The identity of PJ's mystery man surprises Stephanie. Stephanie quickly dampens their vacaction. Back in Chicago, the boys are experiences changes in their professional and social lives, only some of which are for the better.

Stephanie wants to have a dinner party to meet new men. Stephanie also has a book that she wrote get published. Andy hires a new nanny who is very good-looking. She has a habit or two that Andy doesn't enjoy, but one of the other guys doesn't mind at all.

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 takes an improv-comedy class. Brendan indulges in self-medication because his life isn't going so well. Bobby and his girlfriend have some issues to deal with.

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.

Bobby's brother, Jack, shows up for Bobby's party and takes and interest in P.J. Stephanie meets a man named Warren at a bar and they strike up an informative conversation.

PJ wonders whether to pursue the romantic advances of Bobby's brother, Jack. Meanwhile, arrangements for the upcoming wedding rattle groom-to-be Bobby. Andy and Meredith attend couples counseling. Also, Kenny runs into Mexican Freddy (David Pressman) again.

PJ and the gang head out to California for the weekend to attend Bobby's destination wedding. At the ranch of Bobby's father, PJ tries to hide her relationship with Jack from Bobby, whilst sibling tensions arise between the two brothers. Meanwhile, Mike meets an older woman.

Bobby reveals his choice for a "best men" and Mike makes discoveries about Maggie. Meanwhile, PJ hopes to repair the damage between Bobby and Jack, and PJ and her boys discuss how the status quo will be upset by Bobby's marriage.