Ally McBeal Season 5

Ally finds herself the mentor for young lawyer Jenny, whom she runs into on the street and immediately hires as an associate at Cage and Fish. Neurotic Jenny, fresh from being fired by her old firm, and from heartbreak over a failed relationship, comes face to face with both her firm when she opposes its lawyers in court, and her old boyfriend, when it turns out that he is the other new associate at Cage and Fish. Meanwhile, John misunderstands Ally when he overhears her say she loves him, and sets out to win her heart. He seeks advice from Richard, waxes poetic to Ally, and after those and other attempts backfire, ends the hour with the realization that she does not love him in the way that he had hoped.

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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.

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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.

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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.

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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.

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