On Monday morning, Tom dreads going to school. He considers what might convince Aunt Polly to let him stay home. He decides to go with his sore toe.
Though Monday always begins a new school week, Tom always tried a way to avoid this routine.
Tom's moaning awakens Sid, who rushes find Aunt Polly. Tom complains: "O, auntie, my sore toe's mortified!" Aunt Polly sees through his act, and can't help but laugh.
Tom exaggerates his pain, and uses the wrong word to do so, making Aunt Polly to laugh. The interaction embodies their affection for one another, and though she should scold him, his ridiculousness entertains her.
Tom tells her that his toe really had been hurting—even more than his tooth. She declares that the tooth should be removed. Tom is terrified, protesting that the tooth doesn't hurt after all, and that he'll go to school. Aunt Polly proceeds to tie one end of a string to his bed-post and the other to his tooth. When she lunges at him with a flaming coal, he jumps away, and the string yanks out his tooth.
If Tom had simply admitted that he was faking, rather than using his tooth as an excuse, he might have avoided the extreme pain of having it pulled. Aunt Polly's efficiency at removing the tooth show how formidable and capable a woman she is, and Tom is lucky to have her looking after him. He's also lucky she doesn't punish him with as severe floggings as she might.
On the way to school Tom shows his schoolmates his newfound spitting abilities thanks to the gap from his missing tooth.
Tom manages to turn most any set-back into an opportunity to gain glory. Though adults consider it a grotesque act, spitting is acclaimed by boys.
Tom runs into Huckleberry Finn, who shows him a dead cat he says can be used to cure warts. Tom argues that spunk-water, the puddle that forms on a tree stump, is better. They agree to meet up at midnight to test the cat method.
As another orphaned boy, Huck is Tom's counterpart in St. Petersburg. Huck does not have Aunt Polly or any other caretaker, however, leaving him free to play hooky, sleep outdoors, smoke, avoid bathing, and generally live as he pleases. This makes him, in a different way than Tom, the envy of every other boy in the village. While Huck's extreme rebellion often draws out Tom's competitive streak, as with their vying for expertise in curing warts, their deep friendship is founded in their love for make-believe, including all things superstitious.
Tom arrives late to school and his teacher, Mr. Dobbins, reprimands him. When Tom notices that his crush is now a classmate, he proudly declares: "I STOPPED TO TALK WITH HUCKLEBERRY FINN!" The teacher and students are shocked. Tom is spanked him and forced to sit with the girls.
Because he avoids socialization, Huck is highly esteemed amongst boys. They are forbidden to play with him, for he is a pariah associated with his drunkard father in the eyes of the adults in the village. Tom isn't mature enough to stand up for Huck against this unfair discrimination. Rather, he drops Huck's name to show off, knowing that the surest way to get the most attention imaginable is to behave as badly as possible.
Tom uses his seat to make contact with Becky. Though at first she frowns at him, she eventually accepts both a peach and a drawing, and tells him her name. He writes "I love you" on his slate, but their flirtation his interrupted by Mr. Dobbins. Tom goes to his original seat, elated.
If Tom can't physically escape the boredom of the classroom, he can at least indulge in romantic fantasies to ignore the master's presence. His ideas of love are overblown and unrealistic, for he hardly knows Becky.