I’m going to ramble about Chris.
I think his character showed much growth, as Dani pointed out, but it was zig-zag in a typical tv show sort of way, especially because he was a supporting/recurring character. I think the writers utilized him as they saw fit in his relationship with Lorelai and Rory and that made his character at times a bit sketchy for me. I saw this right from the start: The background is that Chris was willing to marry Lorelai when she became pregnant and do the old-fashioned “right thing”, but Lorelai turned him away. In the pilot episode, Richard talks about him as being successful in business on the west coast, going public with some vague Internet company. But by the time he appears in person, he is the guy on the motorcycle who is portrayed as unreliable and immature, Rory yearning for attention he only gives sporadically, and Lorelai is waiting for him to get his act together. So you might say there was a shift in Chris’ character from the moment he appeared, based on what we were previously told.
About Rory’s early upbringing, it has never been clear to me if Lorelai kept Chris away or if he chose to stay away or if it was mutual. But it’s always seemed like Lorelai with Rory against the world, and Lorelai was not inviting Chris in. Perhaps after Lorelai rejected marrying him and ran off to S.H. with Rory, Chris himself realized he was not wanted and went about his own life. Maybe it was their unspoken understanding.
I’ve sometimes had mixed feelings about Chris but he really didn’t do much that made him a bad guy. His detractors love to criticize him for running off to Sherry in “I Can’t Get Started” just as he and Lorelai were about to give it a go (another season finale plot twist). But I’ve always thought he deserved credit for – again- trying to do the right thing. He explained to Lorelai that he wanted to make up for what happened the first time. I personally don’t think he did anything wrong the first time (except being careless enough to get Lorelai pregnant of course), because he was willing to marry Lorelai and be there for her and baby Rory. Did he feel guilty about that whole thing despite his attempt to do right? Was he looking at Sherry’s pregnancy as a second chance to be part of a new family? I think so and I don’t fault him for that.
One big moment for Chris came after Rory had the car accident with Jess. He showed up, became involved, and when Lorelai asked about Sherry, he said that Rory comes first. But even before then he had become a more reliable dad. When Sherry first appeared, she said how Chris never misses his regular phone call to Rory and talks about her constantly.
Although I think Chris’ low point came in season 5 during the “Wedding Bell Blues” mess, even there he had some sympathy about him. I like the scene in that episode where he tells Rory about the first time Lorelai kissed him, the fact that she made the move. He said it was the greatest day of his life. Nice moment.
Although I tended to root for Luke, during season 6 I found myself rooting for Chris during the April mess, when he was the guy on the spot for Lorelai. I thought he came across really well at the Lane/Zach dual weddings, and also the ep where he joined Lorelai to watch Rory’s journalism debate. I never knew the term “shipper” before joining this forum, but I might have been a Lorelai/Chris shipper during this period, when the writers seemed to be saying “Luke is a jerk and Chris is the good guy”. During the “Wedding Bell Blues” mess, when Chris was under Emily’s spell, the message seemed to be the opposite. Or, at the very least, he was a misguided desperate person in need of a reality check.
When Chris and Luke had their gladiator fist-fight in season 7, Chris had more of a legitimate reason to fight. He was the one who was married to Lorelai. Luke had his shot and blew it. If Luke was pissed at anyone it should have been himself, not Chris.
About Chris not appearing at Rory’s Chilton graduation, i think the writers could have handled it differently and easily allowed his appearance with minimal disruption. The characters could have behaved like grown-ups for a few hours for Rory’s sake. This was Rory’s big day and they could have obliged her about that. I mean, she is graduating from this hoity-toity school as valedictorian, makes a big ol’ speech, and dad is not there? Instead, the writers did the tv show thing of blurring over it as though his absence was nothing. Rory did not seem to notice or care. Even Emily didn’t seem to give it much thought when Lorelai gave some flimsy excuse.
Chris’ character ended the series on a high note. His final appearance in “Unto the Breach” showed he and Lorelai at a new understanding in their relationship. The marriage didn’t work out but there were no hard feelings and, with Rory as their bond, they could carry on a good relationship. Never mind that the continuity from their failed marriage didn’t add up (when exactly did they decide to happily move on?), it provided a nice finale for Chris and Lorelai. They seemed to come full circle and found a way to be comfortable with each other, free of any soap opera explosion on the horizon.