1. As a single man, Edwin John Wintle had the freedom to come and go as he pleased, whether it was spontaneously catching a movie or jetting off to Europe. What is Ed’s motivation for taking in Tiffany and upending his lifestyle? Is it simply to help his sister out, or are there other reasons? What does he ultimately conclude about why he did it?

2. How did Megan’s own emotional issues factor into her relationship with Tiffany?

3. Were you surprised that Megan would give up her own child, even to a family member? Did she make the right decision by allowing Ed to become Tiffany’s guardian? Why or why not?

4. “For as far back as I can remember,” writes Ed, “Megan and I have had a volatile relationship” (21). What is the source of their contentious relationship? How does caring for Tiffany give Ed a better understanding of Megan as a parent? Ultimately, does Ed’s caring for Tiffany also improve his relationship with Megan?

5. Throughout Tiffany’s life, Ed had been a favored uncle and more of a friend to her. How does this dynamic change once he becomes the primary authority figure in her life? Is it possible for both aspects of their relationship to co-exist, or, as Ed asks himself, are they mutually exclusive?

6. What is your overall opinion of Ed’s parenting style? What missteps, if any, do you think he makes along the way? What would you have done differently if you were in his shoes?

7. Why does Ed’s father predict that the arrangement of his son taking Tiffany in will not work out? What does this attitude say about their relationship?

8. What are some of the challenges and benefits of raising a child in an urban environment such as New York City? In what ways does the geographic relocation help in Tiffany’s transformation?

9. How is Tiffany’s illness—including the period of time leading up to her diagnosis of mononucleosis --- a turning point both for her and for Ed? How does going through this ordeal change their relationship?

10. Tiffany sometimes exhibits selfish and unattractive behavior, such as throwing tantrums, blaming others for her mistakes, and spending her uncle’s money on things she is not supposed to. How much of her actions can be attributed to normal teenage behavior and how much to her tumultuous childhood? When does she begin to see that she has to take responsibility for her own actions? How much empathy did you feel for Tiffany?

11. Re-read the letter Tiffany writes to Ed after he forbids her to visit a friend who lives in the Washington Heights section of the city (pages 280-281). Is she justified in the things she says to Ed? What is his reaction to the “pure venom” in Tiffany’s letter?

12. How important are the roles that Eugene, Orly, and Ed’s other friends play in his life? Why are they so quick to accept Tiffany as a part of Ed’s life? How do they contribute to fostering a positive environment for her?

13. In what ways does parenting Tiffany compel Ed to look back on the choices he has made, particularly his career decisions? In what other ways does he learn more about himself during the first year with Tiffany?

14. The author shares some very personal details about himself in this book—failed romantic relationships, family dramas, mental illness, and his HIV-positive status. Were you surprised at his level of honesty? Why or why not? In what ways is Breakfast with Tiffany as much Ed’s story as it is his niece’s?

15. What does Breakfast with Tiffany say about the notion of family? What advice can parents and others who work with children learn from this book?

16. What did you enjoy most about Breakfast with Tiffany? What did you like the least?