It follows three young women in Tuscaloosa, Alabama, from summer camp to college. Opening with a harrowing account of Sarina's mother attack on her in an attempt to fix her disfigured fingers, it follows her friendship with Nicole, who's mother is even more intent on her daughter's physical and social perfection, as well as the experiences of Bitty Jack, the daughter of the summer camp caretakers whose life continues to intersect with those of Sarina and Nicole.
Nicole's mother makes clear the connection between the South and rigid expectations of femininity in her succinct statement, "“…this is the South. We roll our hair and we wear lip gloss” (66).
Unlike Little Jack, those who choose to be ugly occupy a position of privilege; they choose ugliness as a form of rebellion, usually against insistent (or in this novel, draconian) mothers who are adamant about ensuring that their daughters will fit properly into the marriage economy. In order to choose ugliness, young women must first have access to the system in order to choose to opt out of it. For Nicole, making herself ugly is an attempt to connect to her friend Sarina. Nicole's obsession with Sarina is both a way of rebelling against her mother (who doesn't approve of the friendship) as well as an expression of lesbian desire, which is strictly forbidden in this community: “With Sarina, Nicole made an effort to play down her beauty. She didn’t powder her nose. A zit was like a door prize that she’d never try to hide. Who cared what her date thought? Not Nicole—one single bit. Her unfinished face put Sarina at ease. When Sarina was at ease, she was more attentive to Nicole. She accompanied her to the rest room, to get popcorn, refill their drinks. Anytime Nicole could steal Sarina from her date” (66).
In contrast to Sarina’s and Nicole’s mothers, whose insistence on their daughter’s beauty provokes rebellion, Bitty Jack’s mother sees beauty even in the freaks. Upon witnessing “Little Miss Hose and Pony,” she whispers, “She has such a pretty face” (89). Though she does not consciously make herself ugly, like Nicole, Bitty Jack's appearance is, to a certain extent, also mutable, especially once she learns how context-dependent value judgments about appearances are. When she gets a job in a freak show, hosing off Johnny Iguana, the “Freak Boss” says, “You’ll get along fine with him. I can tell. You wouldn’t be here unless you was an ugly duckling once yourself,” to which Bitty Jack replies, “I’m no swan” (81). At the freak show, however, the Freak Boss tells Bitty, “You’re not chicken shit…around here, you’ll be the belle of the ball….What you got? Glasses? Skin that’ll clear up sooner or later. Freckles. You’re skinny, but you’re nothing to turn your nose up at” (81).
The Freak Boss has a clear understanding of the benefits of ugliness. Regaling Bitty Jack with the story of the 300 pound woman who fell into the Pick a Duck pool, who “was flailing around like a pig in shit….Poor ducks were stuck in every crevice of her body,” he goes on to say that “Someone got the whole ugly incident on camera. Won ten grand on that goddamned embarrassing video show,” and he ultimately wonders whether she staged the whole thing (92-3).
At the fair, Bitty Jack's ugliness gets her access (and training) that allow her success—winning the big pig prize which eluded Stewart. When we first see Stewart and Sarina at the fair, we’re tempted to believe them that the games are fixed, although Sarina’s response to the Pick a Duck game—“The ugly bitch behind the counter kept giving Stewart small prizes” (54) seems excessive. When we later learn that the ugly bitch is, in fact, Bitty Jack, it illuminates the kind of unique power which ugliness grants Bitty Jack.
Bitty Jack’s account of the story includes her own self-appraisal: “Bitty knew she was no swan. Her beauty wasn’t storybookish: no dragon returns to find Bitty’s face morphed into a pot of gold. She still had to wear glasses. The shower was a war zone against combination skin. But she wasn’t the same girl she was at thirteen. Bitty knew she had bettered. She looked different, but not that different” (95). The power she holds over the Pick a Duck game is to give the small prize—the plush snake—in exchange for every duck that Stewart picks, and to refuse to give a purple snake, Sarina’s requested prize if they can’t win the big prize of the plush pig. As Stewart’s frustration mounts with each additional consolation prize snake, “Within minutes, Sarina stood like Medusa’s maid of honor. A wilted bouquet of bold-colored snakes drooper from her grasp” (96).
It is significant that she is Medusa’s maid of honor, and not Medusa herself. In this scenario, Bitty does not grant Sarina the full power of Medusa. Instead, Bitty Jack retains her power, and it is her silent stare which drives Sarina mad, making enough of a commotion that she is asked to leave the fair (96-97).
What this novel ultimately emphasizes is that ugliness in the South is synonymous with rebellion and dissent. After Nicole’s bloody cutting experience at the Tri Delt house, and her attack on her mother at the Tri Delt Poker Party, the incident is referred to as an “ugly situation” (178)--an extreme version of the warning given by so many southern mothers to their children to not "be ugly." What Eating the Cheshire Cat does is highlight how the imperative for southern women to fit into such narrow parameters of beauty results in a desire and drive to "be ugly"--both in appearance and in behavior.