I'm probably on the younger side of Lemmy, my first OS was Windows 98, but the first one I truly remember using is XP.

When I really started getting into computers, our family PC was running Vista, and the first nerdy thing I remember doing was trying to "downgrade" that computer to XP. My parents were none too pleased when they saw that the PC wouldn't boot, thinking I had bricked it. It took me about a week to getting XP running properly, and that feeling of satisfaction is what started my love for tinkering with computers (I'm definitely a noob compared to the average Lemmy user, though).

Afterwards, I fell into the Apple fanboy pipeline and begged my parents for a MacBook. I was a huge Mac nerd, even saving up money as a teen for an iMac, until I started wanting to game more on PC, especially with friends on Steam. I then started dual-booting, initially XP but then Windows 7, and eventually I realized I was never booting into my Mac partition. I played around very occasionally with dual-booting Linux as well, Ubuntu and then Linux Mint, but this was more for computer nerd clout than a genuine need or interest for libre software, also the command line scared me and I still played too many games to main a Linux distro.

I then built a PC for gaming, and ran Windows 7 on it until around 2 years ago when I got really into FOSS and switched to EndeavourOS which is what I've been happily using ever since. I've always enjoyed tinkering on computers, but with EndeavourOS I feel like I'm less battling with my OS and more with my lack of skill/knowledge, which is much more rewarding to surmount, and makes me feel like my system is truly mine.