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 running LiteStep on Windows at the time, but wanted something more OSX like, ended up coming across Mandrake/Mandriva. Which led me to Slackware, which at the time was considered the ‘IUseArchBTW’ version of Linux.
Since then I’ve tried just about everything, the only real constant has been Debian. Every server I spin up is Debian based and has been since the early 00s.