Keenan impersonates Santa Claus at a department store and ends up helping a poor, single mom celebrate Christmas with her children by being 'Santa' for them.
Kenan goes out with a girl who on their date wears her favorite sweater that her grandmother made before she died. During the date, Kel ruins her sweater and he and Kenan try to fix it before she notices.
Inspired by reading Ernest Hemingway, Kenan makes a list of goals to accomplish before he dies, but one of his goals lands he and Kel on top of the Sears Tower and in a lot of trouble.
Kenan writes a lovely poem, inspired by Sharla, for class assignment. Unfortunately, Kel leads a female classmate, Alison, to believe that Kenan wrote the poem for her. When she breaks up with her boyfriend, Kenan and Kel try and make things right.