PJ's college gal pal breezes into the Windy City from New York City with her three friends, but they prove to be a flighty, snobby crew. Worse, they seem to be heavily influenced by the "Sex and the City" gang. Meanwhile, Brendan begins to act like an egotistical jerk; and Andy tries to evade his overly friendly neighbor.

PJ's date joins the gang's poker festivities, but he ends up feeling completely neglected. Elsewhere, Andy decides to buy a boat, but there might be nasty ripple effects when he fails to inform his wife about the purchase; and the guys compete over their respective pain thresholds.