The second season finale focuses on Bobby's wedding rehearsal. 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.

The gang head to Bobby's father's ranch for Bobby's wedding. While there, tensions tighten between siblings Bobby and Jack, who woo's PJ. Meanwhile, Mike and an older woman become involved, bobby's father is flirtatious, and a kidney stone fells a member of the wedding party.

Bobby's brother, a reputed womanizer makes romantic advances towards PJ, who deliberates on whether to embrace his overtures or fend him off. Elsewhere, Bobby is rattled by the hectic wedding arrangements, Andy and his wife begin counseling for couples, and Mexican Freddy makes a visit.

The Chi-town boys want to throw Bobby a bachelor party, but can't decide who will be paying for it. Meanwhile, Stephanie's new book steals the headlights when she and PJ attend Elsa's shower, and PJ corners Andy into revealing information on his relationship with Jo.

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.

Andy inspires to become humorous by joining a comedy improv class. Elsewhere, a down Brendan becomes introspective, and looks to become self medicated. Also, Bobby's girlfriend is haunted by visa problems, and Stephanie's book back-cover biography is full of more fiction than facts.

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.

PJ throws a singles dinner party in hopes of finding her Mr. Right. Meanwhile. Stephanie becomes an author when she pens a relationship-themed book. Andy hires a comely nanny with an annoyingly healthy lifestyle.

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.