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.

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.