oh, everything that @praxeology said, plus:

The Boy Kings - Katharine Losse
@npseaver's ethnographic work on recommender systems
The front matter of https://sarabander.github.io/sicp/ might be interesting through a kinda critical / historical lens
Ullman's "The Bug" might also be fun (it's a novel, but a very well-observed one, and i bet it'd be very generative of interesting discussion)