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Me to a young man who read the McLuhan piece at Medium (which is trending well, btw) and is interested in the effects of social media

Given your interest in the effects of social media, McLuhan is probably right up your alley. VERY hard read. I slogged through Understanding Medium, then read a biography of him. I'd recommend doing that in reverse if this is an area you want to explore.

An easier entrance into this area would be Neil Postman's Amusing Ourselves to Death. It's short and fun (as far as this kind of reading goes).

You might also try Walter Ong, a Jesuit and McLuhan disciple. He's easier to read . . . but not much.

There's also Lewis Mumford, but I haven't spent much time on him.

McLuhan, btw, was a huge Chesterton fan, Catholic convert, and daily communicant. He also lacked propriety at times. While on a city bus with a friend, he saw a Coke advertisement with a pretty young woman drinking from a straw. He said, "Coke sucker." His friend replied, "Marshall, lower your voice."