
Note: As a diehard Monk/Natalie shipper, I’ve decided to relive the series by highlighting some of the best moments between the two characters. Not all of these scenes are “shippy”, especially in these early seasons. But they’re cute or funny or represent “firsts” that foreshadow the closeness that will develop over the course of the next few years. I’m listing them chronologically because Mr. Monk wouldn’t want it any other way!
Episode 4×12 — “Mr. Monk and the Captain’s Marriage:” This episode was memorable to me because of how much time M/N spent together. Instead of Natalie just being in the background of for most of the scenes, it felt as though she had more dialogue with Monk. The professional partnership seems to be deepening.
- (16:10) — The whole scene where they’re following Karen was fun, from Monk giving Natalie tips on how to trail someone, to their casual touches, banter (“I know not you, but people.”), and of course the mannequin. It was just fun!
- (21:32) — The fountain scene was terrific, too. Monk looked so sincere and stricken when he said the three extra pennies would “haunt” him, lol. I also really liked Natalie’s expression at (22:28) when she gives in to him and pulls out the three pennies.
- (25:57) — Monk: “Natalie, don’t touch him! Later on if we have time, I’ll tell you a little story about the BLACK PLAGUE!” (Pictured above.) OMG, so funny!!!
Episode 4×14 — “Mr. Monk and the Astronaut:” (There weren’t any M/N scenes worth mentioning in episode 4×13, so moving right along….) Jeffrey Donovan playing a smarmy bad guy? I only know him as Michael Westen, but he was believable as the arrogant astronaut murderer here. There weren’t many good M/N moments to choose from in this one, but here are a few cute ones.
- (4:06) — “Actually, there were a couple of things that I didn’t mention. I didn’t want you to think I was weird.” Monk, explaining to Natalie why public speaking is a phobia even though it wasn’t on the original list of 103 fears that he gave her when she started working for him.
- (4:24) — Natalie briefly puts her hand on Monk’s shoulder because she knows the terrible smell of the crime scene will get to him.
- (5:05) — Natalie gives Monk a cute little smile when he figures out what “between the sheets” means (pictured below).
- (18:59) — Natalie straightens Monk’s lapels and gives him a reassuring nod before he starts speaking at career day.
- (35:23) –Monk stops to fiddle with some warheads. Natalie: “No, no, no, no… they could be nuclear weapons!” Monk: “Then stop me, for the love of god!”

