I took the first real steps (after the "Tandy 3000/dot matrix printer" disaster of much earlier, with a Packard-Bell Pentium 60mhz running Windows 3.11. That computer lasted for 5 years, and held up well against Pentium 133 and 166 computers and Windows 95
What roped me in was Doom, which we would laughingly try to play over a 14.4 modem connection. The friend who first showed me Doom II (on a '386SX) also got me addicted to Bulletin Boards, with all those door games like the ever famous Legend of the Red Dragon, or that one game I can't remember the name of, where you and your spaceship trade with and conquer planets, competing against others doing the same. Trade Wars? I can't remember.
The ANSI art, the RipScript, the eternal quest to free up more conventional memory without crashing the computer, and trying newer and different AT strings for one's modem. The days when DOS was king, and a 1.44 megabyte floppy was a lot of portable storage. "Multimedia" and the CD-ROM drive were new things (and had to be hooked up through one's sound card). All those PWads and IWads for Doom. YakWorld, I remember you well. The days when you set a bunch of zipped files for download via Z-Modem overnight, while you went to bed after having conquered three new worlds for your interstellar empire, chatted with friends, and posted on forums at your favorite BBS hangout.
Those were the days.