For me, I started with RedHat 6.2, dual-booting it with a Windows 98 machine... then tried other distros (including one called Caldera) before going with Mandrake. After a while, I got side-tracked... and then started to work on trying to set up an older home machine as a server, and worked with DSL and Zenwalk before getting side-tracked again... then when I got an older laptop from my father-in-law, started using Ubuntu, especially when it just worked without getting too bogged down with eye candy. That was followed up with Linux Mint, which now shares space on my laptop with Windows 7, while another laptop has version 1 of Peppermint Linux (it works, so what the hey?) and serves as a file server and alarm clock. I have different distros burned onto flash drives, and hope to have more soon.
This is probably an indication that I am all over the map - so if you can find a pattern out of all of this, congratulations!