In the early afternoon, Tom approaches Aunt Polly, who is dozing over her knitting. She is surprised to see him, because she secretly suspected that he would sneak away and leave his chore unfinished. When he says he is done, she does not believe it. However, when she sees that the fence is covered with several coats of whitewash, she is thrilled. Not only does she tell Tom that he can go out to play; she also rewards him with an apple. When she gives it to him, she delivers “an improving lecture” about how treats taste better when they are earned “through virtuous effort.” During this speech, Tom steals a doughnut.

Free from work for the rest of the day, Tom pelts Sid with dirt clods to get revenge for the yesterday's tattling incident. Then Tom runs to the public square, where boys are lined up to fight a battle. He is general of one of the armies, and his friend Joe Harper is the general of the other. They stand to one side giving orders while the two armies fight. When all is finished, the two sides count their dead, agree upon “the terms of the next disagreement,” and set the date for the next battle.

On his way home, Tom sees a new girl in his friend Jeff Thatcher’s garden. She is beautiful, with bright blue eyes, and Tom promptly falls in love. He stares at her until she notices him, and then he shows off with feats of gymnastics. She pretends not to watch, but when she goes inside she throws a pansy to him. He does not want to be seen with it, so he picks it up with his toes and runs around the corner to pin it beneath his shirt. Then he returns to her gate and shows off until dark, hoping she might see him through a window.

At dinner that night, Sid breaks the sugar bowl while Aunt Polly is out of the room. Tom is gleefully imagining Sid's punishment when Aunt Polly comes in, assumes that Tom is guilty of the crime, and smacks him instead. When he informs Aunt Polly of her mistake, she wants to apologize, but she does not feel it would be good discipline. She says that Tom probably deserved the smack “for some other owdacious mischief.”

After this incident, Tom spends the whole evening feeling sorry for himself. Aunt Polly is so sorry that she is on the point of tears, but Tom does not forgive her. He slips out of the house, sniveling over the tragedy of his life. He imagines how it would be if he got sick and died. He is sure that Aunt Polly would wail over his corpse and wish she had never punished him for anything, ever. He walks to the new girl’s home and climbs into her yard, thinking how romantic it would be if he died beneath her window.

Tom’s imaginings are interrupted when one of the new girl’s servants throws open a window and tosses a bucket of water on Tom. He leaps up and runs home. Sid, who is already in bed, peeks out from beneath the covers and sees Tom inspecting his wet clothes. He wants to tease, but he notices “danger in Tom’s eye” and decides not to risk it.