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I found GOG in a games magazine. They were talking about the three principals, about then, webs where you could buy games in digital versions: GOG, Steam and Origin.
From what I can remember, I was looking up Disciples 2, and saw that it could be purchased on gog.
I think it may have been a slashdot posting.

My first purchase was the Might and Magic 6-pack. Of the classic cRPG series, the one I hadn't experienced before was Might and Magic; I was more familiar with Ultima, Wizardry, and Bard's Tale at that point. I believe the site was still technically in beta when I bought it.

I remember the time when gog.com closed down as a publicity stunt.

I also remember the gender selection when registering, which had a lot of choices; I chose Jedi.
For the umpteenth time:

I don't remember quite exactly when I read about it the first time. Possibly sometime in 2009-2010, reading about some site selling older PC games. I wasn't fully sure if it is a legit site or a pirate site, but I figured maybe it is legit then and thought "neat". I didn't check the site then though, maybe i felt I already have quite enough old PC games as retail versions.

Then later came the news that CDPR will remove DRM from The Witcher (and TW2?), and I took great interest to those news because I recalled hearing good things about The Witcher game years before, and getting it without DRM sounded like a dream come true, almost too good to be true.

At that point I also learned they are selling the game(s) as digital downloads on that same GOG.com site I had heard about before, so I checked the site because being able to buy a downloadable version instead of a retail DVD sounded even better. First I thought there is some catch, but turned out there is not.

About GOG's marketing stunt in 2010 about closing down the site for three days... I don't recall ever hearing about that back then, but it is possible I saw some articles about GOG.com due to that stunt. Still I feel I really didn't learn about that marketing stunt until reading about it here on the GOG forums, older GOG users talking about it like some kind of war or army stories.

The first game(s) I bought from GOG.com as a kind of test how the purchasing system works for me: on June the 27th 2011, M.A.X. + M.A.X.2 bundle and the Castles 1+2 bundle. Apparently it took me three weeks or so after that before making my next GOG.com purchases.

The games I came to GOG.com for originally, The Witcher 1-2, I apparently didn't buy until August 19 (2011) when TW2 was on sale for $29.99. I bought also the first The Witcher game at that point, for the default price of $9.99 (not part of a sale), and a bunch of other games.
Post edited February 29, 2016 by timppu
I tripped over it. My place is a mess.
I was looking for a few old games and I ended up on a certain piracy site, and most of the best downloads were tagged with 'GOG'. I thought it was a release group at first, but eventually realized it was of a store. I opened an account here, started buying stuff and reading the forums, which really changed my perspective on piracy.

I've never pirated another game to this day, and I doubt I ever will again, so you could say GOG has been a good influence on me :)
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Aze93: So, how did you discover GOG and what was your first purchase?
1. First purchase Planescape: Torment =)

2. Discover GOG with the help free Duke Nukem 3D Atomic Edition 13 december 2012 (23:54 MSK).
http://www.gamespot.com/articles/duke-nukem-3d-free-on-gog/1100-6401475/

P.S.
Post edited February 29, 2016 by Casval_Deikun
In my case, it's been so long that I don't recall exactly where I read about it...one of the bigger gaming sites, possibly IGN. This was way back in the first couple of months of GOG in 2008.
I googled gog.com....
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Aze93: So, how did you discover GOG and what was your first purchase?
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Casval_Deikun: 1. First purchase Planescape: Torment =)
Yup, me too. In 2012, some guys on a french RPG website were going on (again!) about how Planescape was the best D&D videogame ever made, so I went looking for it on the net, hoping it was maybe available on some abandonware place. Google sent me to a place where they actually sold a legal copy of it, and also of cult games from my youth, like Master of Orion2. It was love at first sight
Hotline Miami called, they said nothing about killing a whole bunch of gangsters. But I did anyway.
A friend told me they were giving away Duke Nukem 3D for one day back in December 2012 so I joined. After that it has been a downhill of money spent and games played.
Probably straight from Abandonia or HotU...
I joined with the Fallout freebie. My first actual purchase was a lot later though, almost 9 months later I bought The Witcher and The Witcher 2 in the Xmas sales. Then I got the D&D Classic collection in april 2013, a year after I joined. The rest is history as my catalogue and backlog grow, but strangely my wishlist too...
I searched for a place to buy Heroes 3. First thing I bought, alongside Heroes 2.