Windows (for many years) -> Ubuntu (for a year) -> Arch Linux (for half a year) -> Void Linux (literally 2 days) -> Artix Linux with runit (a month) -> Gentoo Linux (another month) -> Debian (finally, I don't plan on changing it).
Started on a Windows Vista machine, but I dual-booted Mint on it when it started to run slow.
The software broke or got corrupted, so I installed Lubuntu.
Lubuntu started to freeze, so I installed Mint again.
The hardware was really outdated at this point, so I got a new machine. Windows 8.1.
Got a different new computer with Windows 10. Started trying out lots of distros of VMs.
Switched out the drive and installed... OpenSUSE, I think?
Catastrophic system error during an update, left the system corrupted. I installed Debian.
Another system error (which may have been caused by me) led me to install FreeBSD.
FreeBSD was usable, but not super usable. I installed OpenSUSE Tumbleweed.
Catastrophic system error during an update, left the system corrupted. I installed Debian (again).
tldr: Windows Vista -> Mint -> Lubuntu -> Mint again -> Windows 8.1 (new computer) -> Windows 10 (new computer) -> OpenSUSE Leap -> Debian -> FreeBSD -> OpenSUSE Tumbleweed -> Debian again