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.
Can’t remember why I looked into it but my very first experience was using Ubuntu Hardy Heron (8.04.4) on VirtualBox. At some point I also used Wubi to install either that one or one or two versions later on a desktop PC. Honestly I didn’t really “get it”, it was difficult to do anything (tar.gz files utterly defeated me), I really didn’t understand the concept of the apt package manager. I was curious but ultimately didn’t really know why anyone would bother using it.
A few years later I installed one of the versions of Ubuntu when they moved to the Unity DE (again on Virtualbox). I remember really liking it (only later found out how controversial it was) but yet again didn’t really understand why I would want to use it instead of Windows.
It wasn’t until around maybe 2018 or 2019 that I installed Linux Mint on a spare SSD in my computer and actually began using it. However yet again I still didn’t have a reason to use it - that was until I got involved with an open source project and trying to set up a dev environment on Windows completely melted my melon. The instructions to get the dev environment going on Linux looked so much easier, and it was. I’ve barely looked back since.