I've used Windows since I can remember... at least since Windows 95, then probably early 2000's, added OSX into the mix. I currently use an old Mac Mini as my Plex machine, and the computer provided by my employer runs Windows.
My "journey" began around 2015 on an old Dell laptop that I set up to dual boot Windows and Linux. I tried 2 or 3 distros, one of which was probably Ubuntu, before settling on Mint. I remember having enough minor issues with Mint that I kept booting back to Windows, and eventually stopped booting to Mint at all.
Then one day, I have no clue what I was trying to do, but I was confident that I knew what I was doing, so I just went for it without pulling up the instructions. Welp, I ended up deleting my bootloader, or something like that, and now couldn't boot to any OS. I tried using my parents' Mac to create a bootable USB, but that wasn't working. I wound up buying and returning a random open box laptop from Best Buy just so I could create a functional bootable USB. I also found help from a very kind internet stranger who walked me through the process to fix my bootloader. They happened to only use Arch btw, so that's what we used to get my laptop fixed.
That whole drama really scared me away from fiddling with it for a while, then I just got busy and had no motivation. That laptop is collecting dust and still dual boots Windows (7?) and headless Arch. I'm thinking of fiddling around with Linux again, but most definitely need something more noobie friendly than Arch without a DE.