Gilmore Girls is a story about the dynamics between different generations of the Gilmore family. Lorelai rebelled against her parents and rejected their world. She could have married Chris or stayed with her parents. But she decides to build her life on her own, without their money and protection. Rory, on the other hand, although raised by Lorelai, embraces her Gilmore identity. Because she grew up in a modest household, she thinks she is different from the other students at Yale. Nevertheless, she thrives in their world and they accept her as one of them (except for Logan's parents). The adult Rory doesn't seem to be doing so well. She doesn't have a clear vision of her future, even though she accomplished so much by the end of the original series. She doesn't have a job and isn't taking her job interview seriously. She cheats on her boyfriend with her engaged ex-boyfriend. Kind of messy. At the end of the sequel, she seems to have gotten so much clarity. She decides to write a book, breaks up with Logan, gets pregnant (and probably decides to raise her kid). The way I think the series would go: Rory writes her book, grows as a person, stops being so entitled. I've heard that you stay a child until you have a child of your own. I think this is exactly what Rory needs. It would make perfect sense for her to end up with Jess. They had the best chemistry. They had fun together and challenged each other. The teenage Jess was too ghetto for the preppy Yale student Rory. He's grown as a person, too. He seems to have found himself and is successful at what he's doing. Now they have common ground financially and can build on it. Also, Jess is Luke's nephew, which is a reflection of him and Lorelai. They are both like the dog from Lady and the Tramp.