One of Ichabod’s singing students is Katrina Van Tassel, an eighteen-year-old known for her beauty and her wealth. She is the daughter of a very rich farmer, which gives her many suitors. Ichabod, already taken in by Katrina’s womanly charms, falls for her completely when he sees her father’s abundant farmland, animals, and spacious farmhouse. He decides he must have her.
Among Ichabod’s rivals, Brom Bones is his greatest threat. Brom is a rowdy and boisterous troublemaker, known throughout the country for his heroics and feats of strength. He is liked and respected by almost all. Although he is mischievous, his basic kindness makes him easy to like. Brom has singled out Katrina for his attentions, and most of the other rivals have already fallen away, not daring to cross his path.
Ichabod is not, however, dissuaded by Brom’s formidable presence, although he does make his overtures much more subtly and insinuatingly than he otherwise would, so as not to disturb Brom too much. He comes to Katrina’s house repeatedly under the guise of his role as her singing teacher, and he woos her under her parents’ not very watchful eyes.
Katrina, being a coquette, returns both Brom’s and Ichabod’s interest, and a powerful feud quickly develops between the two suitors. Brom, not surprisingly, would like to settle this in a physical contest, but Ichabod is too aware of his shortcomings in that area to do so. This issue frustrates Brom, who instead turns to practical jokes and doing his best to humiliate Ichabod in front of Katrina.
This conflict continues on for some time with no real winner. One day, while Ichabod is teaching, a messenger from the Van Tassels comes to invite him to a party at their farm that evening. He finishes the day’s lessons as quickly as he can and sends the students home early so that he can start preparing for the party. He puts on his only suit, borrows a horse from the farmer he is staying with, and heads to the Van Tassels’ farm. The horse, Gunpowder, is an old and quite broken down plough horse, but still vicious enough.
Ichabod arrives at the party, where there are many farmers and farmers’ wives. Brom Bones has arrived on his dangerous horse Daredevil. Ichabod is immediately drawn in by the abundant cakes, pastries, and dishes, and he spends his time characteristically eating all he wants. He then has a wonderful time dancing—another skill he prides himself on—with Katrina. He is in ecstasy while Brom looks on jealously.
After the dance ends Ichabod goes over to where some of the older men are smoking and telling war stories—all of which are far enough in the past to be safely exaggerated. They then move to ghost stories, covering many of the local legends and continually returning to the favorite: the tales of the Headless Horseman. Brom Bones tells a story of the time he encountered the Headless Horseman and offered to race him for a bowl of punch. Ichabod listens closely to all the stories and adds a few of his own.
The crux of the story emerges in this section—the love triangle between Ichabod Crane, Katrina Van Tassel, and Brom Bones. It quickly becomes clear that Ichabod’s love is far from pure. Although he is attracted by Katrina’s pretty youth and flirtatiousness, it is not until he sees her father’s property that he truly considers himself in love with her. The other suitors probably feel the same way. After all, Katrina is a fairly flat character, not really more than the stereotypical farmer’s daughter. Irving is using a traditional plot line, the suitor disguised as a teacher, and the real literary interest here is not the plot or the characterization of Katrina but the rivalry between two very different lifestyles. Brom is a man of action, a successful one at that, but Ichabod is a man of letters, a barely successful one, and despite his other skills, he is not much more. He is bold when he carries the rod against the strongest children, and he lets himself think he has other great skills, such as singing and dancing. In reality, Brom Bones has all the social and athletic success. The differences between the two men ultimately are judged by Katrina.
Katrina and her father’s farm blur together, both in Ichabod’s perception of her and in the reader’s, for Katrina is commoditized by the suitors. She is a young, attractive coquette, which the narrator describes as a shifting cipher. Her value apparently lies in her inheritance, and the narrative goes on for pages describing all of her father’s lands, his animals, his house, and its decorations. Thus Katrina becomes a means to the end of wealth. Ichabod does imagine a life with her, but in his mind she is the bearer of his children rather than some kind of equal partner in marriage.
Ichabod’s confidence in his one suit is a bit pathetic. He would be unlikely to be able to provide support for his wife; he would need to rely on Katrina’s wealth. He is something like a parasite in his constant desire to consume. He does nothing to produce material wealth, and the townspeople do not much value unproductive skills like thinking (this is a sign of the stereotypical American anti-intellectualism of a sleepy country town) or singing and dancing. His desires are so enflamed by the bounteous resources of the Van Tassel farm, and his fantasies of being its owner are so strong, that he loses all sense of probability, considering himself practically to have won Katrina’s hand already.
Ichabod’s distance from reality is also underscored in his rivalry with Brom. The reader sees Brom grow frustrated and jealous as Ichabod spends time with Katrina, but we never see Ichabod’s reaction to Brom’s suit except avoidance. Indeed, even once Brom starts to play pranks on Ichabod, we never see Ichabod react at all—he is too busy fantasizing about being master of the Van Tassel farm to deal with the realities of obtaining his objective. Brom has a strategy that is working, though as the town darling, he does not need to do much other than be himself. In contrast, Ichbod is still an outsider so far as the townspeople are concerned.
The absurdity of Ichabod’s character is also highlighted further in this section. He excitedly sends his students home from school early so that he can prepare for the party, and he borrows a horse so that he can arrive in style. Even so, he looks absurd on the broken-down horse he rides, for which his legs are much too long. Try as he might, he cannot escape his own comedic look. He is more likely to be the butt of a joke or the target of a story than to be the creator of his own story. He does his best to control his circumstances, but he does not have the grasp of reality or the skills or the wealth to do so.