JESS: Okay, tomorrow I will try again, and you will . . .
RORY: Give the painful Ernest Hemingway another chance. Yes, I promise.
JESS: You know, Ernest only has lovely things to say about you.
Ernest Hemingway (1899-1961), author, journalist, and sportsman. He is famous for his economical and understated style, which had a profound influence on 20th century fiction, while his public image and adventurous lifestyle brought many admirers. He produced most of his work during the 1920s to the 1950s, and was awarded the 1954 Nobel Prize for Literature. Many of his works are considered classics of American literature.
Hemingway’s hard, lean prose style and strongly masculinist ethos (to the point where it sometimes seems misogynistic) seem at odds with the more diffuse, subtle writing that Rory seems to appreciate. The irony is that Hemingway was a journalist, which helped to hone his spare writing style.
I’m not sure exactly what Jess means by “Ernest only has lovely things to say about you”, but in his works, brunettes are usually good, while blondes are bad (hm, rather like Gilmore Girls). Hemingway married four times times, three times to fellow journalists, as Rory plans to be.
The Annotated Gilmore Girls 
Can I just say firstly that I love this blog so much! It’s very enlightening to me as a younger, non-American first-time viewer over whose head fly like 80% of the references lol. I love your analyses of the characters too 🙂
In this scene, I think Jess was jokingly acting offended on Ernest Hemingway’s behalf, as if he knew him personally and Ernest had said good things about Rory. Like a reversal of the classic “I hate maths” “Well, it hates you too” type of comment that my friends and I so wittily throw at each other haha. Ngl it’s a pretty good pick-up line for a bookworm like Rory.
LikeLike
Thank you! That makes sense.
LikeLike