Dave is a friend of Darren's, and Cheryl was married to Dave.
Joe Caparo was a waiter at a pizza parlor in Chapel Hill.
Summer Burke is a friend of Ben's.
The Hardback Cafe was a popular hangout in Chapel Hill, mainly a coffeehouse and a pretty good lunch place by day and a performance space by night that often featured poetry readings and the like. At the time Ben wrote the song, the Hardback had closed and he figured they'd turn it into a nondescript chain store ("Office Town", because it rhymes with "closed down"). Actually, an equally cool joint called the Lizard and Snake opened at that address (110 N. Columbia), a neighborhood bar and gathering place which hosted much live music. It, too, has since closed (1998) and became the home of a Japanese restaurant, Sakura Express, later to be replaced by Savor Bakery.
Ross and Frank were music critics who trashed Ben at one point.