Representing an artist who can't forget his dead wife conjures up ghosts of once-in-a-lifetime love for Ally and Billy; Cage worries about kissing Ally as their first date looms.
- Calista Flockhart as Ally McBeal
- Courtney Thorne-Smith as Georgia Thomas
- Greg Germann as Richard Fish
- Lisa Nicole Carson as Renée Raddick
- Jane Krakowski as Elaine Vassal
- with Peter MacNicol as John Cage
- and Gil Bellows as Billy Thomas
- Steven Flynn as Sam Little
- Brigid Brannagh as 'Paula
- Phil Leeds as Judge Dennis 'Happy' Boyle
- Bruce Nozick as Attorney
- Vonda Shepard as Herself
- Richard Kiley as Seymore Little
The day before her first date with Cage, Ally realizes she doesn't want to go out with him and manages to avoid him before the morning meeting. Fish assigns Ally to represent Seymore Little, a famous elderly artist whose son/guardian won't let Seymore marry his twenty-something fiancee. After the meeting, Cage tells Fish that he is worried about whether or not to kiss Ally on their date. Fish tells him women like men to be aggressive.
Ally meets with Seymore, who wants a lawyer in pants, not skirts. Fish assigns Billy to work with Ally. They talk to Seymore and his fiancee, Paula, who fail to convince the lawyers that they are really in love. Ally talks to Seymore's son, Sam, who insists his father cannot be in love with Paula because he still talks to his long-dead wife, the love of his life. Seymore admits this, but says he loves Paula too. Ally and Billy do not believe him.
Back at the office, Cage tells Fish he fears dates because he is a poor kisser (too much saliva). Fish tells him to ask Billy's advice on how Ally likes to be kissed.
In court, Sam's attorney says Seymore once bought a very expensive boat at his dead wife's "request," which is proof of Seymore's incompetence. In private, Ally asks Paula why she really wants to marry Seymore. Paula, like Seymore, refuses to talk.
Cage asks Billy's advice about kissing Ally, but Billy is very uncomfortable with the subject.
After the first hearing, Sam offers Paula all of his father's money not to marry Seymore, but Paula refuses. It proves she is not after money, but confounds everyone about her true motives. Ally and Billy spend a late night puzzling over the case, but only get caught up in tensions about their own "once-in-a-lifetime" love.
The next morning, Ally admits to Renee that she's "backsliding" a bit in her feelings for Billy, but vows not to relapse totally. Tensions remain between Ally and Billy, however, as he counsels her on putting Seymore on the witness stand. In court, Ally's questioning goes well at first. But when Seymore is asked about his wife, it is obvious he is still grieving. Soon, he begins talking on the stand to the dead woman, proving Sam was right all along.
After the hearing, Ally confronts Paula, who finally admits she only wants to marry Seymore so she can become his guardian and allow him to open a gallery to sell paintings of his dead wife, which Sam, Seymore's current guardian, won't let him do.
Cage rehearses for his date with Ally by listening to Barry White music. Elaine gives Cage kissing tips, showing him how to suck back his extra saliva during the kiss.
Ally and Billy talk to Sam, who shows them Seymore's paintings of his late wife. They are good, but not up to the standards of his younger work. Sam fears they will ruin Seymore's artistic reputation if sold to the public. Back at the office, Cage intercepts Ally and hustles her out for their date. Ally begins her dumping strategy by launching into a non-stop, boring monologue about clothes and make-up. She keeps it up during dinner, dancing and the walk to her apartment. Finally, at her door, Cage lunges at Ally with a kiss so deep it literally knocks her to the ground. She escapes into her apartment as fast as she can.
In the morning, Cage frets that he was "untoward." Ally visits Seymore, who admits that all he wants is to open his gallery. Back at the office, Ally (literally) runs into Cage, and is forced to admit she has no interest in dating him. He senses that it is because she is still in love with someone else...who is probably still in love with her, too.
Wrapping up her case in court, Ally argues that everyone would be lucky to experience a love that would not die. The judge decrees that Seymore be allowed to open his gallery. That night, Georgia and a still-distracted Billy go dancing, Seymore gazes at the paintings of his late wife, Cage adjusts to being dumped, and Ally walks home alone.