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.

Stan gives Maya an expensive watch for Christmas. Joan tells her to give it back to him, but she refuses. When Darnell sees the watch, Maya claims it is a gift from Joan, leaving him infuriated. Meanwhile, Vosco finally packs up and leaves for good after Lynn criticizes his Christmas present to her--a dog. William is excited about playing Santa for the office Christmas party, but experiences unexpected problems after getting a stain on the suit.

Yvonne accuses William of trying to control her after he surprises her by buying a house for the two of them. Joan objects to the firm's policy regarding Martin Luther King Day, as they insist on remaining open for the day. She goes out of her way to try to change Swedelson's mind about the topic. Maya continues to spend time with Stan, and William warns her about what he sees as Stan's true intentions.

After an uncomfortable kiss, Maya realizes that she was wrong to get involved with Stan, and wants to stop seeing him. Stan, however, reveals that he has fallen head over heels, and refuses to give up on her. He seeks revenge by forming a friendship with Darnell and threatening to tell him about the affair. Meanwhile, William recuperates at Joan's house after being dumped by Yvonne.

Joan is the subject of office gossip and jokes after she begins dating a younger man who works in the mail room. She is embarrassed by the attention, and winds up hurting Chris's feelings. William is upset when Chris usurps his spot as pitcher on the company softball team. Maya fears that the persistent Stan will expose their involvement to Darnell.