The "Die, Jerk" episode (S4 E8)
This is a Daniel Palladino-written episode. I find it interesting because I think it has multiple levels, which aren't always picked up on. For example, Scott Patterson's podcast didn't seem to notice some of them.
In this one Rory is attempting to get a regular gig with the newspaper, but it's not going well. Her editor, Doyle, keeps rejecting her articles, because they are "yawns". Having received nothing but praise all her life, Rory is kind of stunned. Her next assignment is to review a ballet performance. Lorelai comes along to join her. Together they make witty but rude comments about the performance, particularly Lorelai. (This kind of thing would happen again in the Summer episode of A Year in the Life, also by Daniel Palladino. It is one of the most criticized scenes in the new series.)
Rory writes up her review and lo and behold, Doyle thinks it's great and sends it off to be published. But only the careful viewer seems to notice that what Doyle loved were all the clever comments thought up not by Rory, but by Lorelai. Of course Lorelai is fine with Rory plagiarizing her ideas, but the problem is it appears Rory does not herself have the talent necessary to be an interesting writer. Only when Lorelai feeds her witty ideas is an article of hers able to reach an acceptable level.
Later at the Friday night dinner, Rory's grandfather Richard makes a relevant comment. It seems he and his wife Emily had read (and enjoyed) Rory's review of the ballet. Richard makes a comment about the ballerina: "Sometimes people at a young age don't know that they're not good at doing something. Now that poor girl can go to business school." The thing is, and though it does not register with any of the characters, including Richard, this completely applies to Rory. She also is not good at what she is doing, does not know it, does not know how to go about addressing it and is not helped by her parents and grandparents who do nothing but praise her.
When later in A Year in the Life we see that Rory has only had middling success in her career, at best, we can look back to this episode as the first sign of it. That she works very hard and checks all the boxes, but lacks that special quality of imagination or understanding that would make her a great writer.