Natalie: For the record, my crush on the Frisco Fly is officially over.
Adrian Monk: He's not the Frisco Fly. He can't be. He can't be.
Natalie: [to merchandise vendor] No. No, thank you.
Adrian Monk: No.
Natalie: You know, Mr. Monk, you and Harold have a lot in common. I think that you could actually be friends.
Adrian Monk: I don't think so. The fact that I despise him would always come between us.

Dr. Kroger: I understand how upset you are, but the fact is that when I heard that it was Harold up on the roof, the Frisco Fly, I was as surprised as anyone. But whatever Harold did, whatever he accomplished, he did it on his own. I'd like to take credit for it, but it wasn't me.
Adrian Monk: So no matter how bad it got, no matter how low I sank, I could always say, "At least I'm not Harold Krenshaw." He was my northern star. He was the only thing in the world I could really, count on.
Dr. Kroger: You know, you're unbuttoned. Adrian, it's been a while since we talked about medication, but there are some new anti-depressants on the market.
Adrian Monk: It doesn't matter. I give up.
Dr. Kroger: Did you just say, "I give up"?

Natalie: Oh, they're never gonna catch him.
Adrian Monk: Who?
Natalie: The Frisco Fly. This is him on the Golden Gate bridge. This is him, three weeks ago, climbing Coit Tower.
The police always get there too late. He's like a real-life superhero. I wonder if he's single. I wonder if he needs an assistant.

Adrian Monk: He's late.
Natalie: He's always running late, Mr. Monk. Just relax.
Adrian Monk: If I could relax, I wouldn't be here, would I? It's Harold Krenshaw. He's in there right now. He knows I'm waiting. He knows it.

Adrian Monk: 11:02, Harold.
Harold Krenshaw: Sorry. I guess we lost track of the time.
Adrian Monk: I heard you crying.
Harold Krenshaw: I was not crying.
Adrian Monk: I heard you, Harold, through the wall.
Harold Krenshaw: We were laughing, you idiot. We were laughing. I told him a joke, and we both just started laughing.
Adrian Monk: He doesn't laugh.
Harold Krenshaw: Yes, he does. He doesn't laugh with you.

Adrian Monk: Go to hell, Harold.
Harold Krenshaw: You go to hell!
Adrian Monk: The only reason I would even consider going to hell would be to visit you.
Harold Krenshaw: You are really a sad, sad man. I don't know why Dr. Kroger even bothers.
Adrian Monk: [mimics a baby crying]
Harold Krenshaw: I wasn't crying. I wasn't crying. Natalie.
Natalie: Good-bye, Harold.
Harold Krenshaw: Bye.

Natalie: So how was your session? Mr. Monk?
Adrian Monk: Ah, Natalie! I just got it!
Natalie: Got what?
Adrian Monk: What I should have said to Harold! Oh, my God. A zinger! It's what they call a "comeback."
Natalie: Mr. Monk, I don't think it really matters.
Adrian Monk: No, no. Just listen, listen to this. Listen to this. I said Dr. Kroger doesn't laugh. He said, "He doesn't laugh with you." What I should have said is, "Maybe he's laughing at you, Harold." At you. Get it? At you. Get it? At you.
Natalie: Yeah, I got it.
Adrian Monk: It would have destroyed him! He'd be boxed in. He'd be boxed in. There's no possible response. At you. Let's call him.
Natalie: Call him?
Adrian Monk: Yeah. No! No, you're right. You're right, you're right. We'll go to his house. We'll do it in person. But we have to hurry before he forgets what he said!
Natalie: No, Mr. Monk. I don't think that's a good idea.
Adrian Monk: Please, Natalie. I have so little.
Natalie: No, forget it. I am not driving downtown so you can zing Harold Krenshaw. Why don't you just mail it to him?
Adrian Monk: It's not the same.

Captain Stottlemeyer: Now, this doesn't track, does it? The guy hits a deer, runs off the road, crashes into a rock, dead on impact, a few hours go by, maybe a day. Somebody comes along, a stranger. He files the VIN number off the engine, which would have taken a few hours, then torches the car and the body. Why?
Adrian Monk: Why, indeed. Is that poison ivy?
Lieutenant Disher: No.
Adrian Monk: Oh, thank God.
Lieutenant Disher: It's poison oak.

Harold Krenshaw: Look at me. I'm a hero sandwich!
Journalist: You were telling us about the accident.
Harold Krenshaw: The last thing I remember, I was almost at the top, which we call "the summit," and I lost my footing. I must've slipped.
Journalist: You had a parachute. Why didn't you?
Harold Krenshaw: It happened so quick. I wasn't thinking. Next time, I'll know better.
Journalist: So there will be a next time?
Harold Krenshaw: I'd better not say. Are there any cops in here?

Harold Krenshaw: Adrian? I knew you'd come. Can I talk to him? It'll just be a minute.
Nurse: Oh, I can't say no to the Frisco Fly. Two minutes.
Natalie: I'll be right outside. Bye, Harold.
Adrian Monk: So The Frisco Fly, huh?
Harold Krenshaw: Uh-huh. You look surprised.
Adrian Monk: I am surprised. Here's the thing I can't figure out. You look surprised too.