Natalie: Mr. Monk, let's come over here.
Adrian Monk: Strange. Fingerprints, but no palm prints. There were two of them. The housekeeper surprised them. There was a struggle. She pushes this alarm. She hits her head and falls here. This painting is it valuable?
Sherry Judd: Not really, except to me. It's my great grandmother. Why would someone do something like that?
Adrian Monk: Did you have spray paint in the house?
Sherry Judd: No.
Natalie: So they must have brought it with them.
Adrian Monk: Thank you. This is the housekeeper's blood. So they defaced the painting after they killed her, after the alarm sounded. They risked everything? They risked life in prison to deface your great grandmother? I think that's why they were here. To do this.
Natalie: To draw glasses and a mustache?
Adrian Monk: And a little goatee.

[flashback:]
Young Sherry: How much do we have?
Young Monk: [shakes tin] $18.25.
Sherry Judd: How do you do that?
Young Monk: I don't know. [chuckles] It's kind of funny, raising money for a dance that neither of us is going to. Uh, Leo, here's the thing, you gotta pay for that.
Leo: [wolfs down cupcake] Pay for what? Where's your evidence, Columbo?
Young Sherry: Leo, I'm telling principal Thicket. I'm not kidding.
Leo: You don't wanna do that, Sherry. You'll be sorry. I mean it.
Young Monk: Are you gonna pay us or not? [Leo squirts chocolate sauce on Monk's shirt]
Young Sherry: Leo, I'm telling. I'm serious! Here, it's okay. It's only chocolate. Here. [hands Monk a serviette]
Young Monk: Thanks.
Young Sherry: You should carry these with you.

Captain Stottlemeyer: It's just that your friend, Sherry Judd, just got a homeowner's policy worth a million dollars two weeks ago. That's pretty convenient, isn't it?
Adrian Monk: Well, that's ridiculous. You think she did it herself for the insurance?
Captain Stottlemeyer: No, no, she was in San Diego like she said. But she could've hired somebody.
Adrian Monk: No.
Captain Stottlemeyer: No?
Adrian Monk: She doesn't need the money. I got a look at that alimony check. She's getting 20 grand a month.
Captain Stottlemeyer: That's a lot of dough.
Adrian Monk: Thank you.
Captain Stottlemeyer: But Monk you and I have put enough rich people in jail to know that a lot of dough is never enough. They always want more.
Adrian Monk: Not Sherry. You don't know her. [off Stottlemeyer's look] What?
Captain Stottlemeyer: It's just that I haven't heard you talk about a woman like this for a long time.

[flashback:]
Young Sherry: How did you get all that chocolate out?
Young Monk: My mom makes me keep a backup shirt in my locker.

Natalie: I'm so sorry, Mr. Monk.
Adrian Monk: No, I'm happy for her. They seem like a great couple.
Natalie: Well, they're not a couple yet.
Adrian Monk: They will be. She's gonna go out with him.
Natalie: How do you know?
Adrian Monk: Well, I notice little things, like the way she said, "Yes, I will go out with you." She wrote her phone number on his hand and didn't let go of his hand for 27 seconds.

Adrian Monk: Natalie. Look at his gloves.
Natalie: Yeah, so?
Adrian Monk: No fingers. Do you remember the handprint on Sherry's wall?
Natalie: They were bikers?
Adrian Monk: They were bikers.

[flashback:]
Janitor: Kid, you all right?
Young Sherry: Adrian, are you okay?
Jimmy Wagner: He'll be scarred for life. Psychologically.
Janitor: Nah, he'll get over it. [Monk whispers in Sherry's ear] What did he say?
Young Sherry: He said he solved the case. He knows how Leo did it.