In "Mr. Monk Goes to the Office," Adrian loses his standing in the office gang because he wouldn't put on someone else's bowling shoes even though it meant losing the game. So, it is highly unlikely that he would put on a Santa suit, mustache and beard that had been worn by many past Santa Clauses.
When Frank is being questioned, the scene inside the interrogation room alternates from being mirrored to being normal. Monk and Stottlemeyer alternate from being on Frank's right in normal scenes and to his left in the mirrored scenes. The visitation rules on the wall confirm the mirroring.
The poisoned detective lands on his back with his head turned to his left side, but when the camera changes, his head is turned to his right.
Disher: I used to have a rock band back in high school. The Randy Disher Project.
Stottlemeyer: That's a good name. How'd you come up with that?
Disher: Well, my name's Randy... Disher, and then... Project.
Stottlemeyer: Terry, hey! That's not straight. The left side is too low.
Terry: It's good enough.
Stottlemeyer: No, it's not. Adrian Monk is coming.
Terry: Ah, hell. Okay.
Monk: That's the Cadillac of first-aid kits.
Sister Heather: You have strong feelings about this.
Stottlemeyer: You're godda--yes.
Alice Westergren: How late do these things usually go?
Stottlemeyer: Last year, Karen and I left around 2:30 a.m. And Terry--Detective Chasen--was still standing on a table in his boxer shorts, singing "Help Me, Rhonda." In Spanish.
Detective Chasen: That's a lie. I don't speak Spanish. (Grins.)
Stottlemeyer: Ah. Yes, you do.
Stottlemeyer: (reading the Christmas card accompanying a wine bottle) "Captain Leland Stottlemeyer. Thank you for your business. Eastwood Auto Supply." (to Alice) You know what this is? It's a bribe. Someone is trying to influence public policy. And I think it might work.
Julie: (looking at a snow globe) Is it beautiful?
Monk: Is what beautiful?
Monk: You've never seen snow?
(Julie shakes her head)
Monk: Oh, it's very beautiful. No two flakes are the same. But somehow, it's still beautiful.
Julie: Who's that for?
Monk: Oh, this is from Trudy. It's for me.
Natalie: From Trudy?
Monk: Yeah. After she died, I found it. Every Christmas, I put it under the tree.
Julie: You've never opened it?
Monk: (to Natalie) It's going to be a great party. I'm not completely dreading it.
Monk: I don't go out much during the holidays. It's too depressing. Because I'm alone. I don't have to tell you. I mean, you're not married, right: You don't have anyone.
Alice: That's true.
Monk: It's tough. Especially for people our age.
Monk: It's a--it's an air purifier for your house.
Stottlemeyer: Are you saying my house smells?
Monk: Not your house. But houses--like yours--sometimes get a, um, odor that's, uh, sour. Very unpleasant stench. Not your house.
Stottlemeyer: Do you know, um, what eBay is?
Monk: Ah. Oh. It's a funny card.
Alice: Yes, it is.
Monk: You can tell because--exclamation points.
Stottlemeyer: What are you doing?
Disher: I'm picking my team. I'll take, uh, I'll take Monk.
Stottlemeyer: (grabbing Monk's suit jacket) No, I'll take Monk.
Stottlemeyer: Monk, I can't go near the place. The wife filed a complaint against me. Said I'd been harassing her.
Monk: Why would she say that?
Stottlemeyer: Probably because I'd been harassing her.
Monk: Who are all these people? These folks have forgotten the true meaning of Christmas.
Natalie: Yeah? Which is what?
Monk: Which is leaving me alone.
Natalie: Well, I love everything about it. The crowds, the shopping, the decorations...
Monk: The fact that it's horrible doesn't bother you?
Natalie: Oh, my gosh. I can't believe he's still here.
Monk: Who's here?
Natalie: Mr. Preston. I used to work here.
Monk: Wait a minute. How many jobs have you had?
Natalie: Mr. Preston liked me... a lot. A little too much.
Monk: I've never had that problem.
Monk: (as Santa) What do you want for Christmas?
Little Boy: A rock polishing kit.
Monk: You're Santa's favorite.
Natalie: (as Santa's helper, abouit Monk) We have some new rules here in Santa's workshop. Before anybody can sit on Santa's lap, you have to use these magic wipes.
Disher: Wait. Wait. there's a nun in there. She won't leave.
Stottlemeyer: A nun?
Disher: She's sort of nice. She has--a nunny quality.
Sister Heather: My father once taught me an important lesson. There's no revenge so complete as forgiveness.
Stottlemeyer: Your father.
Sister Heather: He's your father, too.
Stottlemeyer: How was I supposed to know that was the letter M? This guy's the best detective in the Free World. He didn't know it was an M. (pause) You couldn't use a spray can like everybody else?
Julie: A first-aid kit?
Monk: That is a hot gift this year. There's the Cadillac of first-aid kits. We're talking about one hundred feet of gauze, five kinds of ointment, and a tourniquet...
Monk: (looking at a goldfish he's received as a present) It's alive. It's a living thing. Is it going to die?
This was a bonus Christmas episode.
The guitar that Captain Stottlemeyer plays in his duet with Disher singing "Oh, Holy Night" belongs to the captain's wife, Karen. Disher notes that he has a Gibson guitar at home, a souvenir from his high school band, the Randy Disher Project, which is first mentioned in this special episode.
This special episode is listed as part of the season five sequence because the site is not set up to give it a number of its own.
Sister Heather: My father taught me an important lesson. There is no revenge so complete as forgiveness.
This quote is actually from Josh Billings, an American humorist who lived from 1818-1885.
Stottlemeyer: And Terry--Detective Chasen--was still standing on a table in his boxer shorts, singing "Help Me, Rhonda." In Spanish.
In "Help Me, Rhonda," a Beach Boys hit from 1965, songwriter Brian Wilson tells "Rhonda" that the girl he intended to marrry "let another guy come between us/And it shattered our plans." Detective Chasen, who reputedly sang the song at the previous year's Christmas party, is about to have his own plans irretrievably shattered.