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.
I was about 16 and made a Slax CD to get around my schools locked down WinNT/XP installs. After school I ran Ubuntu on an '06 Acer laptop for a while but later switched to W7 for gaming. When W10 launched with ads in the start menu I moved to Debian and have been totally happy since then.
