While trying to convince his favorite client, Jeanne Shaw, to undertake a major remodel of her home, Jeff realizes that Jenni is way over her head planning her upcoming wedding in Chicago. Jeff and Jenni fly to the Windy City to nail down the details of her nuptials.

Jeff faces off with a tough new client over budgetary issues while trying to convince her to expand her remodel. Meanwhile the new design assistant, Andrew, finds himself in hot water when he steps over boundaries of inappropriate business behavior.

In the wake of a serious performance review, Andrew desperately tries to prove to Jeff that he's deserving of his job by taking over a project with a tight deadline. As Andrew works to improve his standing in the company, however, Jeff discovers suspicious inconsistencies in his background.