There is big party to celebrate Caroline's 2000th cartoon strip. However, Caroline has a mental block and is unable to draw anything. Her friends give her plenty of bad suggestions, so she contemplates retirement and trying something else.

Caroline's plans to rent out her house in Wisconsin hit an unexpected snag when Grandma Duffy refuses to leave, forcing Caroline to return to Wisconsin, where she is surprised to learn that her former boyfriend Randy will be her new tenant. Meanwhile, Richard has his hands full in New York when he agrees to take Caroline's place by caring for Annie (who is sick) and Del (who thinks his girlfriend may be cheating on him).