Is there something I'm missing about Jess?

I recently rewatched the earlier seasons and while I was once an avid Jess supporter, I couldn't find the appeal of him the second time around. I liked his relationship with Rory more than I did him, I don't care for Jess' arrogance and disrespectful attitude. I prefer him over Dean and Logan and I definitely think Jess makes up for his attitude later on, but it'll be a while before you get to that point in the show.

I agree with much of your assessment of Jess. He does get better, though, after he moves out on his own and matures. We only see him occasionally later on, but he reconciles with Luke and his mom and has some success as a writer. He and Rory stay friends.

Dean and Logan, for all their faults, treated Rory much better. Jess was a terrible boyfriend.

I totally agree.. I always felt he was a jerk..

Yes - he kind of does have a personality change later in the series.
Though I agree with you - I don't get the Jess-appeal! I mean he grows on you a little bit, but I don't get all the crazy shippers out there. I also never liked how Rory treated Dean once he showed up!

You're going to suffer...but you'll be happy about it!

I get the Jess appeal as in he was the most fully fleshed out of Rory boyfriends, and he had the most complete arc and it was fairly redemptive (you have to watch the rest of the series). Also, Alexis and Milo had solid chemistry. The reality is I don't care for any of Rory's main suitors. However, Jess if the best for me if only because he's the only one that seemed like a real person instead of just "the boyfriend".

I think Jess is mostly attractive to girls at rebelling age, I think around 14 to 22. That is when they think grown ups are phony and corrupted (the usual environmental terrorist phase).

So a smart ass boy looking down on the world, not following what adults told him to do and even being destructive seems refreshing and attractive, not knowing that is just about the biggest cliche there is.

That might sound condescending but I don't know to make it sound better and retain the same message.

A cynic is what an idealist calls a realist - Sir Humphrey Appleby

Everyone has their flaws and I certainly dont think Jess is without but with regards to assets:

1)Looks are subjective. I – as well as lots of other people – find him very attractive
2)He is intelligent, perhaps not fully emotionally, but in general he is quick witted, well read and is very good at reading other people (often to his own advantage, such as to mess with Dean for example)
3)He has a vast interest in culture, books in particular –whether or not you buy it is not really the point, that was how the character was written so it’s a fact.
4)Again, charisma can be subjective. He was also funny and genuinely cared about both Rory and Luke when it came to it. Granted he made mistakes but this is a 17 year old boy we are talking about. Added to that his scenes with Rory were just packed with chemistry between them (no doubt to do with the fact that they also dated in real life). That’s the beauty of chemistry between two people, it doesn’t really have to make sense to anyone else but them.
5)I don’t think he is nihilistic. He finds meaning in books, music and in relationships with people he cares about, albeit there are very few of those. Again, I think a lot of people disregard the fact that he was a teenager in the show. A lot of teenagers are moody, sarcastic and far too cynical for their own good. I would hope they don’t get judged on that for their entire life.

I read a lot about how Jess treated Rory badly. But as far as moral principles go, at least he made it clear he had no desire to pursue anything further than that first kiss with Rory until she broke up with Dean (referring here to the argument at the grocery store). Whereas she somehow expected they would pick up where they left off when she returned whilst not showing any plans what so ever to break it off with Dean. Added to that Jess made sure to break it off with Shane before he got together with Rory.

No doubt the guy made mistakes, but I think ASP made a pretty good job in demonstrating why Rory, and many other girls her age, would still have an interest in him.

I can certainly buy that not everyone likes Jess personality. But hey, do you really think Jess is unattractive ? Have you even looked at him?
I can only speak for myself, and maybe my friends who also dies when they see him , but god the guy is so damn good looking. I could drown in his beautiful brown eyes. Super hot, I 'm just saying ...
There is nothing I can understand more than why Rory would be attracted to him by his look. The first time she met him , she must surely thought about what bombshell he is? Such a handsome nugget in your room,
I would literally die. But even more , I can understand why Rory is attracted to him when she gets to know him.
For me he is the hottest and the most good looking guy in the show, plus he has the most interesting personality.