PJ’s college newspaper editor comes to town with three close friends in tow. Brendan has a new friend who has some unique traits that Brendan is starting to display himself. Stephanie is smitten by her debt counselor. Mike makes a bizarre purchase for Kenny’s store.

Trouty takes everyone to a super exclusive club, The Streisand, to hang out. Turns out Trouty is a welcomed guest of the club and is tight with its owner, Steve. PJ finds herself enamored with Steve until she realizes he is a typical jerk and Trouty comes to her rescue. When the guys talk badly about Trouty, Steve overhears and throws them out of the club.

When PJ tells the guys that she and Brendan made out back in college, things start to get weird between them. Meredith wants to throw Andy a surprise birthday party and asks PJ to keep him busy the day of so she can prepare. PJ and the gang surprise him when they take him to Wrigley Field. PJ realizes the horror stories Andy has been telling about Meredith aren’t true. And Brendan admits that he had feelings for PJ back in college. They sort things out and then he surprises her with a kiss.

Bobby experiences cold feet on his wedding day; P.J. gets caught in a difficult situation between Bobby and his brother (Billy Burke); Andy's new baby.

Keeping her new boyfriend a secret from her friends proves difficult for P.J.; Brendan opens a nightclub; Mike finds good reasons to keep his moustache.

PJ, Bobby, Kenny and Stephanie go out to a nice dinner like adults.

Bobby takes exception to PJ's competitive nature during the annual gaming decathlon. Meanwhile, Stephanie uses the guys to research a new article she is writing.

Brandon is chosen as one of Chicago’s Top 50 Sexiest Bachelors while PJ contemplates an ethically questionable relationship with the new Cubs pitcher. And Trouty makes an appearance in an unexpected place.

The gang head to Arizona to watch some spring training baseball. P.J. writes about the beginning of baseball season in order to keep all her bases loaded, but comes down with a case of writer's block. Meanwhile, Brendan has caught the eye of a player's girlfriend, and a lonely Andy remains back in Chicago.

Crowley's is being taken over by college graduates and the gang decides to find a new bar.

PJ and Andy’s Aunt Phyllis visits Chicago for the weekend. PJ is thrilled because Phyllis is her hero. Things get a little weird for her when Phyllis and Kenny hook up. PJ doesn’t want Kenny to get hurt so she asks Phyllis to make sure they are on the same page. But Phyllis takes off before doing so, leaving both Kenny and PJ very disappointed. Meanwhile Mike meets his idol, baseball legend Danny Finn, who later turns out to be a jerk. Brendan and Wendy call off their wedding.

Mike recruits the gang to help with planning Marcia's birthday party.

PJ can’t do the annual decathlon, a night of competitive games, because she already has plans with Hank. Andy takes her spot. PJ is slowly starting to feel like Hank may not be the best match for her because he doesn’t mesh well with her friends. PJ and Bobby travel for work and find themselves in a confusing situation when they sleep together. PJ breaks up with Hank.

Stephanie runs into money problems, but accountant Andy is coming to the rescue. The gang learns a big secret about Bobby that changes their entire perspective on him. Mike is taking a yoga class in an upscale neighborhood, but his mind isn’t exactly on fitness.

Italy is just days away, and PJ still doesn’t have a date. The gang decides to be tourists in their hometown. Andy has some surprising, life-changing news involving his new boat, his pregnant wife and their house in the suburbs.

Jack cannot be found on the day of the wedding rehearsal; P.J. is determined to set things right between the Newman brothers; Kenny and Stephanie try to keep a secret.

Bobby is considering a new career; Brendan decides it's time to move out of PJ's.

PJ and Stephanie decide to intervene with Mike and Brendan's dates.

PJ is excited when Meredith goes out of town for the weekend and Andy decides to let loose. He goes into “fun Andy” mode and is partying and drinking non stop. PJ quickly gets tired of “fun Andy” and realizes how essential Meredith’s leash on Andy is.

PJ goes on a ‘mercy’ date with old college buddy Keith and then can’t get rid of him. Bobby tells Kenny that Mike is going to get fired and agree not to tell Mike to protect his pride. Mike ends up getting fired and learns that Bobby knew in advance and gets upset with him. Meanwhile, Brendan is trying to get over Wendy by giving up alcohol.

Andy invites the gang to come to a housewarming barbecue at his new digs in the suburbs. Once they arrive, PJ realizes her brother’s home is identical in every way to their home when they were kids. Also attending the barbecue are PJ and Andy’s parents: Eileen, their intrusive mother who spoils a big surprise, and Frank, whom Andy is convinced is the future version of himself. Brendan, Kenny and Mike desperately pursue a young single mom while PJ meets a nice young man from the city.

Stephanie's shocked to see who PJ's mystery man is, and it doesn't take her long to get in PJ's business, making the trip a little less romantic. Back in Chicago, the boys are experiences changes in their professional and social lives, only some of which are for the better.

Spring fever hits the Windy City as springlike warmth during the middle of winter prompts PJ and Bobby to hold a picnic in the park...but a crucial life decision complicates the outing. Meanwhile, Kenny begins a new relationship, and Mike tries vainly to emulate actor Mathew McConaughey by buying a dog and a Jeep.

PJ and the guys look for a replacement for Andy, while reminiscing about how they all first met.

Trouty, Kenny’s friend, joins the poker game. The guys don’t like Trouty and think he’s a bad hang. Meanwhile, PJ tries to get the guys to hang out with Hank. In return, PJ agrees to spend some time with Wendy.