When I Was Puerto Rican is a real-life coming-of-age story that should be of special interest to American students. Puerto Rico, the "fifty-first state," has an anomalous status as both American and Hispanic, or "foreign." Esmeralda Santiago gives an extraordinary insight into what it is like to be Puerto Rican, both on the island and as an immigrant in New York City.

Esmeralda (nicknamed "Negi") narrates the story in a simple style, relating the often heartbreaking events of her childhood gently and without judgment. Negi spends her early childhood in the poor but beautiful Puerto Rican countryside. It is the Eisenhower era and the Americans are trying hard to "Americanize" the island, but the children's life is an idyllic one, and they enjoy a freedom unknown to urban children. The beauty of this life, however, is marred by the conflicts in their parents' union: Mami and Papi have seven children together but fight bitterly and remain unmarried, and Papi continues to see other women.

After a tortuous series of separations and reconciliations, Mami decides to break away from Papi, and she takes her brood to Brooklyn, "a place said to be as full of promise as Ponce de León's El Dorado." [p. 37] While devastated at leaving her beloved home, Negi bravely accepts her new life, in the process becoming what she would later call a "hybrid": both Puerto Rican and American. Determined to escape the ugliness of her family's life in Brooklyn, she works hard to be accepted to the High School for the Performing Arts in Manhattan, from which she goes on as a scholarship student to Harvard.

Esmeralda Santiago's story gives insight into the lives of many thousands of immigrants to America. While remaining very much a part of the world they left behind, the immigrants are faced with a new language, a new culture, and new expectations and codes of conduct.

Selected Questions from the Teacher's Guide

1. What is a jíbaro? What positive connotations does the word have? What negative ones? What does the word mean to Negi? Why is Negi called a jíbaro in Santurce but not in Macún?
2. How does the Santiago family celebrate Christmas? Is it a religious holiday for them or simply a family festival?
3. What is the function of the community center in Macún? Why do the Americanos want the children of Macún to substitute American foods for their own foods? Why is the program eventually abandoned?
4. Who are Dick, Jane, and Sally? Are they appropriate models for the children of Macún?
5. What is a jamona? What is the difference between a jamona and a senorita? Is there a male equivalent of a jamona? Why is the word a pejorative one in the Puerto Rican culture? Are there such negative connotations in American culture? How does Negi herself feel about the possibility of remaining jamona?
6. Why does Mami decide to get a job for the first time? Why does she dress so differently in order to go to work? What kind of a taboo is Mami breaking in going to work? Why does she evoke such hostility in her neighbors? Why do the women, in particular, resent her? How does Papi feel about Mami's job? And Negi?
7. The Santiago children play Caribs and Spaniards. What American game would this resemble? What activities are likely to occur in it?
8. How do the Puerto Ricans' interactions with Italians, Jews, and morenos (African-Americans) differ? How do these groups treat Puerto Ricans?
9. How does the feast Tata provides for her grandchildren differ from the feasts the family enjoyed in Puerto Rico?
10. What does Marilyn Monroe symbolize for the young Negi?
11. Explain the meaning of the word sinvergienza. How does Mami apply it to Papi? How does this concept add to stress between the sexes in Macún?
12. How would you define the word dignidad? Is it a code of manners, or of morals? Do the members of the Santiago family show dignidad to the outside world? Do they show it to each other? Does contemporary American mainstream culture have an equivalent of dignidad? If so, how does it manifest itself?
13. In Macún women are expected to behave differently from men. In what ways are men allowed to express their feelings and opinions more directly than women? What special constraints are put upon women in the culture?
14. What is the significance of the book's title? Does the author feel that now, as an American, she is no longer a Puerto Rican? In what way is Negi irrevocably changed by her move to the United States? What does she mean when, at the end of the book, she calls herself a hybrid?
15. In writing When I Was Puerto Rican, Esmeralda Santiago encountered difficulties in finding appropriate English terms for some of the Puerto Rican concepts she was trying to convey. She decided to leave many of these words in Spanish, providing a glossary at the end of the book. Can you explain why she might have had such difficulty finding English terms for concepts like dignidad, jíbaro, or toda una senorita?