DEAN: Hey, you wanna get a cup of coffee? … Maybe talk a little? Of course, if you prefer, we can both just head over to Weston’s and randomly bump into each other.
RORY: No, uh, that’s okay. I can get coffee.
While Rory is browsing in the window of Stars Hollow Books, she runs into Dean. Apparently, they have been “randomly” bumping into each other for some time now. And if you believe that, then I’ve got a mighty nice bridge for sale!
The upshot of all this creepy stalking (I mean innocent random encounters) is that Dean asks Rory to have coffee with him at Weston’s Bakery – Luke’s Diner being out of the question for obvious reasons.