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May 1, 2020
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Complicated question, but my first brand new digital purchase (aka a game I did not already own physically) was Banner Saga 2.
 
May 2, 2020
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Planescape: Torment - I wanted to try it because everyone said how good it was, but it took ages getting it to run without crashing and even when it did run the graphics were too glitchy to be playable. Very sad.
 
Nov 15, 2020
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My first game on GOG was Moto Racer 2. It's an arcade bike racing classic from 1998 that I have very fond memories of as a teenager playing. Two decades later, I had the urge to play it again but figured it was foolhardy as games that old seldom run on modern machines and operating systems. That's when I found out about GoG and saw they had MR2 so I decided why not. Much to my delight, it was well-optimised to run without a hitch and I've been playing it often whenever I have a short burst of free time to game.
 
Dec 10, 2020
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My first purchase was Raptor: Call of the Shadows

Bought it as I loved playing it back when it was one of the few games with native Gravis UItrasound support.
 
Dec 10, 2020
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My first game was Beneath a Steel Sky. Since it was free, I don't know if it counts. My first real purchase (my second gog game) was Shogo: Mobile Armor Division.
 
Dec 10, 2020
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My first purchase on GOG was Strong Bad's Cool Game for Attractive People, because it sounded like it's a game for me. And this is true, I'm not trying to be cute. That's just how I am.
 
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