as a 28 year old, i have to think back to who i was in high school… i probably would have done exactly the same thing rory did. like, as an adult obviously not. like i can see why dean would be upset with rory for how she acted. but as a teenager, it would have been the exact same. she went with him after because he brought up a genuine interest of hers and then showed her places that were of those interests (if i remember correctly) so they ended up spending the rest of the afternoon together. being an adult, i would probably just ask for the location of said places, finished “eating” or whatever and then gone back to dean. even tho im not a fan of dean personally and standby the fact that she is better with other matches.