PJ Franklin (Jordana Spiro) is a professional sportswriter looking for love within her world, which is dominated by her group of male friends. Her "boys" are her family, which sometimes hinders PJ's dating life, as the men she tries to date don't know how to react to her unconventional interests and the all-important men in her life.
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. Being "one of the guys" can mean a lot of great things: poker games, pick-up softball games, watching sports or just hanging out at a favorite bar. But for PJ being a girl who’s one of the guys can be challenging.
During the first season, many of the episodes involved some of the characters going to match.com, a sponsor of the show, that is often referenced in conversation on the show. The first season seemed to end with a cliffhanger on December 28, 2006. The episode "The Promise of a New Season" aired July 30 and was originally billed as the beginning of the second season. The season had a mere 9 episodes. Later, the first 13 episodes which aired in 2006 were combined with these 9 episodes and the 22 episodes were together released as Season One on DVD. The show had been picked up for a second season with eight episodes, but ended up having 9 episodes. Season 2 premiered on Thursday June 12, 2008. The second season, like the first, ended on a cliffhanger. The third season premiered on Tuesday March 31, 2009, with another set of 9 episodes. The second season cliffhanger is resolved, as Bobby and Elsa break off their engagement, and he admits to P.J. that he had feelings for her. The two date throughout the season, although they try to keep it a secret, to no avail. Meanwhile, Brendan opens the new club with John but quickly finds himself doing all of the work. After pointing out how valuable he is to John, he manages to negotiate a better salary and work schedule. 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.
On October 7, 2008, TBS announced it would run a third season of the show. A new set of nine episodes premiered on March 31, 2009. On September 11, 2009, it was confirmed on TV Guide's website that the show has been picked up for a fourth season, although it would only head back into production in January 2010, with the new season premiering on TBS July 25, 2010.