The mother-daughter relationship drives the plot in Annie John and is its primary theme. The difficulties and tensions in this relationship stem from Annie's inability to accept the fact that she is a separate self. Kincaid paints Annie's desire to remain united with her mother as an emotion shared by most girls of her age. Annie's classmates all commiserate with her essay about her fear of separation. Furthermore, the girls befriend one another in an effort to find substitutes for the maternal love that appears to be dissipating. As Annie ages, she finds herself caught between love and hatred for her mother, which drives her to be both a good student and a disobedient child. Again, the rationale behind her adolescent rebellion seems to be proffered as an explanation for a general psychological trend rather than merely a specific fictional phenomenon. The dynamics of mother-daughter relationships take up a prominent place in Jamaica Kincaid's work and have frequently appeared in her other novels such as Lucy and The Autobiography of My Mother.
Antigua was colonized by the British until 1967 and remained a commonwealth in 1981. As Annie John takes place in the 1950s, it remains in the colonial period. Kincaid explores the colonial relationship particularly through her discussion of the school that Annie attends. It is run as a British institution and all the materials taught in the school deal with English literature, history, and culture. The girls dress in a formal British style and they are discouraged from engaging in local activities, such as calypso dancing in the playground. Annie's musing on the failure of the school to discuss the negative history of slavery and her delight in the imprisonment of Columbus highlight the ways in which the school teaches the students not to question the history and social order that is being handed down to them. Annie excels in her school, which shows that she has learned all of the skills necessary to prove her intellectual and social worth in the colonial world. However, her spunky behavior behind the teachers' backs shows that her feisty Antiguan spirit still thrives within.
Although Annie's father appears a gentle and reticent man, he serves as a testament to the unequal gender relations in Antigua. Annie's father is about thirty years older than his wife. He had numerous sexual affairs before marrying Annie's mother and the women with whom he slept frequently harass Annie's mother on the street. Now that he has his married life secured, he provides for the family while his wife takes care of his domestic and sexual needs. While as a man Annie's father could philander, Annie's mother interprets Annie's mere discussion with a group of boys as inappropriate sexual misconduct and calls her a "slut." With these two standards, it becomes clear that the behavior expected of men and women in Antigua are quite different. Although the women who curse at Annie's mother appear unfriendly, even Kincaid's depiction of them is sympathetic. They, after all, committed the same sexual act as Annie's father, but have been left in the difficult economic position of raising their children without a husband.
Obeah is the local spiritual system that relies upon the use of herbs as well as sorcery and spells. Obeah reappears many times in the novel from the way that Mrs. John takes a bath, to the healing of Annie, to the Obeah blessed clothing that Annie wears on her way to England. Obeah is a powerful part of the native culture that remains, despite the cultural dominion of the British Empire. In particular, Obeah links the Caribbean culture its pre-colonization people, while simultaneously suggesting the blend of Amerindian, African, and European cultures that make up the islands. Obeah particularly is intimately connected with strong female characters. The male figures in the novel, Annie's father and grandfather, both shun it. Annie's grandmother particularly seems to dwell in a mystical world of obeah that fully defies the logical world of the colonial culture. She arrives and leaves Antigua on days that the ferry does not run, for example. She is the only one to be able to heal Annie, despite the efforts of the obeah woman and the local Doctor. The existence of obeah in Annie's world demonstrates the power of the local spiritual beliefs to survive, despite the colonial conditions.
Water reappears through the novel as a powerful natural force that helps to both heal and transform. Its ability to heal can be seen in the baths that Annie and her mother take at the beginning of the novel. The salt water of the ocean likewise strengthens Annie's kidneys. The rainstorm that persists during Annie's illness cleanses and transforms the island while providing a nourishing environment for her to recover. Finally, the ocean allows for Annie's ultimate rebirth by pushing her on her way toward a new life in England. Kincaid's use of a powerful natural element as a fictional tool carries an edge of magical realism that is consistent with a Caribbean setting in which magical practices such as obeah play such an important role.
Annie obsesses over death in her opening chapter and initially, the idea of death portends the possibility of separation that Annie fears. As the novel continues, the idea of death reappears amongst the tombstones upon which Annie and her classmates usually sit during recess. These tombstones belong to old white people, meaning former colonial slave owners, who once governed Antigua. The young Antiguan girls now sit on the tombstones and sing dirty songs or show each other their body parts while making inappropriate comments. Here the image of death is placed next to the idea of life and seriousness of these old men's death seems joked upon by the fact that barely teenage girls are primping on their graves. The constant return of the girls and the narrative to the tombstone area testifies to Kincaid's ironic commentary upon the history that these colonial masters represent.
Annie's mother trunk and the other trunks in the story symbolize the self. When Annie is a young girl, her favorite pastime involves looking through her mother's trunk. Annie uses the stories about the objects in the trunk to define who she is. At that young age, Annie shares her mother's trunk because she has no separate self of her own. Annie's mother trunk came all the way with her from Dominica and therefore seems to be the object that contains all the family history. Eventually when Annie decides that she has a separate self, she wants her own trunk. It, in turn, will become her history and a representation of her self, as her mother's was for her. When Annie leaves Antigua for England, she brings her trunk with her. Her trunk bears a label that reads, "My name is Annie John," a strong affirmation of Annie's new sense of self.
The first two marbles that Annie receives are given to her by her mother after they arrived free in a package of oats. One is white with blue and the other is white with yellowish brown. Annie thinks that the one with blue represents the oceans, while the one with brown represents the landmasses of the world. In fact, these marbles and the ones that Annie subsequently gathers represent the new world that she is creating for herself. After receiving her first marbles, Annie goes on to become a marble devotee. She wins marbles from everyone and gathers a small stash. Just as her marble career is getting underway, so too is Annie's world changing as Annie spends hours with the Red Girl, a representative of the non-socialized order. The time playing marbles will help Annie to see beyond the world that her mother and teachers outline. When Annie's mother furiously searches for Annie's marbles, what she really wants to find is not so much the little balls, but rather the new world that these marbles have opened up for her daughter. This world is one that defies the common social program and her mother does not want her to have it.
Annie's principal makes Annie copy Paradise Lost as punishment for having blasphemed Christopher Columbus in her history book. The specific use of Paradise Lost for this punishment is apt. The book describes how the angel Lucifer challenged God and was subsequently tossed out of the paradise of heaven into darkness and exile. Annie's current predicament is similar to that of Lucifer's. Annie wants to challenge the dominant power of both her mother, and by association the colonial order, but fears the fate of exile. The principal's choice of the book also carries an implicit threat, indicating how Annie will be punished if she continues to question the colonial authority that establishes Columbus as a hero. On the other hand, the idea of exile simply compounds Annie's already existent fears about being left all alone. The concept of a "lost paradise" also seems appropriate in Antigua, an island that may look like paradise but became a virtual hell when the British arrived and set up the institution of slavery.