[Jess is reading on a bench as Rory walks up behind him]
JESS: How ya doing?
After all the effort Rory has made to come to New York, apparently on a whim, she seemingly just walks in a side gate of Washington Square Park and finds Jess straight away (Rory is looking pretty fresh for someone who’s been on a bus for hours and just had a long walk). He’s sitting helpfully on a prominent park bench right at the entrance. It is now presumably somewhere between midday and 12.30 pm.
I know Jess was very lucky, phoning Rory when Lorelai was drunk and had the stereo on loudly so they could talk in private, but it’s nothing to Rory’s luck in finding Jess! All she had to go on was that he often hung out in Washington Square Park, and without making any plans to meet at a particular day, place, or time, it looks as if she turns up and Jess is right there. I mean, even if Jess was in the park, it’s ten acres – it could take hours to search for him. And lucky he hadn’t gone to the toilet or to lunch just as she arrived!
It would have been more believable if Rory and Jess had some sort of agreement to meet in New York, but that would have made Rory much more sneaky, treacherous, and selfish. It has to seem completely spontaneous, so that the relationship between Rory and Jess can remain innocent.
None of the scenes in this episode were actually filmed in New York – they were all shot at the Warner Bros lot in California. This scene takes place in New York Park, Burbank. There is no side gate such as the one Rory walks through, and if she approached Washington Square Park straight down Fifth Avenue, she would come to the main entrance, with the famous archway. Needless to say, it doesn’t look like Washington Square Park, and the real park is far more crowded, especially on a sunny spring afternoon around lunchtime.