Mimi walks into the office, wearing a Christmas Tree outfit. Drew says Tommy Newman is late for their meeting, but Mimi laughs it off as Drew and Tommy aren't very high up in the corporate ladder. Larry comes in and gives him his vacation request. Mr. Wick comes in and asks Mimi to take care of the holiday window display. Larry asks if he can help decorate a window, but when he wants to expose himself, Mimi says he can't help. Tommy comes in and Drew gives him some advice, but it turns out Tommy is now Drew's boss, which is a bit awkward.
At Drew's everyone is gathered in the living room. Drew comes down with new pants on, and it turns out his pants are so new they actually make noise when he walks.
At the college, Drew comes into the room, and meets a young, attractive woman. Drew ends up getting paired with the only other "old" person in the room, and Drew's not too pleased about it.
At Winfred Louder, Mimi and several other co-workers are gathered around, all ready to get into a Christmas-themed scene, but Mimi receives word from Mr. Wick that they need to get back to work.
At Drew's he's studying with the woman he met at the college. They decide to take a break for a beer. She asks Drew about his personal life, and she seems to be a little impressed. She decides to leave as it's getting late. They walk outside, and end up singing, dancing, holding hands, and then kissing.
Kate, Lewis, and Oswald come over the next morning, and realize Drew had someone over last night. They're a bit shocked when they hear who Drew had over.
At the college, someone takes Celia's chair, which Drew tried to save. Celia comes in a bit late for the class, so Drew walks over and asks her if she'll go out with him. She turns him down, and doesn't want to study with him either.
At Winfred Louder, Mr. Wick tells Mimi that several Winfred Louder Gold Card Club Members want to boycott the store for Mimi's display, which has her posing as Mary. Mimi tries to settle everybody down, and it seems to work. Drew comes in and tries to ask Larry about dating older women.
Drew catches up to Celia, who is playing Bingo. He wants an explanation for why she won't go out with her. Celia says this is just a school-boy crush and she doesn't want anyone talking. Drew goes up and takes over the microphone, making it well-known to everyone about their relationship.
The show ends with Oswald and Lewis playing Bingo. Lewis is using stamping several dozen cards, but Oswald wins, using just one card.
I enjoyed this episode quite a bit. The plot was a bit odd, but very funny.