The kiss between PJ and Brendan last year still causes tension between the two but seems to not have had any lasting effect as Brandon has moved on to another girlfriend. Kenny also has a new girlfriend, Kimmie, who is pregnant. And Andy is getting used to life in the suburbs, including the long commute that comes with it.
PJ is invited to appear as a guest on a local cable sports show, while Stephanie tries to convince her to go on a trip to Italy in October with the boyfriends they hope to find by then. Andy tries to find a solution to his commuting issues on poker night.
Brendon 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.
Stephanie runs into money problems after accumulating quite a bit of debt, but accountant Andy is coming to the rescue. Meanwhile, 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. And Kenny's new girlfriend is a bit mysterious.
PJ's old boyfriend from college come to Chicago. Mike is hired by Kenny to work at his sports shop. Brendon is still acting like a jerk since he made the "Sexiest Bachelors of Chicago" list.
PJ's first editor from her college newspaper comes to town with three close friends in tow. Brendan has a new friend who is completely obnoxious and condescending. Stephanie is starting to find herself smitten by Lance, her debt counselor. Mike makes a bizarre purchase for Kenny's store. And Andy has a new neighbor who seems way too nice.
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. Brendan, Kenny and Mike desperately pursue a young single mom while PJ meets a nice young man from the city.
Stephanie expresses her concern to PJ when she subjects her new love interest, Evan, to a game of poker with the gang, a game during which Evan feels completely invisible. Meanwhile, Andy decides to buy a boat to placate his feelings of not being able to have a place to himself. Unfortunately, however, he decides not to tell his wife, Meredith, about the purchase. And Kenny, Mike, Brendan and the rest of the gang try to o…more
Italy is just days away, and PJ still doesn’t have a date. But it isn’t for lack of opportunities, as three of the men in her life make welcome but untimely returns, including botanist Evan, globe-trotting reporter Thorn Packer and Cubs player Matt Dougan. Meanwhile, the gang decides to be tourists in their hometown taking in all the Chicago sites they’ve never seen, such as the Art Institute and the Sears Tower. P.…more
Bobby experiences cold feet on his wedding day. P.J. gets caught in a difficult situation between Bobby and his brother.
Keeping her new boyfriend a secret from her friends proves difficult for PJ. Brendan opens a nightclub. Mike finds good reasons to keep his moustache.
PJ gets her own column in the paper but the guys think that it may be because of her looks rather than her writing. Meanwhile, Brendan brings Kenny to a new, exciting club.
As the gang's annual board game decathlon approaches, Bobby accuses PJ of being too competitive. Stephanie uses the guys as research for an article she is writing.
After getting into an accident on his new scooter, Brendan lets PJ make all of his decisions for a week. Kenny's band needs a new bass player.
PJ and Bobby's picnic in the park becomes an important life decision. Kenny jumps into a new relationship.
The gang discusses the pros and cons of Facebook. Bobby realizes that PJ stays in touch with all of her exes.
PJ hits it off with one of Stephanie's friends. Kenny and Mike introduce a new friend to the group.
The gang heads to Arizona for spring training. PJ looks for a unique topic to write about in her column.
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