Question: when do rory and dean break up the 2nd time?
Answer: Dean sees her point and realizes he's been crowding Rory, and he pulls back. In the 18th episode, however, Lorelai finds him on their porch where he simply says, "She likes Jess, doesn't she?" In Season 3, Dean breaks up with Rory at a 24-hour dance marathon the town is hosting.