The fifth season begins with Jane desperately searching for Owen, who disappeared just before their wedding. Luke tells Jane that "Old Jane" is back on Earth and could be in anyone's body. Meanwhile, Jane takes a case involving a boy whose drug treatment is terminated by a pharmaceutical company; and Kim represents a woman whose ex-boyfriend posted nude photos of her on the Internet.
Jane works with "Old Jane," who is now in the body of a sexy model. Together, they defend a death-row inmate convicted of killing a former classmate. Meanwhile, Grayson and Kim represent a mattress salesman who claims he was wrongfully terminated for dressing like a drag queen.
Jane represents a jilted bride who is suing the former groom for damages; a surrogate mother searches for the missing parents of the child she is about to deliver; Stacy seeks advice from business mogul Barbara Corcoran; Kim introduces a new partner at the firm.
Jane enlists Paul to watch Stacy when her demeanor changes. At work, Owen helps her out with an SAT cheating case. Greyson and Kim tackle a case of "Dog acting accordingly" when a pampered pup ends up pregnant.
Kim takes on an alimony case close to home. Owen hires an assistant who eyes Greyson. Teri and Stacy talk sperm donors. And Jane defends a high-profile baseball player in a homicide case.
Owen and Jane team up to tackle the case of a professor accused of smuggling drugs, and Jane uses it as a platform to pull Owen back into her life. A female video game designer goes to court for credit when it's given to her dead boyfriend. Stacy delves into her ex's pool for a possible father to her future children.
A pageant contestant is stripped of her crown after claiming the Miss Universal Globe competition is rigged. Meanwhile, Kim represents her estranged dad when he loses his coaching job; and Stacy tries to convince Jane that Owen is an ideal sperm donor.
Following a long night at a bachelorette party, Jane ends up at the U.S./Mexico border to defend the bride's fiance, whose bachelor party went south of the border. Jane must get the groom back into the U.S. in time for the wedding. Kim represents a housewife who claims that her online erotic novel has been plagiarized by a major publisher. Meanwhile, a mysterious man appears at the firm, yet his motives remain unclear to the lawyers of Harrison & Parker. Owen struggles with his new role as Stacy's sperm donor.
Jane defends a troubled socialite and through a series of unfortunate legal turns puts the future of the firm in jeopardy. Meanwhile, Grayson represents a man who was thrown off of a commercial flight for claiming to be a vampire; and Owen shares some tough news with Stacy.
A woman files a personal-injury lawsuit when she is hurt during a wife-swap exercise as part of couples' therapy group. Meanwhile, Paul sets Jane up on a blind date; Stacy and Owen question their feelings for one another; and a man who incorporated himself hires Grayson and Owen when his shareholders try to prevent him from marrying the woman he loves.
Jane defends a woman in witness protection who was caught in the middle of a drug bust; Owen represents a teen star whose reputation is put at risk after a risqué photo is taken of her; a man hires Grayson to draft an unusual love contract between him and his new wife.
Jane represents Deb's mother in a scandalous case involving sex solicitation; Grayson visits Wyoming where he must try a California client's case under Wyoming law; Nicole and Grayson's relationship takes a turn; Stacy is humiliated at yoga class.
Season 5 concludes with Jane representing an Amish farmer in a case against a big oil company. Meanwhile, Grayson helps a dominatrix try to collect a debt from one of her clients; and Grayson and Jane reveal their feelings for one other but are overheard by an unexpected visitor who threatens to tell everything.