After winning Rory's charity basket ("basket, basket-maker, guy who didn't bring enough money"), Rory convinces Jess to give The Fountainhead another go, even though Jess thinks Ayn Rand is "a political nut" (Rand and many other Objectivists at the time were party to the 1950s Red Scare. She was also rejected anarchism, which is also probably why Jess has beef with her). Also the scene where Jess finds Rory's bracelet.