Tim: Julie's t-shirt?
Natalie: That's what this whole thing has been about.
Tim: Her t-shirt? I don't understand.
Natalie: Tim, I've been waiting a long time to say this. Here's what happened. We know Dewey Jordan has been here. Mr. Monk noticed some game coupons in his apartment. Rob Sherman and Dewey Jordan met a couple weeks ago at the courthouse. Sherman probably told Dewey he was pulling some kind of insurance scam, but they had to meet again some place to work out the details. They met here at the pier. It was perfect; noisy, a big crowd, nobody would notice them.
Tim: But I don't understand, what does all this have to do with Julie?
Natalie: It was the same day you and Julie were here getting your picture taken.
Tim: Our picture?
Natalie: Exactly. The photographer had you pose right over there. But there were other people standing behind you. That's where Mr. Monk had seen them together. On Julie's t-shirt. They were in the background the whole time.
Tim: That would make sense. That's why he was acting so weird that day we met him.
Natalie: When Mr. Sherman saw that t-shirt, he knew he was in trouble. He saw Julie hanging out with Mr. Monk, the Captain, and Randy. It was only a matter of time before somebody noticed it.
Tim: I know, but why didn't he just try to steal it?
Natalie: Much too risky. Remember, he didn't have to destroy the shirt. He just wanted Julie to stop wearing it. So he had his girlfriend contact Clay. She pretended to be Julie's Aunt.
Tim: I get it. Julie breaks up with me and she never wears the shirt again.
Natalie: She's right, you are pretty smart. That's why we're here. The Captain's getting a search warrant. The photo booth keeps backup copies of all the pictures.
Tim: Uh, copy? Why- Why do you need a copy? Where's the t-shirt?
Natalie: Julie burned it.
Tim: She what?
Natalie: Sorry.

Natalie: Mr. Monk, please. This is important to me. Julie loves you. You're like family, you know that.
Adrian Monk: Just I can't- I just can't. Why don't you ask the Captain or anybody else. When it comes to this particular issue, I'm probably the least qualified person in North America.
Natalie: That's what makes you perfect. You waited for Trudy. You were faithful. You respected her. You're a wonderful role model.
Adrian Monk: Huh?
Natalie: In this particular case.
Adrian Monk: Why don't you just give it a few weeks? See how it goes. I always find doing nothing and never mentioning it again is always the best policy.

Julie Teeger: What's going on?
Adrian Monk: She wanted me to talk to you about... Certain things about life. And, uh... And things... [whispers] She's right out front. [loudly] She thought it might be helpful if you had someone you could talk to. [whispers] I'm supposed to be giving you the big talk.
Julie Teeger: [whispers] Why?
Adrian Monk: Because you're dating an older boy.
Julie Teeger: No, I mean why you?
Adrian Monk: That's what I said. [loudly] See, Julie, the years between 14 and 32 are a very confusing time for a young girl.