We can debate all day long about which of Rory's boyfriends on "Gilmore Girls" is really her best match, but when it comes to first kisses, it's hard to argue with the Rory/Jess pairing. A full season of bickering friendship and high drama all lead up to this moment when Rory, surprised to see Jess returned to town, impulsively kisses him — before running away in a most Gilmore way.