This is the song which plays while Rory and Jess walk through the streets of New York to get a hotdog and then go to the subway. It’s a 1992 song by Yoko Ono, first released on Onobox, a comprehensive 6-disc collection of Yoko Ono’s work from 1968 to 1985. It included 20 previously unreleased songs, of which “O’Oh” is one.
The lyrics are about a couple enjoying the Fourth of July celebrations in Central Park together, so it’s a song about New York. Some of the lyrics are:
I never thought we’d be laughing together
I never knew life could be sweet and simple
I never thought that was possible
Not only does the song suit the setting they are in (although it’s May, not July, and a different park), but the lyrics are about how Rory feels about Jess. The surprise of finding that being with him is not only sweet, but simple – you can feel how easily the two of them get along, how effortlessly they laugh together.
Rory finally gets to meet Jess away from Stars Hollow, and he’s not surly, not bitter, not sarcastic – he’s sweet, he’s nice, he’s funny, in a way she never thought possible. She has taken any number of practical, physical, and emotional risks to come to New York to see him, and she gets the softest of landings, as Jess finally opens up to her, now that he’s received unexpected proof of how much Rory cares for him.
There is a real flipside feeling to the choice of song, because when Rory had her sweetest and most romantic experience with Dean (sitting in the car wreck on their anniversary), the song chosen to accompany it was by John Lennon. Now her sweetest and most romantic scene with Jess is accompanied by a Yoko Ono song. (Both songs have Oh in the title, also).
It is as if Jess and Dean are her Yin and Yang – Dean the Yang which complements her, and Jess the Yin which matches her. With Dean, there is an attraction of opposites; with Jess, an attraction of like minds, or twin souls.