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.

Dean Forester Quotes

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.
Dean: Yeah?
Rory: Yeah, it's my first Melville.
Dean: Cool.
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.
Rory: Me?
Dean: Yeah.
Rory: When?
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.
Rory: What?
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)

Gilmore Girls Quotes

Luke: Me? Raising a kid? I don't even like kids. They're always sticky like they've got jam on their hands. Even if there's no jam in the house, somehow, they've always got jam on their hands! I'm not the right guy to deal with that. I have no patience for jam hands!
Lorelai: First of all, Jess is 17 so I think he's probably pass the jam hands stage by now. Second of all, you can do this. If you want to you are totally capable.

Lorelai: Rory, I love you. I would take a bullet for you. But I'd rather stick something sharp in my ear than go to the club with you.
Rory: Fine.
Lorelai: I'd rather slide down a banister of razor blades and land in a pool of alcohol than go to the club with you.
Rory: I got it.
Lorelai: Don't stop me, I'm on a roll. I'd rather eat my own hand than go to the club with you. Ooh, I'd rather get my face surgically altered to look like that lunatic rich lady with the lion head than go to the club with you.
Rory: Would you like me to drive so you can continue your diatribe?
Lorelai: Would ya? Thanks. I'd rather cut off my head and use it as a punch bowl than go to the club with you.