P.J.'s a single gal whose friends are a bunch of guys. In the pilot, she becomes instantly attracted to a friend of a friend and invites him to play for her softball team. Meanwhile, her "good friend" Brendan confesses to the group that he is single once and for all after ending things with his on again, off again relationship.
P.J. confuses Bobby with all her baseball metaphors concerning their budding relationship, which she prefers to keep discrete. He gives her a signed baseball as a gift, but she is confused herself when he begins to date a yoga instructor soon after. Meanwhile, Mike goes after a woman Kenny's too passive to pursue.
P.J. tries to set up her best friend with a new guy in the group, but her magnificent plan goes awry thanks in large part to Brendan's latest bedroom partner: a comely lass who's a brand new fan of his radio show.
P.J. meets a well-mannered, respectable, even dignified, professional guy but fears her blue collar boys will ruin her shot with him.
P.J. and Hank become more intimate, and their time together begins to interfere with her time with the boys. But when she spies Brendan with Wendy, she decides to spend some time with him to figure out what he's doing with his ex and discovers he plans to propose to her.
P.J.'s attempts to indoctrinate her boyfriend into the poker game doesn't go too well, nor does Kenny's new addition named Trouty. When she tries to get the boys to hang out with her new beau, she's compelled to make a parallel agreement and spend some time with Wendy, Brendan's on-again girlfriend.
P.J. begins to question her relationship with Hank after she opts out of the group's annual decathlon, a night of drinking and games. Part of her problem is that Hank doesn't really gel with the boys and the other part is that she finds herself more and more attracted to Bobby, especially after a work trip winds up with them sleeping together. So, P.J. decides to break up with Hank and become a "free agent."
P.J. tries to get an exclusive interview with the Cubs' big free agent acquisition but finds the task to be problematic. Meanwhile, she must deal with a legendary sports reporter plagiarizing her; Mike dates a ridiculously attractive woman of whom P.J. is suspicious until the woman helps her get an interview with Garcia. But then, the woman dumps Mike for another athlete, thus confirming P.J.'s suspicions.
When Andy's wife Meredith goes out of town, PJ sees it as an opportunity to nudge him to let loose. Unfortunately, the emergence of Fun Andy could spell the end of the group's fun period. They all learn very quickly how important Meredith is to reigning in Andy.
The gang gets into an exclusive club called The Streisand, thanks to Trouty's friendship with the owner, Steve. But when Steve takes an interest in PJ, the boys see it as an opportunity to get in close with the owner themselves, circumventing the obnoxious Trouty.
PJ's hero, her aunt Phyllis, surprises her in Chicago. PJ's image of her is tarnished when Phyllis hooks up with Kenny but then ditches him. Meanwhile, Mike meets his idol, a former Cubs pitcher named Danny Finn. But his image of Finn is tarnished when Finn reveals himself to be a huge jerk. Meanwhile, Brendan and Wendy call off the wedding.
PJ's mercy date with an old buddy from college doesn't end well when she finds it hard to lose the guy. Meanwhile, Mike's pride is hurt when he's fired, but he's more upset by the fact that his friends knew about it in advance and failed to warn him. And, in order for Brendan to more quickly get over his split with Wendy, he decides to give up alcohol.
PJ and Brendan's relationship becomes complicated after she tells the boys about the time they made out in college. Meanwhile, PJ and the boys surprise Andy on his birthday with a trip to Wrigley Field, where they get to play a game on the field all by themselves; Andy's tales of woe regarding Meredith aren't exactly true; and, Brendan confesses to PJ that he had feelings for her in college, and then they kiss.
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.
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.