- Pacey: You know, this town is the absolute embodiment of dull. Apart from the occasional sex scandal provided by yours truly, nothing happens here.
- Dawson: [describing heartbreak] It's agony. Complete, excruciating agony. It's like your heart has been ripped out of your chest and stomped on, and you can't breathe... you don't want to eat... you can't function. It's the most intense pain that you'll ever feel, and the worst part is, there's no way to relieve it. It's unyielding, merciless torture, and you *know* that it's yours for life.
- Joey: Dawson, I'm sorry I don't have the same dreams I had when I was 15 years old, and I'm sorry that I moved on faster than you did, but you know what? Maybe not everything that happens to you is my fault! And maybe just because I want more from my life than...
- Dawson: More than what? More than us? You don't know, do you? You've never known. The entire time I've known you, all you've wanted to do is escape. From me, from Capeside. I mean, you say that I'm the dreamer. I'm the one who doesn't wanna live in the real world. Well, I'm doing it, Joey. Right now. I'm living in the real world. It's you who wants the fantasy
- Joey: You know, I have asked you six questions tonight and you haven't answered one.
- Jack: Well that's because you have to ask me seven. See seven is the magic number.
- Joey: There you go again. Why do you make light out of everything?
- Jack: Because I am aloof, introverted, and unsociable so there, I answered one.
- Joey: I was scared.
- Dawson: Of what?
- Joey: Of going backwards, of never growing up.
- Dawson: That's what I represent to you?
- Joey: No, not you. Us. I started this year thinking that I had to say good-bye to you, but I was wrong. Dawson, you're a huge part of my life - past, present, and future - and I have to start getting used to that because... you make my life better, not worse
- Dawson: How can you be friends with someone when every time you see them you think about how much more you really want?
- Jack: I don't believe in perfect love. But I do believe that there are people who's lives are inextricably intertwined.
- [Grams runs into an old boyfriend]
- Evelyn "Grams" Ryan: I thought you were dead.
- Jennifer "Jen" Lindley: Great pick-up line.
- Pacey: I'm a better catch than Tye the Bible-beater or that skirt-chasing Neanderthal Chris Wolfe.
- Jennifer "Jen" Lindley: This coming from the guy whose past two relationships have ended with the girl either leaving town to avoid prosecution or cool out in crazy camp for the summer?
- Arthur Brooks: And remember, you're still young enough to fall in and out of love a few more times before you get it right.
- Dawson: That doesn't sound very fun.
- Arthur Brooks: It isn't... And it is... And it isn't. But it's worth it. Every single time.
- Joey: Do you believe in magic? I never used to. I mean, how could I? 13, your mom dies, you hope against hope for magic, something to make it all better. It never comes, and, you know, you look to your father who's unable to overcome all of his tragic flaws. Well, no abracadabra there. And then there's Pacey. Well... any magic that was there, that ran out, didn't it? But, uh, then there's you. There's proof that someone out there is thinking of me... my friend who was with me always. It's pure magic.
- Joey: So the friendship? You don't think we're friends anymore?
- Dawson: I don't know. Are we more? Are we less? All I know is it's just not the way it used to be. Nothing is anymore.
- Joey: It's called social evolution, Dawson. What's strong enough flourishes and what doesn't we look at behind glass cases in science museums.
- Dawson: You and I? Are we museum bound?
- Jennifer "Jen" Lindley: Hey, Joey, I love your lipstick. What shade is that?
- Joey: Wicked red. I love your hair color. What number is that?
- Joey: When I saw you going for Jen's hand... it's not like I wanted to be the one holding your hand. I just didn't want her holding it.
- [Dawson insults and drives away a film critic]
- Oliver Chirchuck: Apologize, kiss her ass, get down on your knees and beg, just do whatever it takes to get her back here.
- Dawson: Alright, alright. What are you going to do?
- Oliver Chirchuck: I'm gonna go and hit on your ex-girlfriend.
- Mr. Kasden: [reading from a book] "Near the end of March, 1845, I borrowed an axe and went down to the woods by Walden pond. Nearest to where I..."
- Mr. Kasden: What's the most important word in that sentence?
- Joey: Woods?
- Mr. Kasden: Borrowed. The important thing to remember about The Transcendentalists, is that while self-reliance is a most admirable trait, Thoreau wasn't really all that alone out there by Waldon pond. He had neighbour's, friends, people he could rely on. We should all be so lucky.
- Abby: Getting a sexual confession out of Jen Lindley, that's like getting Bill Gates to admit he made two dollars last year.
- Joey: Cramming dreary German folk tales and the inner workings of the Fett is hard enough without having to listen to a diatribe about your ass.