My first Linux experience was in 1998 (via telnet into my university's server to read my email with PINE). I've run Linux on my own machines off and on since 1999 and exclusively since 2006.
My first distro was Slackware, which I quickly broke. I then went back to Windows 95. After that, my friend helped me install Debian, which I used until I replaced that machine. I found Debian too difficult to install on my own, so I put Red Hat on my newer machine. At that time,
yum didn't exist, and Red Hat only offered updates if I logged in to X as root, which I rarely did. So, it quickly became outdated, and OpenOffice 1.1 couldn't handle right-to-left text, which I needed for one of my university classes. So, I started using my Windows XP laptop most of the time. I couldn't install Linux on the laptop because the NTFS tools of the era couldn't resize my partition.
After a couple of years, I decided to switch my Red Hat box to something more modern. I wanted to move away from the RPM package format, so I tried installing Debian again and once again found it too complicated to get all the features I needed. Then, I read about an up and coming Debian-based distro called Ubuntu that had just released their latest version. So, I installed 6.06 (Dapper Drake) and have used Ubuntu exclusively as my main OS all my machines since that time. I only boot into Windows a few times a year. I've tried a few other distros' live CDs, but so far have always decided that the benefits of those distros aren't significant enough for me to switch over.
For the first many years, I used the command line most of the time, as early Linux GUIs weren't up to many basic tasks. These days, the GUI tools have made leaps and bounds and are quite usable. Nevertheless, I often prefer the command line for many tasks. I'm much more likely to use
vim than Gedit. But, I quite appreciate GUI tools for a number of tasks--perhaps most tasks these days.