When Grace receives an unexpected marriage proposal from her boyfriend, Will tries to be supportive of her decision but finally tells her that she's making a mistake, even though he's putting their friendship at risk. The situation is complicated by interference from Grace's socialite assistant, Karen, and Will's outrageous friend, Jack.

Grace blames her relationship with Will as the reason for her lack of interest in dating and decides they can no longer have fun together. Meanwhile, Jack enlists Will's help when the IRS catches up with him.