"Star Crossed Lovers and Other Strangers" (s1:e16) introduces us to The Firelight Festival- the annual celebration of the birth of Stars Hollow. The infamous Rachel returns. And in a totally cliched teenager move, Rory and Dean celebrate their 3 month (gag me) "anniversary" (note the quotes... the "anni" in "anniversary" stands for annual. This was a monthiversary... and monthiversaries are effing ridiculous. Fucking teenagers, man. End rant) and then break up in a dump (oh the irony of being dumped in a dump).
Because youtube hates me, here are some stills from this episode: