P.J. arbeitet höchst erfolgreich als Sportjournalistin bei einer Zeitung in Chicago. Sie ist in ihrem Beruf fast ausschließlich von Männern umgeben und auch ihr Freundeskreis besteht zum überwiegenden Teil aus Männern. Als der attraktive Bobby Newman in ihr Leben tritt, scheint ein Date mit ihm unumgänglich.

PJ tries to clear things up with Bobby and wants him to know that she is interested, but she also wants to keep their relationship on the down low. She doesn’t realize that she is just confusing things more by using analogies. Meanwhile, Stephanie signs up for Match.com to find a man.

PJ introduces her new acquaintance, Amad, to Stephanie in hopes that they will hit it off. Stephanie is crushed when she learns that Amad is really into PJ and not her. Meanwhile, the fan that Brendan has brought home is driving PJ crazy. The guys find out about PJ and Bobby’s secret one time hook up.

Mike, Kenny und Brendan wollen gemeinsam ausgehen, um mit vereinten Kräften endlich die richtigen Frauen kennenzulernen. P.J. verheimlichen sie ihr Vorhaben aus Angst, sie könne ihnen den Abend verderben. Inzwischen versucht Stephanie, P.J. zu überreden, sich etwas femininer zu geben.

PJ and Hank advance their relationship to the next level when he stays over. The next morning when they are on their way to breakfast, PJ sees Brendan with Wendy. She later confronts him and Brendan tells her he is going to propose. Meanwhile, the guys get on PJ’s case when she opts to hang out with Hank over them.

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.

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.

Zur Überraschung seiner versammelten Freunde taucht Mike eines Abends mit der umwerfenden Traumfrau Dani auf. P.J. ist im Gegensatz zu den Männern nicht gerade erfreut, da sie Dani nicht traut. Außerdem hat P.J. Ärger mit dem legendären Sportreporter Jack Brisco, der ihr eine Topstory über einen Baseball-Superstar klaut.

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.

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.

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.

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.

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.

The kiss that ended last episode seems to not have had any lasting effect as Brendon has moved on to another girlfriend. Kenny also has a new girlfriend who happens to have a bun in the oven. And Andy is getting used to live in the suburbs, including the long commute that comes with it.

P.J. ist als Gast bei einem lokalen Sportsender eingeladen. Sie schlägt den Rat ihrer Freunde, sich auf den Auftritt vorzubereiten, in den Wind und bekommt auch prompt die Rechnung dafür präsentiert.

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.

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.

Thorn, a war correspondent and a former flame of PJ’s, is coming through town. Mike convinces Kenny to let him help out in his store. Stephanie is going to debt counseling, but her counselor Lance is torturing her. Brendan is trying to keep his options open.

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.

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 subjects her new love interest, Evan, to a game of poker with the gang. Andy decides to buy a boat without telling his wife, Meredith. Kenny, Mike, Brendan and the rest of the gang try to one-up each other by comparing pain thresholds.

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.

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.

PJ throws a singles dinner party in hopes of finding her Mr. Right. Stephanie becomes an author when she pens a relationship-themed book. Andy and Meredith hire a nanny, Elsa, who happens to be hot and from Sweden, and the boys hold nothing back in their competition to impress her.

PJ lands a job ghost writing for a famous athlete but finds it a difficult task when the athlete becomes more than she can handle. Meanwhile, Brendan dives deeper into depression when he runs into his ex, Wendy, who is happily pregnant and in a relationship.