The show deals with a sports columnist in Chicago, Illinois, played by Jordana Spiro, and the men in her life, including her brother and her best friend.

[1] PJ Franklin (Jordana Spiro) is a professional sportswriter looking for love within her world dominated by her group of male friends.

Her tomboyish, upfront approach to relationships tends to intimidate potential suitors, which leads her only female friend to advise her to dress and act more feminine.

Scenes took place in the Art Institute of Chicago, Northerly Island, the skydeck of the Sears Tower, and Wrigley Field.

He also realizes his pattern of dating mentally unstable women, such as the one in "Carpe Burritoem", has to stop; a point emphasized by the crazy "girlfriend" of Chicago Cubs player Mike Fontenot, who makes a cameo appearance in the season 3 finale.

At the end of the season, it is revealed that not only did Kenny and Stephanie continue to secretly date after their night in Arizona, they are in love.