I actually get the impression Chris is trying far too hard to impress and make amends. As though he thinks making a big splash - the drive-in date, Paris, taking all Rory's YDN co-workers out to an expensive restaurant - will do it. Throw a ton of money out, and all will be fine. I don't think Rory and Lorelai will be impressed by it in the long run though, neither one of them is particularly materialistic, and no amount of money can make up for all the missed milestones in Rory's life. Guess he still has to learn that.