And then he'd do something terrific, so you knew he cared about Willow and Buffy, but that doesn't stop him from acting like a jackass. Even knowing about his family and making excuses for that it can be...hard to watch. I ended up cringing on Willow's behalf a lot these early seasons (which is one of the reasons I haven't rewatched them recently, I think.)

IRYJ has that scene near the beginning where Willow asks Xander if he'll stay late with her at the library, which in Willow-speak is the equivalent of asking him to stay late at the park and neck, and he laughs at her "Are you kidding?" Her reaction - ouch.