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.

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.

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)...

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.

It's a new year at the firm, which means changes - big changes! Still getting over Larry and renewing her faith in love, Ally decides to start fresh and let nothing get in her way. That is until she barrels into a woman on the street with her Razor Scooter. She runs into Jenny Shaw (Julianne Nicholson) and instantly bonds with this new broken-hearted stranger. In the time it takes to walk the rest of the way to the office, Ally finds out that Jenny's best friend is her ex-boyfriend, former co-worker and that Jenny is a lawyer without a firm and with a class action lawsuit housing 72,000 plaintiffs!

Ally brings Jenny into the firm and announces that she's hiring her. Of course Richard is surprised because only he has hiring authority. He then lets Ally know that he already hired the latest addition to the firm.

Jenny insists that Ally should go out with Glenn, and Ally insists she doesn't have a crush on him. The three are assigned to chair the telemarketing case. They have a very hard time with the main plaintiff, Claire Otoms, a purple-haired, flashy-looking lady who lives in a 'colonial house'. Raymond, knowing that if the judge listens to her he'll rule in his favor, takes the deposition to the court. Claire keeps drifting from the questions, for Ally's desperation. But what appeared to have gone so bad turned out good. Coretta convinces John that he must look good to cause a good impression, and John ends up dressing a fake muscle suit to try to get rid of his weird-women magnetism. Ling and Nelle 'compliment' twin babies on the street. The mother of the babies - the Massachusetts governor - is so flattered by the compliments that she offers Ling a judge position. Overwhelmed, Ling makes a purple robe and starts to give more-than-quick sentences.

Ally has a dream about Raymond and Glenn. She thinks it's a sign they'll lose the phone company case, and Glenn sees it as a secret attraction of Ally for him. After Raymond makes a 125,000 dollars offer for the phone company case, Ally decides to make an infomercial using Ling's TV show crew and Claire Otoms as the announcer. They threat to run the infomercial nationwide on primetime, and the threat of losing hundreds of millions of dollars scares Raymond's client. Cage & Fish settle for 15 million dollars, the biggest settlement ever, which makes Richard cry of happiness. Meanwhile, Ally is still divided with her feelings for Glenn and if she should date him or not. Glenn says he's not interested in her, and Raymond asks Glenn if he should date Ally. To make things even better, John decides to confess his feelings for Ally and is very disappointed when she says they will never be more than just very good friends.

Ally and Glenn continue their flirtation, which leads to their conscious avoidance of each other, which does not go unnoticed by the others at Cage and Fish. She insists he’s too much of a “boy” for her, but continues to be attracted to him. He’s drawn to her because she’s a little older. Both use Jenny’s feelings as an excuse to not date as well. John takes off for parts unknown, which worries the ladies of the firm, especially Nelle. Richard takes it in stride, and takes over John’s abandoned hole off of the unisex. Raymond is sued by a former coworker for sexual harassment, and asks Jenny to represent him...

Jenny's mother comes to hire the firm to take her wrongful termination case. She's being fired from her job for dating a 20 year-old. Jenny wants Ally to purposely lose the case but Ally can't do that. The case ends up serving as a mirror to Ally and Glenn's relationship. Ally's closing makes Jenny change her mind and she accepts her soon-to-be step-father. Glenn tries to reach Ally, but Ally, as always, is afraid she's going to end up broken hearted. Meanwhile, Ling looks for more exciting cases for her show and brings an entire orchestra to her court. Richard obsesses with Ms. Shaw's waddle, but Francis shows him he's way out of her league.

John makes a surprise return and is shocked after hearing from Raymond that Richard threw a party in his "hole". After confronting Richard, John gives the office a speech, in which he reveals the reason why and where he left to. Raymond gets Glenn and Ally to double date with him and Jenny. It's Jenny's birthday, and everyone forgets it. Glenn is the only one who didn't get her a present, so he sings a very romantic Elvis song at the bar for her. He asks her back, and she accepts. Ally wonders if she should hook up with John, but the ghost of Larry is still present in her thoughts. Meanwhile, Ling poses nude to boost her TV character; Corretta and Richard find themselves involved in a police investigation on a woman who used to marry rich old men for the money

Jenny's mom's wedding is approaching, and Ally is shocked when Tim gives her a certain look that suggests a move. She talks to Jenny, and they decide to test him. Ally makes a move on him, and he offers her to have an affair. Surprisingly, Jenny's mom is ok with that, which only confuses Ally more. She's been hallucinating with a 7-year-old boy who keeps saying she's killing him. The boy is a version of Ally from when she believed in love (a conclusion made by Richard), before Billy died and Larry left. Meanwhile, John and Coretta help Kimmie Bishop, who's back suing a matchmaker for saying she's "unmatchable".

Ally impulsively buys a house, to which Dr. Milter concludes is a way of her to take care of herself, since Ally sees herself as a 'work in progress'. Richard gets the others to help paint the house as a surprise for Ally, who hires the handyman Victor to fix the house for her. Meanwhile, Ally handles a case of a man who spent too much money buying gifts for his wife until they went bankrupt. And Jenny has some back problems, to which Coretta recommends a chiropractor who has a special chair. Glenn gets extremely jealous that a chair is giving Jenny more pleasure than him, while Nelle tests the chair.