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IMO Amy wanted to show Rory and Logan in one of those casual college relationships: they had fun together and they even challenged each other a little bit (in a good way), but they didn't really consider anything longterm. There was no atmosphere "the greatest love of my life" (at the beginning).
Stealing a boat? It's a very problematic behavior IMO. If someone else did it (difficult male like Jess), they could arrest him for quite some time.
What happened to Rory? Lack of Lorelai's and grandparents supervision? Logan's influence? Influence of new friends? Rebelliousness against Lorelai?
I don't know. But I would really like to discuss about it.
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Sorry about the dp but had trouble getting this to work.
A lot of the change in Rory is down to Logan's influence. In truth the GG have always had a self-centreed trait and Rory, for basically her entire life, has had the town she lives in worship her and think she could do no wrong - it was bound to go to her head at some point. But Logan and his ilk were perhaps the first people she was awed by and that didn't worship her - I think Logan often made her feel inadequate, certainly in the beginning and his family definately added to that. She got swept up by him and his ways. Logan and his friends saw the world as their personal playground and treated everyone in it as though it was and everyone else was merely a guest. Rory has maintained that mentality in some ways. I think she sees her former boyfriends as still hers - she certainly has no problem cheating with them, knowing full well that they are in serious relationships - even marriages. It's as if these other women have no thoughts or feelings. I think she was genuinely shocked to learn Logan's fiancee had moved in with him - as if until then, his fiancee wasn't even real until she was physically invading Rory's world and making life inconvienient for her - despite being engaged to Logan, it was impossible for Rory to even remotely consider the fact that Logan could love this other woman, even more than Rory. Logan cheating means nothing to him in a way - has he ever been truly faithful? Another woman moving in with him is what it took for Rory to start to wake-up and yet she still went along with him after her turned up in SH.
What does all that say about her now? I could maybe understand if I thought she was madly in love with him but it never felt like she was to me. If she was - why didn't she fight for him? Answer - because she didn't want him - at least not on a perminant basis. While Logan sees the world as his playground - Rory sees the people in it as the toys in her playbox. Eventually, when a toy is used beyond all recognition she'll let it go - even smile to see it happy with someone else - such as with her Dean-doll. Rory, particularly in her personal life, is very much like a child.
A rather scathing review of Rory's character development, I know, but i have found so little to like about her since the college years really. Her decline, to be fair to Logan, did start before him but it deepened under his influence.