Dean Forester is the new guy in town and falls had for Rory Gilmore quickly after she shows him around Stars Hollow. Despite being from different social classes and going to different high schools, Dean and Rory date for much of the beginning of Gilmore Girls. Dean even tries to date Rory during her Yale career but it doesn't work out due to their different places in life.
Rory: That's my mom!
Dean: She's got energy.
Rory: Yeah, well, she's 90 percent water, 10 percent caffeine.
Dean: So, how are you liking Moby Dick?
Rory: Oh, it's really good.
Rory: Yeah, it's my first Melville.
Rory: I mean, I know it's kind of clich to pick Moby Dick as your first Melville but hey, how did you know I was reading Moby Dick?
Dean: Uh, well, I've been watching you.
Rory: Watching me?
Dean: I mean, not in a creepy, like, "I'm watching you" sort of way. I just - I've noticed you.
Dean: Every day. After school you come out and you sit under that tree there and you read. Last week it was Madame Bovary. This week it's Moby Dick.
Rory: But why would you
Dean: Because you're nice to look at, and because you've got unbelievable concentration.
Dean: Last Friday these two guys were tossing around a ball and one guy nailed the other right in the face. I mean, it was a mess, blood everywhere, the nurse came out, the place was in chaos, his girlfriend was all freaking out, and you just sat there and read. I mean, you never even looked up. I thought, "I have never seen anyone read so intensely before in my entire life. I have to meet that girl."
Rory: Maybe I just didn't look up because I'm unbelievably self-centered.
Dean: Maybe, but I doubt it.
Rory: So did I ask you if you like cake?
Dean: Yeah, ya did.
Rory: Oh, because they have really good cake back there. (Dean laughs)