Guy's, read this, you need to understand the last scene of the ending.
RORY IS PREGNANT. Is it Logan's? Yes, it is. BUUUUUUT People are missing that this is a metaphor for "cycle", where Rory mirrors the situation in which Lorelei went through.
FIRST. Lorelei always said that as a rebel teenager, she used to think she could do anything if it not were for her parents, so in a series of rebellious acts, she ended up getting pregnant,, and after that it is that her character finally starts growing up, but we never got to see what would it have been if she never had gotten pregnant. On the other hand Rory had it all, the support of her grandparents with the benfit of not having to live with them (for starters), but on the contrary to Lorelei, she got a hard time growing up and being more mature, as with the time it became a clearer and clearer she had personality issues that might turn out to be issues that normally should have been resolved by teenagehood. So at the end, in a "cycle" metaphor and the "circle of life", she ends up as her mother, accidentally pregnant, refering than in her times of mother, mirroring Lorelei, she'll finally find her true Adult self and sense of responsibility.
Does this spread a sexist message? Yes. But it is a very sexist interpretation. But the show has been sexist before, and also, consider the show started airing in times were there was a much smaller social problems awareness.
SECOND. Since Rory's life's is supposed to have turned a different way than Lorelei's, both were meant to eventually catch up, and since Rory's is getting pregnant, it is expected she'd try to get together with Logan, him probably breaking up his engagement, but at the end, as with Lorelei and Christopher, Logan and Rory are not meant to be, and will eventually split apart, Logan may progressively dissapear for a couple of years, as Christopher, but will eventually come back to take responsability. Both guys are rebels, coming from very wealthy families, light spirited.
BUUUTTT That means that, if Rory doesn't end up with Logan, as Lorelei didn't with Christopher, it means Rory is going to end up with the one who always keeps coming back to her life and keeps connecting with her, so as Lorelei ended up with Luke, RORY WILL END UP WITH JESS!!
So, if you think about it, it's the logical way to go.
So with that in mind, Rory's story may be dissapointing for some, but it feels real, authentic, thousands of people go through situations like that in their lives and never live up to their potential. Still, people find their way to hapinnes and realization, and Rory may find it somewhere else, but at least, finally finding it.