After discovering that Lynn has applied for yet another grad school program, Joan and Toni determine that they must end their financial support and force her to get a job and go out into the real world. However, Joan has difficulty completely cutting Lynn off, leading Toni to conclude that Joan is an ""enabler."" Meanwhile, William encourages Yvonne to hang out with the girls so that he can have time with his guy friends; and Maya suffers from the side effects of hormone therapy.

Toni cheats on Greg with Clay and winds up contracting chlamydia. Joan frets about the fact that Sean has yet to tell her that he loves her, especially after he reveals that he has been offered a six-month job in New York. She seeks her friends' advice on how to coax a love declaration from him. Meanwhile, Maya feels threatened by the temp who filled in as Joan's assistant during her absence.

Maya befriends Stan, a man she meets at the office and helps get a job. He encourages her aspirations to return to school. Maya initially tries to fix up Joan and Stan, but soon grows jealous. Toni joins a protest against a rapper in the hopes of winning God's approval. William searches desperately for a best man.

Ellis goes all out to give Joan a magical Valentine's Day, but the couple's future is put in jeopardy when he learns that his ex-girlfriend is about to have their child. Toni finds her Valentine's Day card from Todd offensive, and fears that he is only dating her because she is black. William cannot bring himself to tell Monica that he quit the law firm.