Icabod leaves the house ''with an air quite desolate and chopfallen.’’ Just prior to this, he has been talking to Katrina, whom he has approached with the plan of asking for her hand in marriage. We can assume from this that Katrina has turned him down, which leaves him feeling so desolate, so dejected.
Ichabod was "heavy hearted and crestfallen" as he left Katrina's house after the party. The author suggests that Katrina had been toying with Ichabod the entire time just to make Brom Bones jealous. The author only asks questions, not stating directly what happened, but his questions point to the idea that Katrina had been playing coquettish tricks rather than being sincere with Ichabod.