I think the fact that Chidi was so upset over that lie also foreshadows his flaws. After all, it seems pretty ethical to me TO lie about such a thing. If someone says "be honest", don't be honest. I mean, sure if Henry was going to wear the boots to a funeral, Chidi might have been better off advising that it wouldn't be appropriate. Or if Henry was going to wear them surfing, pointing out that they might be slippery. But he couldn't handle the fact that he was dishonest to spare someone's feelings. And that's a pretty big oversight, as much as I love Chidi.

Good point about Eleanor's growth. She didn't magically change overnight, but she was willing to help a friend.