PJ's dream trip to Italy continues with her mystery date. Back in the Windy City, Brandon fears the changes being made at the radio station, and Andy holds court as a corporate lawyer. And the gang becomes banned from the hangout when Mike sleeps with a waitress from Crowley's.

The boys are on pins and needles when Kenny, Mike, Brendan and Bobby decide to compete in a shirt creation contest. The stakes are high as the prize for the winner is free drinks for a month. Meanwhile, PJ is hoping to write a book about a baseball player, Andy spends long hours at his job, and Brendan wants to learn to become a bartender.