY, both Barb and Lily don disguises, of opposite kinds, to hide what they really look like and thereby attract the man of their dreams. Can we consider Barb and Lily as foils for one another in the novel? Are their troubles finally the same or different?

2. Barb, Georgia and Lily are all artists. What kind of distinction does the novel make between physical beauty and artistic beauty? Which is more powerful? More important? Can one get in the way of the other? Can one serve the other? How?

3. Would you consider THE UNFORTUNATE IMPORTANCE OF BEAUTY to be a comedy of manners? A murder mystery? A modern fairy tale? Or all of the above? Why?

4. The novel presents us with two different forms of love: love between friends and romantic love. Which is more powerful? More important? What is the relationship between love and beauty in the novel?

5. Which scene in the novel did you find funniest? Why?

6. Would you argue that the love between Strad and Lily is real, even though it is based on a lie? Why or why not?

7. Do you trust that Peter would have fallen in love with Barb even if he had not known what she really looked like? Why or why not? Does it matter?

8. Penelope earns her living by convincing customers that they have broken her ugly clay pots. Of this line of work, Barb says she “wouldn’t be surprised if the art of deception became the true art of the piece.” Do you agree with Barb that Penelope is a kind of artist in her own right? Why or why not? How does her form of beauty, and art-making, play into the themes established by Barb’s and Lily’s?

9. How does the background information that we get about Barb’s parents help us understand her relationship to her own beauty? Is it really Gabriel’s suicide that causes her to don her disguise, do you think, or had her mother’s story been troubling her as well?

10. How “happy” did you find the ending? How did it resolve Lily’s and Barb’s more existential problems with the nature of physical beauty and of romantic love?

11. How important has physical beauty been in the trajectory of your own life? Do you ever wish you could try on another face? What difference do you think it would make?