One of the most formidable elements that makes it difficult for Ichabod to marry Katrina would be Brom Bones. Crane's most significant challenge in courting Katrina represents everything that Ichabod is not. Brom Bones is assertive, strong, and carries a personality that makes him the diametric opposite of Crane. Crane is cerebral and passes for an intellectual because he has ‘‘read several books quite through." This is fundamentally different than most in the town. Bones is able to capture the fancy of Katrina because of his charm and his reputation. Brom is imposing and demands a sense of immediate respect. Certainly, Katrina does respect Ichabod, but "not like that." The presence of Brom Bones as someone that demonstrates himself to be the opposite of Crane is one reason why he finds it difficult of capturing the fancy and attention of Katrina.
At the same time, Crane is not the type of person that Katrina would find interesting to marry. In a sense, she is out of his league. While he is her singing teacher, Crane believes that he can win her over because she is a "bit of a coquette." Yet, this is the precise reason why Crane finds difficulty in trying to marry her. She is the type of girl that is not going find Crane's attributes very appealing. While Ichabod might be able to tell a good ghost story and is one who she respects, Katrina is not shown as someone who will immediately find the qualities of the school teacher to be all that appealing. Katrina's ability to be more discerning and selective comes from wealth and the status that it affords her. Crane is a school teacher, reflective of an economic condition that is different than Katrina's. Crane is not really going to be able to bridge the difference between both worlds. Crane covets Katrina's hand in marriage as a response to such an economic condition. When he leaves her that night 'with an air quite desolate and chopfallen," this reality might have hit him. This reality is one other reason why Crane finds challenge in trying to marry Katrina.