Into female sports columnist PJ's close all-male circle of serious baseball fan friends comes Bobby, a rival columnist who fits right in. Stephanie (PJ's only female friend) delights in tomboyish PJ considering him for romance.
The whole gang is in a dating slump, which PJ makes worse when she tags along with the guys to a singles' bar. Afterwards, Stephanie drags her on a "ladies' evening" to help her get in touch with her feminine side.
Kenny's friend Trouty (whom the guys don't like and regard as a bad hang) joins the poker game. Meanwhile, PJ gets the guys to hang out with Hank in return for agreeing to spend a day with Wendy.
PJ is forced to choose between going to dinner with her new boyfriend or competing with the guys in the annual decathlon competition they cooked up several years before.
Three superstars enter PJ's life: foxy lady Dani (on Mike's arm, no less), surly veteran baseball player Hernando Garcia, and renowned reporter Jack Brisco - all at some point giving PJ a bad vibe.
When Aunt Phyllis (PJ's idol) comes to town, PJ's enthusiasm cools when the woman begins dating one of her guys. Bobby is far less enthusiastic about meeting one of Mike's baseball idols, a very self-centered has-been.
PJ, against Stephanie's advice, agrees to go out with a former classmate, while Bobby follows some bad advice on how to handle some inside information about Mike.
PJ's kiss with Brendan falls flat as he moves on to a new girlfriend, Kenny sparks to a pregnant girl, and a boring commute from the suburbs begins to wear on Andy.
PJ gets flustered over her appearance on a local cable sports show, while Stephanie hatches a plan for them to take their boyfriends to Italy. Only trouble is, they don't have boyfriends yet.
Andy gives Stephanie financial advice, the gang finds out Bobby's financial situation, and Kenny finds a new way to hit on women - no matter what the cost is.
P.J.'s boyfriend from college comes to Chicago, rekindling old feelings in her, Kenny hires Mike to work in his shop, and Brendan avoids his girlfriend.
Brendan's ego gets out-of-hand that the gang decides to hold a douchebag intervention. Meanwhile, PJ's college friend Lyssa and her all-things-New-York entourage descend upon Chicago while Andy suffers from an overly friendly neighbor.
The gang heads out to the Hoffman Estates for a barbecue at Andy's house. P.J. runs into a botanist. Mike, Kenny and Brendan compete for the attention of a single mom. Andy receives some shocking news.
As a reaction to his impending fatherhood and status in life, Andy buys a boat without telling Meredith. P.J. brings Evan to the poker game, and the guys argue about who's manliest.
