JESS: You’re gonna be an overseas correspondent? … You’re gonna crawl around in trenches and stand on top of buildings and have bombs going off in the background and some wars raging all around you?
RORY: What, you don’t think I can do it?
JESS: No, I do. Just sounds a little too …. Just sounds a little too rough for you.
Jess is the first person to suggest that Rory doesn’t have what it takes to be a foreign correspondent or war correspondent, like her hero, Christiane Amanpour. He’s not trying to put Rory down, and he specifically says that she is capable of it, he genuinely doesn’t think it’s a good fit for her, or be something she’d enjoy.
Of course, he’s right – Rory has led a very sheltered life in the safe haven of Stars Hollow, and according to Lorelai, hates the outdoors so much she wouldn’t walk on wet grass until she was three. And Rory actually met a journalist who travelled to dangerous international locations, Rachel, and she doesn’t seem to have bothered even talking to Rachel about it.