USW: The Truth Shall Set You Free
Rupert Blackmoor is the owner and manager of the bookstore Merciless Words in Chicago. He also happens to be a good friend of Jane Hathaway, no doubt due to her frequent patronage of his shop during her college days. He still assists her in her research at the Field Museum.
Image retrieved from http://dvdbash.com/2013/09/30/buffy-2013-gallery-09-rupert-giles-anthony-head-photos/ on April 30, 2015.