Oh. I can't pick 5. Only 3. Lindsay, Jess, and Christopher.
Why?
Jess:
1. The most obvious reason (for me): He got in the way of my favorite pairing; Narcoleptic.
2. He was only nice to Rory. (Yeah, I know that can also be a good thing. But it's a bad thing too.)
3. He always stole things from other people, and had to be talked into giving them back. (And sometimes he never did.)
4. All he did was run away, not caring at all.
5. He wanted to have... umm... well... I probably shouldn't say that, but I think you know what I mean... with Rory, when she felt most uncomfortable with doing that.
6. He was always skipping school. And when he wasn't, he was getting into a lot of trouble.
7. He got Rory hurt with his driving 'skills'.
8. He made Rory skip school. Rory never skipped school before, but he somehow made her skip.
9. He always seemed to want to get rid of Dean. (I know that would probably go along with reason 1, but still.)
Lindsay:
Only two reasons for now, but still.
1. Again, the most obvious reason; she got in the way of my favorite pairing; Narcoleptic.
2. She made Dean (okay well I guess she didn't MAKE him since he went along with it, but still.) marry at such a young age.
Christopher:
CHRISTOPHEEEEEER! I hate him!
Agreed.
1. He seems to care about Rory more than Lorelai.
2. I don't know if I'm the only one who noticed but at one point I seem to remember him being a two-timer.
3. Because he skipped Rory's graduation ceremony.
4. Because he ignored Rory's request to stay away from Lorelai.
5. Because he cares more about money than his grandfather dying.
And so, so many more.
We can rebuild it. We have the technology. We have the capability to build the world's best Gilmore Girls forum. The ORG Forum will be just that. Better than it was before. Better, stronger, faster. 
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