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 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.
Kenan and Kel suspect Roger is Chicago's notorious Diamond Bandit after seeing the crook (who bears much resemblance to Roger) on TV; and think their suspicions are correct when they find diamonds hidden in the couch, unaware that they're cubic zirconium samples Roger's looking at for a present for Sheryl.
Kel comes down with the common cold and Kenan tries and succeeds in inventing a cure for it. When Roger gets Kel's cold, they make a new batch for him to take to work at the airport, but the new batch doesn't cure the cold, it puts people to sleep.
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.
When Kenan's parents are away for the weekend and Kenan and Kel are in charge of the house, Roger's pet cockatoo, Twizzles dies and Kenan and Kel try to replace it before his parents get home.
