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.

Andy tries to prove a rumor is false in which he is having an affair with a coworker. Elsewhere, Bobby's family is making a disaster of the wedding plans; Kenny's winning streak when it comes to romance continues; Brendan works as a temp at a mail room; and Stephanie's new book includes references of the gang.