The fifth season premiered on January 6, 2008, with episode LGB Tease.
Eva "Papi" Torres (Janina Gavankar), and Dallas Roberts' male token character Angus Patridge were both written out.
Sweeney starts the process of transitioning switching his name to Max.
Erin Daniels' character Dana Fairbanks starts in a multi-episode storyline dealing with a breast cancer battle and culminating with her death.
Besides Chaiken, writers of the show have included Guinevere Turner (Go Fish, American Psycho), Susan Miller (Anyone But Me, Thirtysomething), Cherien Dabis (Amreeka), and Rose Troche (Go Fish, Six Feet Under). The original six-year run ended with the series finale's airing on March 8, 2009.
Tina begins seeing Helena, while Bette’s life is portrayed as a wreck, with alcohol abuse, problems with her job, the death of her father in episode 2.12: L'Chaim, and being fired during the season finale. The character of Marina was written out of the show, and the Planet was bought by Kit Porter.On July 11, 2017, it was announced a sequel season was in the works with Showtime.Other executive producers include Steve Golin (Being John Malkovich, Eternal Sunshine of the Spotless Mind) and Larry Kennar (Barbershop).Notable of this season is that each episode begins with a short pre-credits vignette of two individuals meeting romantically or sexually.As the season progresses, lines from Alice's chart (see below) connect one member of each vignette with a new individual in the next.Clementine Ford, reprised her role as Phyllis Kroll's daughter and began a relationship with Shane Mc Cutcheon.Drew played Adele, a young fan of Jenny's work who gets hired as her personal assistant.Marina relentlessly pursues Jenny and succeeds in destroying her relationship with Tim.The season also introduces Shane Mc Cutcheon, an androgynous, highly sexual hairstylist and serial heart-breaker; Alice Pieszecki, a girly, bisexual journalist looking for love in any way she can, and Dana Fairbanks, a professional tennis player who is still in the closet and torn between pursuing her career and finding love.It begins six months after the birth of Tina and Bette's daughter, Angelica.New characters in this season include Moira Sweeney (a working class butch portrayed by Daniela Sea who is Jenny’s girlfriend for most of the season) and Angus Partridge (portrayed by Dallas Roberts), Angelica’s male nanny who later becomes Kit's lover.