Natalie: Trudy's desk?
Adrian Monk: For five years. She loved this job. I did that. I was leaning in to kiss her, spilled some coffee.
Natalie: I'll bet it was the last time you spilled anything in your life.
Adrian Monk: I spilled something seven years later, January 12, 1999.
Natalie: January 12? You mean during the earthquake?
Adrian Monk: Earthquakes count. I don't make the rules.

Lieutenant Disher: If we were both drowning, who would you save?
Captain Stottlemeyer: I don't know. Both of you.
Lieutenant Disher: No, if you could only save one of us.
Captain Stottlemeyer: Well, I'd probably save Monk because he can't swim and I happen to know you're an excellent swimmer.
Lieutenant Disher: Suppose I was holding an anchor.
Captain Stottlemeyer: You're holding an anchor?
Lieutenant Disher: Uh-huh. Who would you save then?
Captain Stottlemeyer: Well, why don't you let go of the anchor?
Lieutenant Disher: It's a family heirloom.
Captain Stottlemeyer: I'm leaving.

Adrian Monk: [at Trudy's grave] She's not you. It's not you. [to a woman at another grave] Hey, how you doing?
Woman: Hi.
Adrian Monk: My wife is buried back there. She's still dead. She's right where I left her.
Woman: Okay.
Adrian Monk: I am so relieved. I mean, I love her with all my heart but... Who is this?
Woman: This is my husband.
Adrian Monk: Oh, I'm sure he's dead too. And he'll stay dead. Don't worry about that. This is an excellent cemetery. They know what they're doing. Yeah, everybody here, probably dead. Nice talking to you.