Ally runs into Kimmie Bishop, an old friend of hers from college. Ally makes fun of her in front of her fellow puritan friends, and Kimmie is so outraged she decides to sue Ally for defamation. Instead of having someone from the office to defend her, Ally hires therapist/lawyer Larry Paul. When Renee tells her he's married, Ally freaks. At the bar, while trying to decide if she would date a father or a son, she sees Larry with Nelle. Turns out he's divorced, and so Larry dumps Nelle to go out with Ally. Meanwhile, Mark is having a hard time at the office because nobody approves his relationship with Cindy, so he breaks up with her.

Kimmie comes to Cage & Fish looking to hire Ally. She's suing her old firm for wrongful termination. They fired her for being too puritan, and the opposite lawyer is Larry. Now Ally and Larry have to face each other in court. Meanwhile, Ally is nervous about her first kiss with Larry and seeks for advice with Ling, who demonstrate on John how a good kiss should go. This makes Richard insecure of himself, and Nelle tells him to find a theme song for himself. John loses the case to Larry, but he and Kimmie go out on a date.

The Christmas season is approaching, and while Ally is thrilled about it, Larry has nothing to celebrate. He confesses to her that he has a 7 year-old son who lives in Detroit with his mother, and ever since they split Larry finds Christmas sad and lonely. Meanwhile, Kimmie insists that John sings at the bar after he lies about his college band, and he doesn't do as bad as everyone thought he would. Elaine is lonely and performs at the bar to regain self esteem. Mark asks her out on a date. John and Ling handle a case about a news anchor who was fired for saying on TV that there's no Santa.

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.

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".