He who wins a thousand common hearts, is therefore entitled to some renown; but he who keeps undisputed sway over the heart of a coquette, is indeed a hero.

The narrator sets up the main conflict in the story by describing the rivalry between Ichabod and Brom over Katrina’s heart. He frequently describes Katrina as a coquette in order to show how difficult it will be to win her heart. By casting her as prize, the narrator implies that whoever wins her heart will prove himself to be the better man. This narrative construction foreshadows the ending, implying that the resolution of the story will explain which man Katrina decides to marry.

Just sufficient time had elapsed to enable each story teller to dress up his tale with a little becoming fiction, and in the indistinctness of his recollection, to make himself the hero of every exploit.

In the beginning of the story, the narrator explains that enough time has passed since the American Revolution that fact and fiction have begun to blur into legend, casting doubt on the veracity of the characters. This ambiguity also serves to cast doubt on the authenticity of the narrator himself and creates a mysterious and imaginative tone to the story, allowing for multiple interpretations of the plot and its resolution.

What passed at this interview I will not pretend to say, for in fact I do not know. Something, however, I fear me, must have gone wrong, for he certainly sallied forth, after no very great interval, with an air quite desolate and chapfallen. Oh, these women! these women! Could that girl have been playing off any of her coquettish tricks?

Near the end of the story, the narrator’s speculations about Katrina’s motives as a manipulative ploy to make Brom jealous foreshadow a showdown between the two men. The narrator’s claim that he does not know what happened between Ichabod and Katrina casts doubt on his reliability, in order to leave the ending of the tale open for interpretation. Whether Ichabod leaves Sleepy Hollow out of embarrassment after Brom’s prank or is a victim of the supernatural is meant to be a lingering question.

That there is no situation in life but has its advantages and pleasures—provided we will but take a joke as we find it:

That, therefore, he that runs races with goblin troopers is likely to have rough riding of it.

Ergo, for a country schoolmaster to be refused the hand of a Dutch heiress is a certain step to high preferment in the state.

In the postscript, the storyteller provides three lessons his listeners are meant to take away from the tale. The lessons provided heavily imply the storyteller is an older version of Brom, while the listener is an older version of Ichabod. While all three lessons could be directed entirely at Ichabod, they are also generic enough to be interpreted as overall morals to the story.