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They were all teens (and young adults) on the show, so of course they were all bound to make plenty of mistakes, and they did. And this also isn’t to say that I totally hate Jess, because I still enjoy him to an extent.But of all of Rory’s beaus, I find him to be the most toxic, borderline-abusive jerk of them all.
Lorelai won’t say anything, both of them treat it as a competition rather than a form of treatment.
On the love life side of things, falling back into Logan, falling back into an illicit affair, is the easy, comfortable thing for Rory to do, despite her relationship with Paul (seriously poor Paul) and her experience in this particular area (poor Dean).
It’s telling that the first time she lets her guard down to experience sex in a different way (even with a guy dressed in a costume), she realizes that her life is spinning out of control.
For Rory, it means stopping coasting along through life and jobs and relationships and slowing down long enough to figure out what it is she wants. Lorelai has spent her whole life hiding what she really feels after growing up in Richard and Emily’s house, and it’s destroyed her relationships before.
Rory has had one opportunity after another handed to her over the years, allowing her to succeed with little effort.
Considering the amount of stock both of these people place on honesty, this won’t go well. Rory’s problem is the expectation that things are going to come easily or be handed to her.