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And yeah I always felt like they went a bit overboard with writing Emily as the villain in season 5, I know that she would have preferred Lorelai to be with Christopher, and I could buy her acting like a snob at the dinner with Luke, but it just didn't seem in character for her to actively scheme to break Luke and Lorelai up. If anything she was always very aware of not doing anything that might drive Lorelai away. I was surprised at Luke wearing jeans to FND though, you'd have thought Lorelai might have mentioned that they were quite fancy affairs, and he needed to dress up more than that. But then he was wearing his baseball cap and flannel to Richard's country club, so at least he lost the hat for FND I suppose  |
I feel like Luke wanted them understand that that was who he was and he didn't need to become someone else to be with Lorelai, that's not what she wanted. Lorelai was happy with Luke the way he was (even though he dresses like a lumberjack most of the time). It wasn't about money or class, it was simply about love. It's also just possible that he really didn't care. We have seen Luke dress up on the occasion for important things.