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 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.

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.

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.

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 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.

Kenny begins to date two women and this drives Mike insane. Andy decides to set Mike up with his work wife, Jo, in hopes to boost his mojo but learns she's only interested in Andy. Brendan takes a temp job at Andy's law firm and the guys read Stephanie's book only to discover she's used them as source material.

When P.J. gets her own column in the paper, the guys tease her that she got the promotion because of her looks; Andy gives Bobby much-needed advice about women.