The season two finale is centered around Sookie and Jackson's wedding.  Christopher and Sherry break up and after spending a romantic evening with Lorelai, they decided to get back together... until he finds out Sherry is pregnant.  Rory is surprised to see Jess at the wedding and they kiss.

Gilmore Girls
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Gilmore Girls Season 2 Episode 22 Quotes

Paris: (on asking Rory to run for Vice President) Because people think you're nice. You're quiet, you say excuse me, you look like little birds help you get dressed in the morning. People don't fear you.
Rory: Hey, I haven't been dressed by a bird since I was two.

Dean: (Referring to Babette and Miss Patty singing) So, how many cocktails caused that?
Rory: Oh, they haven't had any cocktails yet.
Dean: Really?
Rory: Oh yeah, when they start having cocktails we're gonna have to hide you.