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.
Ubuntu when I was 14, although I needed a lot of help from someone who was already familiar with the system. because I didn’t have yet much of an idea how things were relating to each other and why some things weren’t just as with windows. Didn’t also really use it properly and switched back to Windows after a few months. Instead of an opportunity to explore my way of using the system anew I just saw hurdles of doing things just like I did with Windows.