Ally defends a man who broke into his old house to jump out of his old bedroom window. Harvey Hall believes he can fly using wings he made himself. The house owner allows him to jump from the roof, and Harvey accomplishes his life long dream of flying, at the cost of his own life. Meanwhile, Harriet Pumple tries to find a match for Elaine, Coretta, Richard and John. She matches Elaine with Victor, who would have dumped her if it wasn't for Ally asking him not to. But Harriet can't find a match for John, so the entire office sings "we have to get you a woman" for him. John is profoundly insulted.

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...

Ally and Victor return from their Bermuda trip. Ally feels their relationship is in crisis because they weren't able to connect without Maddie around. Victor is being sued by his former girlfriend for breach of contract. Ally discovers that Victor is a painter and never told her. She's angry, but not as angry as when she sees his painting of her with cellulite. Nelle and Wilson team up against a woman who was blackmailing their client in order not to come public with a tape of their lovemaking. Richard obsesses over Liza and has Claire do the talking for him through a hearing device, afraid she's going to turn him down - and even more afraid she'll say yes to him.

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.

The first case Georgia brings to Renee's new firm pits them against Cage and Fish. Georgia defends Newman's, an upscale department store against Steve Mallory, who worked as the store's Santa for seventeen years. Cage represents Mallory, who claims that he was wrongfully fired because Newman wants to hire a younger, thinner Santa. Meanwhile, Ally is haunted by visions of herself as a little girl. Ally manages to bring Georgia and Billy together to talk, and Billy sees that he wants Georgia back. But Georgia is not as eager to work things out yet.

Things go awry when Ally introduces Brian to her parents, resulting in conjuring up old pains and hurt feelings. Meanwhile, Nelle regrets her decision to leave Cage and Fish, and takes steps to rectify it. Also, it's John's birthday - emotional, entertaining, with lots of musical numbers.

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.

Ally gets arrested for fighting with Hannah, a distraught young woman who is struggling with her best friend stealing her boyfriend. Ally offers to represent her later in court, only to learn that Hannah has a habit of firing her lawyers. George Madison meanwhile has come back to the firm to get some legal counsel in starting up his own magazine. He hopes Ally will help him, much to Elaine's chagrin. Elaine, desperate to win George over, sits Ally down for a heart to heart talk and asks Ally not to take George away from her. Cage and Nelle have an awkward moment when she insults his pet frog, which is about to compete in a jumping, contest, which Cage is set on winning. Hannah's case goes to the jury after a brief defense by Oren Koolie, who puts in an impassioned appearance.

Upon discovering her favorite high school teacher is terminally ill, Ally seeks a court order to allow the women to spend her remaining days in a drug-induced coma, happily dreaming of her imaginary lover. Cage must gather his courage to confront Nelle after Fish tells him she thinks Cage has not had sex with her because he's gay.

The firm defends a woman accused of murdering her eighty-nine-year-old husband by suffocating him with... her breasts. Meanwhile, Ally struggles with turning thirty. She goes to church to find God, but instead finds an angry Reverend Newman who has a pet peeve about women who only need God between relationships. Ally's next stop at a plastic surgeon has even more devastating results.

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.

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.

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.

10 year-old Maddie Harrington shows up on Ally's door saying she's her daughter. She's the result of a mixup on the egg bank Ally deposited her eggs ten years ago. Since Maddie's father died six months ago, she's been living with her aunt, who sings TV themes on nightclubs for a living. After a lot of talking, Maddie decides to stay in Boston with Ally on a trial basis until they resolve where she will stay. Meanwhile, Richard takes the case of a man who killed his wife after kicking her in the head when he mistook her for a soccer ball. John doesn't think he'll be able to win the case because he can't litigate, but Richard surprises him when he wins.

Maddie keeps testing Ally for her patience and love, something that doesn't go through Ally's mind until Victor points it out. Ally, on the other hand, is being way too protective on Maddie, confronting her school principal, teacher and classmates. She decides to hire a nanny, but can't find one that is fits her standards (liking Moulin Rouge, for example), so she ends up hiring Victor, who has developed a very good bond with Maddie. As if she didn't have enough going on in her life, Ally is offered partnership on the firm now that John is gone. After a lot of consideration, Richard decided to ask her and change the firm's name from Cage & Fish to Fish & McBeal, which upsets Nelle, who thinks she should be the next partner, not Ally. After going through the firm's books, Ally discovers that they're losing money and have to fire someone to avoid problems. Since neither Richard nor John had the guts to fire anyone, Ally decides to do so. Meanwhile, Coretta and Raymond face each other in

Ally decided that in order for the firm to get out of the financial crisis it's going through, someone will have to be let go. She chooses Jenny, who between all the lawyers of the firm had the least number of clients and experience. Glenn takes Jenny's dismissal offensively and decides to quit, taking all his clients with him. Ally accepts his resignation, but Victor convinces her to hire him back since the firm can't afford to lose any clients. Glenn and Jenny decide to start a new firm together and leave Cage, Fish & McBeal once and for all. Now the other lawyers will have to do extra work to make up for the loss. Among the changes Ally is making on the firm, she wants Nelle to be nicer and asks her to perform at the bar, something she has never done before. Afraid of embarrassing herself, Nelle goes to Ling for help. They decide to have backing vocals, a plan that backfires when the singer who was going to dub Nelle suddenly loses her voice and Elaine has Claire Otoms to replace he

Ally decides to take the DNA test after having recurring dreams where Maddie's real parents show up claiming her. Maddie doesn't take that well and escapes to NY to see her aunt Bonnie. Maddie thinks the test is just Ally's way of having an excuse not to love her, but Ally only wants a proof that Maddie is her daughter so no one can take her away from her. The test comes out positive, and they both cry. Meanwhile, a demented woman shows up at Ally's door looking for Vincent, the love of her life who owned the house before Ally bought it. She thinks Victor is Vincent, and he plays along. She has a stroke and dies, and Victor suffers from it even though he only met her for less than a day. Ally also offers Raymond a job at the firm, which he takes. And Claire decides to help Richard reunite with his high school crush, but she had a sex change operation and is now a man, something that shocks Richard deeply.

Ally has a chance encounter with Glenn, the well-endowed artists' model, at a local Starbucks, and makes it very clear that she is irritated with him. On the legal side, John Cage takes on a wrongful death case that Fish is convinced will reap big bucks for the firm. Two adult siblings are suing an airline after their father is killed in a plane crash.

Ally and Renee are bridesmaids at a friend's wedding. They both bristle at the absurdity of the rituals performed, and swear to never do it. Richard asks Ally to flirt with a wealthy new client. To Ally's chagrin, Cage offers no protest on her behalf, admitting he's undergoing smile therapy which has renewed his appreciation for behavioral reinforcement. Ally and Georgia try a case about overturning a prison warden's decision to refuse marriage for a life-term inmate.

The whole firm is angry at Richard for accepting another ridiculous lawsuit that Ling has come up with, but as usual, Richard has no problem telling it as he sees it. Renee inadvertently sets Ally up on a blind date from hell, and this time during the date, Ally gets herself stuck in another tight situation. John is continuously fraught over his relationship with Nelle, and things don't go well when he asks for advice or gets advice when he doesn't even ask for it.

Ally's heart is broken and not by Billy or Greg. It's just one big stress fracture. She's come to the realization that there isn't anyone out there for her. She has her image of the perfect man, but is beginning to believe that he does not exist. Surprisingly, a pep talk from Fish leads Ally to become more proactive about her love life. Working on the, "you have to kiss a lot of frogs before finding Prince Charming theory", Ally decides to go on a dating frenzy. She also decides to go for a total hair and fashion makeover. Nelle is starting to become annoyed with John Cage because he seems to be the only one in the firm who understands Ally's imaginary love life. Nelle is worried that John and Ally feed off each other and now that she and John are a couple, she would really prefer her man to face life head on.

Risa, the bride whose wedding Ally destroyed, decides to sue Ally for intentional infliction of emotional distress; Georgia expresses outrage when Billy hires a sexy twenty-year-old as his new assistant; Ling tells Fish that she has been faking in bed.