I’ll go first, I took my mom’s college textbooks which came with discs for a couple distros and failed to install RHEL before managing to get Fedora Core 4 working. The first desktop environment I used was KDE and despite trying out a few others over the years I always come back to plasma. Due to being like 12, I wanted to run my games on it, and man wine was not nearly as easy to use (or as good) as it is nowadays. So I switched back to windows until around 2015 or so when I spent the next few years trying to replace windows as much as I could. Once valve released proton, I switched fully and have t looked back, unless my still there windows partition tries to take over my computer when I restart it at least.
All I remember about my first time is being tricked into using Slackware. They told me it was the easiest distro. And this was in like 94 or 95; just a year or two after the damn thing came out.
Slackware was mine too - all it took was a box of floppy disks and tens of hours of downloading and installing! It was great though, something so different. But it was just a toy, and I went back to DOS/Windows on PC - mainly for the games and hardware support (Voodoo!)
A year or so later I spent a lot of time playing with Solaris and VAX/VMS at University and really developed a love for the command-line and UNIX environment. It was that which led me to my first job (with HP-UX) and my second (Debian/Yellow Dog). From then on I used it at home a lot more. Now I use Windows for games/gamedev, and Ubuntu for everything else (desktop, laptop, servers).
But it’s amazing how far things have come in some respects, but how some things have regressed over those 20 years - window managers/themes never reached the heights I envisioned in the Enlightenment hay day, session management/restoration/remoting seems to have been eroded away, virtual desktops/window management/tiling regressed and became fractured, the wonder of Compiz didn’t really move things in an interesting way, and I felt sure Quicksilver (for MacOS) was the future of launcher, but it’s not really been taken up - though the Expose feature is an excellent essential part of Gnome now (Activities)!
In some ways I think Linux has lost that “wow factor” that we used to have with all those cool features - but it is much more rock-solid and professional now! I use it more now than I ever have.