I thought Maid-san was very attached to supervisor-san, but she barely drops a tear. Of course, that's because writers are obsessed with making blonde female characters look strong and unfazed by life and they think to have those characters show real emotion makes them look weak. But as usual, that obsession makes for bad writing, because after seeing that happen to supervisor-san maid-san really should have been sobbing like any other character in her place would have.