Cupcake Brown’s shocking memoir is a devastating and inspiring story. Through intimate details and family memories, she chronicles her life from age eleven through her midtwenties: a challenging time for the average person, and in her case, an extraordinary journey through alcoholism, drug addiction, prostitution, gangbanging, and numerous unhappy households.
Through all the hellish circumstances and heartbreak, Cupcake’s hopeful spirit and lucky breaks pulled her through the trials of her life. This rousing story tells all–the good, the bad, and the very ugly. And ultimately we get to know a woman who has faced the challenges life handed her with humor and grace.
Questions and Topics for Discussion
1. How do you think Cupcake and Larry’s trail through the foster care system would have been different if they’d been close? Do you think it would have helped either of them later in life?
2. On page 10 Cupcake says, “That was one thing about me. I didn’t have many people in my life, but those I had I loved fiercely.” Do you think this changed as she moved through the foster care system, and then on to drugs, drinking, et cetera? Why or why not?
3. Discuss the adult figures Cupcake had in her life while she was growing up–Daddy, Jr., Mr. Burns, Diane Dobson. With these role models, could she have found a better way out of her situation than turning to drugs and alcohol?
4. Why do you think Cupcake was so easily swayed by the thinking that “nothing comes for free”? How did she make the leap from applying this thought to material items and food to less concrete realities like love and acceptance?
5. Do you think Cupcake would have changed her ways earlier if she had been able to complete her first pregnancy? Or like Kelly, would the partying, drinking, and drugs have won out over a child? Do you think having someone to look after the baby for her would have influenced her either way?
6. Why do you think Cupcake had several abortions after her first lost pregnancy? Was it simply a matter of wanting to live a fast life, or do you think she was afraid to let herself love and be responsible for another person?
7. Cupcake finally admits to not liking herself, and begins the long road to developing self-acceptance, self-worth, and self-love. Have you ever struggled with your self-image or self-worth? If so, did Cupcake’s story help you in any way?
8. On page 308, the cop “Preacher” says to Cupcake, “Now don’t get me wrong. Nobody belongs out here. But some people . . . well, they need to be here. They don’t want anything better for themselves. They’re too far gone. They don’t want to come back.” What do you think “Preacher” saw about Cupcake that convinced him she wasn’t one of the people who “don’t want to come back”? Do you think Cupcake began to listen to him at this point?
9. On page 326, Cupcake says, “I’d quit talking to Daddy and Jr. because all we did was argue: they fussed about how I was fucking up my life, and I wanted to know if they had any money I could borrow. In my mind, unless they had money to give, we had nothing to talk about.” Discuss the similarities between Cupcake’s attitude here and Mr. Burns’s attitude toward the life insurance money. Do you think Cupcake realized the similarities? Do you think she would have changed her ways if she did?
10. Compare and contrast the roles that Fly and Larry played in Cupcake’s life. Why do you think she allowed Fly to be more of a brother to her than Larry? Did it have to do with their gang participation?
11. On page 411, Venita asks Cupcake if she ever grieved for her mother. Do you think Cupcake could have avoided her addictions and problems if someone had taken the time to ask this and help her through the stages of grief?
12. Discuss the inspirational qualities of a story like Cupcake’s. Has her story influenced you to make any changes in your own life?