As an editor to OutLines (the OSU Pride Center newsletter) and assistant editor to Teaching with Writing this year, I’ve thought a bit about typefaces more so than in the past. I remember being young and enthusiastic back in 1990 with my new Macintosh Plus and playing non-stop with fonts. And then seeing the same thing in my middle school students a few years ago when they’d work at the computer. Now, I’m a bit more reserved, and understand a bit more.
I forgot where I got this link from (it’s been sitting as a tab in my browser for a few weeks), but Michael Bierut offers Thirteen Ways of Looking at Typeface, which I think is pretty interesting.