TROUBADOUR: ‘Cause you left me twistin’ for a long time before you did, Taylor, and it didn’t feel good. I even wrote a song about the experience.
LORELAI: Oh, I heard it. It’s called “Taylor Left Me Twistin’.”
The Troubadour writes songs based on his own experiences in Stars Hollow, and Lorelai and Rory have listened to this one, even offering the Troubadour encouragement, feedback, and advice as to what to add to the song. Apparently they, and perhaps others, are on friendly speaking terms with the Troubadour, even though in the show people just walk right by him. We never see him perform this song in the street, or anything else so personal, but that might happen off camera.