Well, I've played X-Wing and Descent ever since they made computers with CD-ROM drives.
I'm not sure how I obtained a copy, but I got FS1+ST mostly because of the "Descent" name. I found it was an excellent game, so I beat it a few times and forgot about it. Some time later ('02-'04?) I learned that there was a Freespace2! I decided I had to have it so I eBayed it for a song. Beat that a few times and forgot about it.
Around '07, I stumbled upon Shadows of Lylat and Fate of the Galaxy and started following. A little while after that, I found out that they were built on a super upgraded FS2 engine, so I downloaded it, played through the main campaign, and forgot about it.
Then I remembered about it, upgraded late to 3.6.10, and just beat it again a few months ago. After that I decided to play a mod for the first time ever. It happened to be Blue Planet. That made me decide that I wanted to be a part of the whole community, which is why it seems like I've only recently arrived on the forum at large.
P.S. I have the FS1 and FS2 CDs still, I've gone through about 5 joysticks all together (now I'm using a Wingman Force 3D), and have between one and three demo discs.