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I probably found it not that long after it started in 2008 when I trying to find a solution to my physical copy of Feeble Files not working on Vista. It was January 2009, when my next student loan came through, that I joined and bought the game.
In all honesty i think it was a search on GOG for a game(s)....
I backed the "Wasteland 2" Kickstarter. While waiting for W2 to be completed, they gave everyone a free copy of the relaunched "Wasteland" game on Steam or GOG. I didn't like Steam much, so I chose GOG.
A (rather) famous Youtuber named PaulSoaresJr mentioned GOG in a tweet that they had released Ultima IV for free. I had no idea what it was signed up, decided I didn't really like it, and proceeded to ignore this site until the PWYW Divine Divinity sale in 2012 (save for the Fallout giveaway).
I was doing some spring cleaning deep in my wardrobe and you know the rest. The worst of it is that that hack C.S. Lewis stole my idea and made a ton of money off my experiences...
I found out about GOG in 2010 when I was still a filthy pirate, finding a version of Blood that worked on my system. I eventually registered an account in October of that year, and purchased Kingpin: The Life of Crime because I couldn't get a version that seemed to work right on my system. Ever since then, I have been a dedicated member of this site and I have no intention of abandoning it anytime soon.
If I recall correctly, I first heard of GOG.com shortly after it opened its doors from one of this guy's blog posts.

Edit:
And, here is the post. Mostly looked it up to sate my own curiosity, but figured I would include it here in case anyone wanted to see the post itself.
Post edited January 10, 2014 by Krypsyn
In the back of a dirty magazine, next to the Russian mail-order brides section. My wife has since left me but GoG is still here.
Post edited January 10, 2014 by scampywiak
I was on an abandonware site, very likely looking for one of Sierra's "Quest" series games...I'd played them back in the 80s & 90s. I don't remember for certain, but it was one of two things. It was either a "This game has been removed because it is now available on GOG" message, or I saw some kind of banner ad. I don't remember which because I've seen both on many abandonware sites. I'd also say with maybe 80% certainty it was one of the old "Home of the Underdogs" sites (as there were a number of those)...20% chance it was Abandonia itself.

Its been like 4 years or so, I'm lucky I remember this much.
I think it said to redeem my GOG key on a copy of the Witcher. So I went ahead and did, thought it was neat, and ignored it for a few months, until I remember how awful I was at emulating Blood.
I honestly can't remember exactly. I mean I know I was looking for a source for older titles. However, I'm not 100% sure what lead me to join GOG. I know it was around the time of the Fallout 1 giveaway but for some reason I think I was a member before it became free. Not a long time before but maybe about a week before it became free. I really wish I could remember exactly. I'm happy though I joined as I have purchased quite a few titles since that time and am always pleased with the titles I purchase from here. It has the ones I want in a way I want. I do admit I would like to see more games from some other publishers and see more releases but I'm pleased with all that is available on here.
Someone at the Humble Bundle page told me about this.
Typed Google in wrong
Some game news site or other, possibly Kotaku, posted a link to Wing Commander: Privateer the day of its' release. Insta-signup-and-buy.
A few years ago I bought a Games magazine with a full version of 2 Worlds. Unfortunately, this version still wanted to "phone home" to be activated. I googled a little about this matter and finally found gog with the drm-free version.