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Jordana Spiro portrays Penelope Jane "P.J." Franklin, a sportswriter for the Chicago Sun-Times, the protagonist, first-person narrator, and the core of the group. She becomes a columnist in season 3. In season 4, Bobby moves in with her after he loses his apartment.
Jim Gaffigan portrays Andy Franklin, PJ's brother, whose wife was thought by the gang to keep him on a short leash; however, after she throws him a fabulous birthday party they realize she is a fun woman. Andy admits he likes using his wife as an excuse to go home because sometimes he feels tired and wants to go home, "like an old man." At the beginning of the 4th season, it is revealed that Andy has a new job and has moved to China with his family leaving Mike to safeguard his house until it is sold.
Reid Scott portrays Brendan 'Brando' Dorff, a former hard-rock radio DJ and former roommate of PJ, whose on-again, off-again relationship with his girlfriend often leaves him crashing at PJ's apartment and eventually leads to him moving in with her again. In season 2, he loses his DJ job when the station is bought out by corporate interests. He is usually dressed in a band T-shirt. As of season 3, he is the manager of John's Club, an endeavor that he paired up with John, Bobby's friend whom he meets at Bobby's bachelor party. As of season 4, he has moved out on his own, no longer living with P.J., and in the season 4 finale, now owns Crowley's Bar after buying it to keep it from closing.
Jamie Kaler portrays Mike Callahan, a commitment-challenged ladies' man, and the oldest member of the group turning 43 in season 4. He worked for the Chicago Cubs in season 1 but was laid off. Kenny reluctantly hired him to work at his sports memorabilia store. In season 4 Kenny is forced to shut down the store and Mike gets a job working in the public relations office for the Chicago Bulls. In the 4th-season finale, he marries his girlfriend of one month, Marcia, who lives next door to Andy's old house.
Michael Bunin portrays Kenny Moritorri, a sports memorabilia store owner, who has not mastered the art of dating. He also has a love-hate relationship with Stephanie Layne. At the end of season 3, we see them having a secret relationship. As of season 4, they are openly dating and Kenny is forced to shut down the memorabilia store, starting a closet-organizing service. At the end of season 4, he leaves with Stephanie to London for her new talk-show panelist job in Britain.
Kyle Howard portrays Bobby Newman, a sportswriter for the Chicago Tribune (the rival newspaper in Chicago), he was raised in one of the city's wealthiest families and is a love interest of PJ's. As of season 3, he and P.J. are dating. In mid-season 4, it is revealed that Bobby has lost his money due to his father's bad investments in a Ponzi scheme. He currently lives with P.J. and will begin to attend law school in Chicago.
Kellee Stewart portrays Stephanie Layne, PJ's best friend, who gives her advice on men and dating from a female point of view. Author of a best-selling book about relationships, You're a Great Guy, But.... She also has a love/hate relationship with Kenny Moritorri. At the end of season 3, we see them having a secret relationship. As of season 4, they are openly dating and she has joined the group's poker nights since Andy has moved away. In the 4th-season finale, she is leaving for London with Kenny to start as a panelist on a British talk show.
