Weirdly, when he really starts to get out of that box is when Faith arrives.
*cough*taughtacourseonthis*cough*--but it's no accident at all. The Faith arc deliberately contrasts the "appropriate" Slayer-Watcher relationship that Buffy and Giles have to the "bad Father" dynamic of Faith and The Mayor, a move that seems to me precisely calculated to bury the thought that Buffy and Giles could be romantically involved (despite the relationship looking exactly like the one in, say, Austen's Emma, where Buffy is Emma and Giles is Mr. Knightley.) That was something they wanted to disown, and so as so often in the Buffyverse, it's done by way of dramatic foils. On Buffy, even the FOILS have foils-it's honestly more Shakesperean than any contemporary drama I can think of.
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*cough*taughtacourseonthis*cough*--but it's no accident at all. The Faith arc deliberately contrasts the "appropriate" Slayer-Watcher relationship that Buffy and Giles have to the "bad Father" dynamic of Faith and The Mayor, a move that seems to me precisely calculated to bury the thought that Buffy and Giles could be romantically involved (despite the relationship looking exactly like the one in, say, Austen's Emma, where Buffy is Emma and Giles is Mr. Knightley.) That was something they wanted to disown, and so as so often in the Buffyverse, it's done by way of dramatic foils. On Buffy, even the FOILS have foils-it's honestly more Shakesperean than any contemporary drama I can think of.