While Jess is in the kitchen being introduced (he never bothers to greet Sookie and Jackson), he notices that Rory’s bedroom door is open, and just as he quietly slipped into the living room without being invited, he now wanders into Rory’s room. She is sitting with her back to the door, so she doesn’t immediately know he is there. As with the photos, he gets a chance to check Rory out without her knowing, and before she can look at him.
There is a parallel with Rory’s boyfriend Dean at this point. Both Dean and Jess were invited to the Gilmore home for dinner by Lorelai, and both of them went into Rory’s bedroom without asking, as a sign of their interest in her. Dean had been asked as a date for Rory, and they had previously kissed, but Jess has never even met Rory before. It’s a bold and presumptuous move to explore her personal space.
In case there is any doubt what’s going on here, Rory is wearing a cardigan decorated with pinkish-red love hearts, made to look as if they are the fluttering petals of flowers (fluttering heart, hearts and flowers!). The cardigan is buttoned up though, to show that this flower has not yet opened to Jess. Meanwhile, Jess has a large number 2 on the back of his (bad boy) hoodie. The show uses costume a lot to make a point, and in this instance, it seems impossible not to mention it.
Once again, Lorelai follows Jess to see what he’s up to, and this time she isn’t quite so smiling when she asks both of them to come to dinner. I think Jess can now count himself as being on Lorelai’s radar.