Tristram elaborates again upon the necessity of moving backward and forward in time to tell his story. While he still intends to press on toward the story of Toby's love affair, he prepares us for the possibility that he may yet make some digressions along the way. He returns to his earlier suggestion that Toby was the last to know that he was in love, observing that if Susannah had not informed him of the matter, he might never have pursued the affair at all. Tristram launches into the story once, gets bogged down in rambling speculations, and decides to abandon the chapter and begin again.
When Uncle Toby and Corporal Trim first come down to the country to begin work on the fortifications, they find that the house is unfurnished. They are obliged to stay with Widow Wadman for three days, and by the third day she has fallen in love with Toby. Toby is so occupied with his battlements that it takes until the end of the war--eleven years, in fact--before he has leisure to attend to the situation with his smitten neighbor.
Tristram describes the Widow's advances toward Toby as a military maneuver. Separated from the site of Toby's battle replica only by a hedgerow, Mrs. Wadman is in a most strategic position to launch her attack. By feigning interest in his maps and plans she works her way into his sentry-box, engineering seductive bumps and caresses whenever possible.
When the end of the war forces a lull in their activities, Trim offers to provide some amusement for Toby by telling the story of the King of Bohemia and his seven castles. This tale never really gets off the ground, and Trim digresses instead into the story of how he fell in love during the war. After receiving a wound to the knee, Trim finds himself under the care of a Beguine nun. After a great deal of knee massaging, he suddenly realizes he is in love with her. Toby hijacks the end of the story, which is clearly approaching a sexual climax, by saying, "and then thou...madest a speech."
Widow Wadman, who has been eavesdropping, seizes the passionate pitch of the moment to make a move. She enters the sentry-box and announces that she has a speck of something in her eye, asking Uncle Toby to take a look. Toby at first finds nothing, but as he continues to inspect her beautiful eye, his heart begins to warm to the Widow Wadman. This is the decisive turning point in her campaign.
When Toby informs Trim that he has fallen in love, the two set to work mapping out a strategy. They ready their uniforms and weapons, and Trim decides to attempt a peripheral conquest of Bridget, Mrs. Wadman's servant. The night before the campaign is to take place, Walter writes a letter to Toby full of his brotherly advice about women. The "action" is to begin at eleven o'clock the next morning, and Walter and Mrs. Shandy walk out to watch the drama unfold.