Cuando Brian le pide a Ally que vivan juntos, a ésta le asaltan muchas dudas sobre su futuro. Resulta que no se siente satisfecha sexualmente con él. Acude a la consulta de Tracy, su terapeuta y allí se encuentra con Larry Paul (Robert Downey Jr.) desempaquetando cajas. Ally se siente muy atraída por él. Por su parte, John representa a una amiga que quiere anular su matrimonio por vicio del consentimiento porque ha sorprendido a su marido en la piscina con una modelo. Arguye que él contrajo matrimonio con intención de divorciarse posteriormente de ella para obtener una sustanciosa compensación económica. Ella está abatida porque se siente incapaz de atraer a hombre alguno. John le pide a Richard que la corteje para animarla.

Ally funda con Renée, Elaine, Ling, Nelle y Georgia una asociación de mujeres para tomar el control de sus vidas amorosas, ser eficaces en conocer hombres honestos y libres y encontrar un compañero para compartir la vida con él. Consultando con Mark, este le dice que los hombres prefieren a las modelos porque son bellas, altas, sofisticadas, no hablan mucho y están acostumbradas a obedecer. Las chicas organizan en el bar una “noche de las modelos”. Las modelos nunca acuden a ese tipo de fiestas porque no quieren competir entre ellas por lo que las chicas tienen a todos los hombres para ellas. Acuden también Brian y Larry. Fish y Ling llevan el caso de Cindy, (Lisa Edelstein) una joven con un sorprendente secreto que fue despedida por negarse a pasar un examen médico. Alegan que dicho examen médico obligatorio constituye una violación del derecho a la intimidad personal. John y Nelle se enfrentan a Renée y Georgia en el tribunal. Defienden a una arquitecto, llamada Mayra, (Marcia Cross) demandada de acoso sexual por un empleado suyo. John se siente atraído por ella y el sentimiento es recíproco. Por su parte, Mark se siente atraído por Cindy, la cliente de Fish y de Ling, y hace todo lo que está en su mano para ligar con ella.

Mark's girlfriend finally reveals "her" secret; Ling and Nelle represent a woman suing a relationship guru whose advice ruined the woman's marriage; Ally is dating two different men who end up being related.

Ally runs into Kimmie Bishop, an old friend of hers from college. Ally makes fun of her in front of her fellow puritan friends, and Kimmie is so outraged she decides to sue Ally for defamation. Instead of having someone from the office to defend her, Ally hires therapist/lawyer Larry Paul. When Renee tells her he's married, Ally freaks. At the bar, while trying to decide if she would date a father or a son, she sees Larry with Nelle. Turns out he's divorced, and so Larry dumps Nelle to go out with Ally. Meanwhile, Mark is having a hard time at the office because nobody approves his relationship with Cindy, so he breaks up with her.

Kimmie comes to Cage & Fish looking to hire Ally. She's suing her old firm for wrongful termination. They fired her for being too puritan, and the opposite lawyer is Larry. Now Ally and Larry have to face each other in court. Meanwhile, Ally is nervous about her first kiss with Larry and seeks for advice with Ling, who demonstrate on John how a good kiss should go. This makes Richard insecure of himself, and Nelle tells him to find a theme song for himself. John loses the case to Larry, but he and Kimmie go out on a date.

The Christmas season is approaching, and while Ally is thrilled about it, Larry has nothing to celebrate. He confesses to her that he has a 7 year-old son who lives in Detroit with his mother, and ever since they split Larry finds Christmas sad and lonely. Meanwhile, Kimmie insists that John sings at the bar after he lies about his college band, and he doesn't do as bad as everyone thought he would. Elaine is lonely and performs at the bar to regain self esteem. Mark asks her out on a date. John and Ling handle a case about a news anchor who was fired for saying on TV that there's no Santa.

Elaine gets sued by a former office clerk because she called him "peanut" due his size. John thinks Larry was ridiculing him by making fun of his relationship with Kimmy and her mother. Nelle and Ling compete about who will have the most bids from the charity auction dinner date and Cindy (Mark's ex-girlfriend the transvestite) has plans for Richard for charity auction.

John and Nelle defend her father who was fired from his job as a teacher because he claims he's Santa Claus; Ally feels threatened when Larry's ex comes to town;Richard and Ling lip synch at the office Christmas party.

"The" Nicholas Engbloom comes to Cage & Fish looking for John to help him with a murder case. Melanie West suffers with Tourette's syndrome and accidentally ran over her boyfriend. She claims to have done it on purpose, only not to be humiliated as she has been her whole life. John convinces her to tell the truth and they win the case. While handling the West case, Nicholas finds himself involved in a divorce case. His wife wants to end their long time marriage because he won't retire and she feels like she can't compete with his work. After his wife almost dies, Nicholas abandons the practice, this time forever. Meanwhile, Richard teaches Mark how to use a "sex song" in order to please Elaine in bed, and John asks Melanie on a date.

Larry's ex-wife asks him for his permission to take their son to Canada, where she is moving. They argue over why can't one of them move closer to the other so their son can grow with his two parents around. Jamie asks Larry why can't they get back together and Larry says because she's not Ally. They kiss. Larry tells Ally, who overreacts about it until he explains her that Jamie is and will only be the mother of his son. They make up. Meanwhile, Ling's ex-fiancee comes to ask her if they still have a chance, but Ling doesn't want to destroy her girlfriend's happiness. Melanie is fired from her job for scaring the children and John takes it to court.

Melanie takes John to her tiny apartment (actually it's an old service elevator) and introduces him to Mr. Bo, a homeless man Melanie cares deeply for. Mr. Bo starts to stalk John around and he files a complaint against him. After Melanie convinces him to drop the charges, she reveals that Mr. Bo is in fact her father and John will have to wrestle him in order to go on seeing her. Meanwhile, Richard organizes a twist contest at the bar and while Elaine freaks with the possibility of losing to the babe lawyers, Nelle only enters the contest after Ling introduces her to a very hot twist instructor. And Ally takes a case of a woman who fired her secretary because she was slightly overweight and is shocked when she discovers that Cage & Fish only hire hot female lawyers.

Larry's son flies in from Detroit and goes to Cage & Fish looking for Ally. He wants to sue his parents for emotional damage. Ally and Sam bond, and Larry has to take him back to Detroit. He doesn't want to say goodbye to Ally, who suffers with his departure. Larry promises to return. Meanwhile, Nelle is representing her dance instructor/lover Sam Adams in court. He's suing his ex-partner for stealing his dance moves. Cindy McCauliff returns to the office looking for Richard. (S)He wants to marry a man, but after the court denies it Richard offers to perform the ceremony at the office.

Ally has hallucinations with Barry Manilow. Richard assigns Ling to work with Jackson Duper, the firm's newest lawyer. When they meet, Ling discovers that Jackson slept with her in the past under a fake name. They have to handle a double case of a man who wants his marriage annulled because his wife is a nymphomaniac and cheated on him 106 times and is suing the minister for having a torrid affair with her. Between the unisex bathroom, Elaine's vibra and Melanie's Tourette, Jackson is going crazy with his new job and questions his future in the firm. Meanwhile, John proposes to Melanie. But Melanie doesn't want to be institutionalized (even if that institution is marriage)...

Richard and John's relationship grows more tense than ever and so they attend couples therapy; Jackson's presence has a profound impact on Elaine; Jackson represent a woman being sued for firing all her male employees.

Jackson and Renee's one night stand turns into something more; Ally visits several therapists to get over her hallucinations of Larry, who eventually appears in the flesh; John represents a man who wants to annul his marriage after his wife decides she doesn't want to have kids, a case that carries over into John's relationship with Melanie.

To escape their ruined love lives, Richard and John go for a vacation to Los Angeles. It turns into a working vacation however when John not only must get Richard out of legal trouble but also helps a woman divorcing her wealthy husband who paid someone to seduce her. Meanwhile Richard helps a struggling actress leave her agent who is in fact using her to run an escort service.

Elaine cheated on Mark and now she's trying by all means to find a way for him to forgive her. She even takes advice from Richard! But in the end she has a serious talk with Mark and she tells him she cheated because he never fully trusted her. They break up. Meanwhile, Jackson is assigned to do the pre-nup for a rich, fat and bald man. Ally puts Larry to defend to soon-to-be wife's interests, which leads into a more personal dissension between Larry and Jackson. And Ling takes the case of a man who's being sued by his own son because a blood clot has left him perpetually happy which is ruining the family business.

Cassandra surprises John when she suddenly shows up at the office. She wants to continue the relationship they started in LA, but John doesn't want to go on seeing her, because they're 3.000 miles away and he's not completely over Melanie yet. Ally takes the case of a man who's being sued because he didn't reveal to his internet date that he was a dwarf. Larry is representing the woman suing, and the case ends up reflecting on their own relationship as Ally questions Larry if they would be together if she was 3 feet tall. Ling and Jackson take a case of a woman who's suing her old boyfriend for interrupting her wedding ceremony. Jackson reveals his true feelings towards Ling, who is confused and torn between him and Richard. Caught in the middle of this is Renee, who feels used by Jackson.

John loses his ability to channel Barry White while going up against Larry in a case involving a man who wants to clone his late wife; Nelle hooks Elaine into on-line romance; Ling's feelings for Jackson grow more intense.

Larry defends Sting when a man sues him for breaking up his marriage; a Streisand impersonator sues over his nose job; Richard flirts with Cindy Margolis to make Ling jealous.

Sydney Gale hires Cage & Fish to represent her in court. She's been sued for wrongful termination, and Richard and John take the case. An employee is suing Sydney because he doesn't want to 'serve' her anymore. In her firm, she only hires men who desire her, and thus make the company a lot like a beehive and Sydney their queen. John and Richard are driven crazy with lust, but they win the case. Meanwhile, Reverend Mark Newman is once again having problems concerning Lisa Knowles's performance at church. Now she's musically attacking Rev. Mark's new girlfriend, who's also a member of the choir. After Jackson's strategy fails, it's in Nelle's hand to fix the situation.

Ally becomes extremely jealous over Larry's easy friendship with his ex-wife; Richard tries to stop a magazine from publishing photos of his LA friend, Jane.

Malcolm Wyatt hires Ally to take his case. He's suing a girl for not going to the prom with him after she said yes in fall. The opposing lawyer is Larry Paul, and Ally is nervous about meeting him in court. But he never shows up, and his partner Coretta tells Ally he left for Detroit. Richard hires Jane Wilco as the office's new secretary, but after she gets the cold shoulder from some people, Richard wonders what ever happened to the friendly workplace he once built. Ally talks to Billy's ghost and decides to go to Malcolm's prom as his date and convinces him to sing solo and never stop believing in love.