Jess is carrying this 1957 book by American Beat writer Jack Kerouac, previously discussed, when he leaves the diner. It looks as if Jess might be looking for a quiet spot to read, just as Rory likes to do.
It immediately establishes Jess as a reader, something which will surely pique Rory’s interest, as she was always trying to get Dean to enjoy great literature (with unsatisfying results). It is also an obvious symbol of Jess’ journey to small town America, and possibly a foreshadowing that Jess does not intend to stick around.
The Annotated Gilmore Girls 
5 thoughts on “On the Road”