Ally is called to the office where she is introduced to John Cage, who is being charged for having sexual relations with a hooker. Ally is assigned to be the litigator on the case. When they come out of the office Elaine says the judge sitting on John's case will be Happy Boyle. Richard gets excited and calls for Billie, who seems to know judge Boyle.
In court everything is easily settled after judge Boyle approves Ally's teeth.
At dinner with Richard, Whipper and Ronald Cheanie, a rich potential client, Ally finds out she's on a double date as the escort of Ronald Cheanie, after Richard confessed that Whipper is there as his girlfriend.
But when Ally goes to the bathroom she sees Whipper kiss Cheanie.
Ally doesn't know wether she should tell Richard or not. First, she decides to ask Elaine how close Richard and Whipper really are. That's how Ally finds out Billy had a stripper at his bachelor party and she confronts him about it. Billy ends up admitting he never cheated on her like he cheated on Georgia with the stripper. Suddenly Richard and Ronald Cheanie come in. Cheanie asks Ally out to talk about the company and she's obliged to say yes.
During the date Ally tells Cheanie what she saw the previous evening. After he explains it and they talk Ally finds out she kinda likes him.
The next morning everyone celebrates landing Ronald Cheanie as a client, but Ally feels guilty and she tells Richard what happened between Cheanie and Whipper. Richard doesn't react very well.
Meanwhile John decides that he needs to give a speech because he feels like he lost the confidence of the office.
Then Ally talks to Billy about what she told Richard. He asks her if he should confess to Georgia about the stripper and Ally tells him he shouldn't, because it could only hurt her.
Billy also tells Ally that Whipper is a judge, so she goes to the courthouse to talk to her. Whipper is mad Ally told Richard about the kiss, but she's also worried about Richard's feelings. She walks out of the office telling she should talk to him.
Back at the office Whipper hasn't showed up yet to talk to Richard and when Ally walks into her office Ronald Cheanie is waiting for her. He doesn't understand why Richard refused him as a client and what's happening between him and Ally. She asks him to leave, but after he walked out she runs after him. She runs into Georgia on the way though, who asks her to have lunch some time. Suddenly John walks in and asks everyone's attention. He apologizes for his indescretions with the hooker and gives a speech that gives Billy the courage to talk to Georgia. Ally stops him before he gets the chance to tell her anything and she tells a story to make sure Georgia doesn't find out the truth so she doesn't get hurt.
Later, she's having a drink with Georgia as she promised and they have a good talk about men and sex.
When Ally is back in her office, John comes in and asks her to fill in a questionnaire about his speech. After he leaves Elaine walks in to ask Ally about Richard's whereabouts, because Whipper is looking for him. Ally takes Whipper to the bathroom where he's hiding and Whipper explains what happened and tries to win Richard back. Richard walks out upset, but when Ally sees that they truly do love each other she decides that she needs to talk to Richard herself. She tells him to give her another chance and he goes to see her again in the bathroom.
Afterwards Cheanie comes in and Ally tells him he can try to talk to her again in a week and after he leaves John comes in and asks her why she only gave him a two on the questionnaire. She explains she was offended by what he said and he explains what drove him to go to a hooker.
In the bathroom Whipper uses her wattle to seduce Richard into staying in a relationship.
Meanwhile Ally admits to Billy she wants to see Richard and Whipper together to keep her believe in love.