I have been rereading Dave Barry's Dave Barry In Cyberspace (published in 1996), which has held up about as well as Neal Stephenson's In The Beginning Was The Command Line (1999).

On the software you'll need for your personal computer:

First off, you need an operating system, which is the "Godfather" program that operates behind the scenes, telling all the other programs what to do, making sure they cooperate, and if necessary leaving the heads of horses in their beds. The most popular operating system in world history as of 10:30 A.M. today is Windows 95^☺, but there are many other options, including Windows 3.1^☺, Windows 3.11^☺, Windows 3.111^☺, Windows for Workgroups^☺, Windows for Groups That Mainly Just Screw Around^☺, Windows for Repeat Offenders^☺, Lo-Fat Windows^☺, and The Artist Formerly Known as Windows^☺. There is also the old "MS-DOS" operating system, which is actually written on parchment and is rarely used on computers manufactured after the French and Indian War. And there is "OS/2," which was developed at enormous expense by IBM and marketed as a Windows alternative, and which has won a loyal following of thousands of people, an estimated three of whom do not work for IBM. And of course there is the Apple operating system, or "Apple operating system," for your hippie beatnik weirdo loner narcotics-ingesting communistic types of Apple-owning individuals who are frankly too wussy to handle the challenge of hand-to-hand combat with computer systems specifically designed to thwart them.

On the internet:

... I had managed to send this hideously embarrassing message to everybody in the world except the person who was supposed to read it.

Yes, thanks to the awesome communications capabilities of the Internet, I was able to make an intergalactic fool of myself, and there's no reason why you can't do the same.

Prefiguring Clay Shirky's cognitive surplus arguments:

So go ahead! Get on the Web! In my opinion, it's WAY more fun than television, and what harm can it do?

OK, it can kill brain cells by the billions. But you don't need brain cells. You have a computer.

The origin of Bill Gates's wealth: "versions."

How much should your new computer cost? "About $350 less than you will actually pay."

Also, I am gonna avoid G7e rage and not quote the entire section, but check out the Comdex chapter for Barry's thoughts on the limited range of stories and game mechanics available in games written by and for men in 1996, and his speculation on what more diversity would look like.

The fiction short story that appears in two parts at the end of the book causes disproportionate feels in me, because it's about falling in love with a stranger via America OnLine chat, and I read it around the same time I fell in love with a guy I met on Usenet, via a Dave Barry fan group. Oh dear I just looked him up and he has a freaking beard. I don't know why that detail gets to me, but I was not prepared for that. At this moment I am under a blanket on my couch in New York City with midmorning light bouncing off brick and fire escapes outside, but I am also in hand-me-down tee shirt and shorts in front of a 486, easily remembering how to turn the audible modem volume all the way down so Mom and Dad don't hear me dialing in, the mousepad the only clear area on my dad's desk that's cluttered with printouts and Post-Its and boxes of 5-and-a-quarter floppies, navigating to HoTMaiL, California night outside the blinds. And now I'm remembering all those other local maxima and minima of my teenage life, and how intense things felt. He sent me a photo and I printed it out in black and white and took it into my AP US History test. That printout is probably still in a box somewhere. He dumped me, and we never met, and I wonder whether either of us still has a copy of that email.

And now the only Dave Barry book I own is Dave Barry in Cyberspace. It's still funny and it still has a barb in it. I am genuinely curious whether people ten years younger than me would enjoy it, since clearly part of what I'm getting out of it is nostalgia. And now I'm thinking about setting a reminder to myself to read current tech humor by Rose Ames and James Mickens in 2035.