Ichabod Crane first met Katrina van Tassel when she came to the weekly singing lessons he gave for the interested townspeople. She was by far his favorite of his "musical disciples" because of her father's great wealth. As the only child of the wealthy Mynheer Van Tassel, she stood to inherit his farm and his worldly goods. Being very interested in her for these reasons, Ichabod contrived to give her music lessons at her own home so that he could view the potential fortune first-hand; therefore, "under cover of his character of singing-master, he made frequent visits at the farmhouse." While there, he courted her beside the spring and took walks with her at twilight. 

Brom Bones could have easily disposed of his rival Ichabod in hand-to-hand combat, but Ichabod made sure he was never in a situation where Brom could carry out such a demonstration of his physical dominance. Therefore, Brom was reduced to getting revenge on Ichabod by playing practical jokes on him with his buddies. They stopped up the chimney of the place where he was giving music lessons, went into the schoolhouse at night and turned all the desks upside-down, and trained a dog to howl outside the window when Ichabod was giving singing lessons.

When both Ichabod and Brom are invited to the Van Tassel's for a "quilting frolic," Brom hatches his plan for the ultimate practical joke. As men are sharing ghost stories, especially tales about the Headless Horseman, Brom adds his own frightening account of having met the Hessian phantom and winning a race against him before he vanished into thin air. On Ichabod's eerie ride home that night, he is followed by a frightening figure on horseback that throws its head at him. Ichabod disappears, never to be seen again, leaving only a shattered pumpkin as a sign of where he might have encountered the Hessian. Brom then marries Katrina. The special pleasure Brom takes whenever the story is told of Ichabod's disappearance, especially his hearty laughter "at the mention of the pumpkin," leads some people in the town "to suspect that he knew more about the matter than he chose to tell." In other words, Brom's final practical joke by which he took revenge on Ichabod for stealing Katrina was to masquerade as the Headless Horseman and to frighten Ichabod away by throwing a pumpkin at him. 

Ichabod Crane would visit the Van Tassel home with the excuse that he was there as "singing-master" for Katrina. He wasn't afraid that her parents would disapprove but that Brom Bones, who also liked Katrina, would beat him up. Brom, however, did not resort to physical violence (probably because Crane was a weakling), but used practical jokes instead. Brom and some friends "smoked out the schoolhouse" by stopping the chimney, broke into the schoolhouse at night and turned everything upside down, and taught a dog to howl every time Crane began to sing. Of course, there is the Headless Horseman, who was probably Brom, but that is never confirmed.