Well two year old Thread, it looks like Half Life 2: Deathmatch was my first purchase.
The Orange Box was the initial thing that made me create an account.
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My first registered game on Steam is The Orange Box which I bought from a store. But my first game bought from Steam itself is Mass Effect.
You can check your Steam transaction history by clicking on [INSERTUSERNAME]'s account and then account details. It should show every transaction on Steam you've ever had. Hope it helps if you don't remember.
The Orange box. One of the best Christmas gifts I've ever been given.
EDIT: that was just the CD key you get with the retail copy though. Got that in 2008 for XMAS. In 2010 I got the valve complete pack (which had every valve game except for portal 2, CSGO, and DOTA2). I also got Mass Effect 1+2 and super meat boy on steam during that XMAS. It was pretty sweet!
Super Meat Boy for $7.49 which I thought was a great discount in 2011. I've barely put an hour into that game :(
My third purchase was Borderlands GOTY and put 84 hours into it on a laptop that really had no business running it, so those early purchases evened out.
When Steam launched for Mac it came with Portal for free. First game that I purchased for cash would have been the Orange Box which is why I have these - http://wiki.teamfortress.com/wiki/Earbuds
The first game I bought using steam was F.E.A.R.. I remembered enjoying the demo when I played it a few years prior, and I wanted a game that was actually scary (It did have its moments, but it turned out to be nothing special in that regard). I think I didn't wait for a sale either, which was pretty dumb.
I believe I registered my HL:Blue Shift key during beta, I think it bugged or something as I got every single retail HL1 product available at the time (and still have them).
I purchased HL2 on release like most people, was probably that.
So the first set of game(s) I actually had on Steam was the Half-Life Platinum Edition. It had HL, CS, TF as well as Opposing Force and Blue Shift. When I entered one of the keys it knew I had the rest. I think it may have thought you had the same set.
Rag Doll Kung Fu. First non-Valve game released on Steam in 2005. Also the first "Indie" game I purchased.
The first thing I ever registered on Steam was the Half-Life Platntium pack, which if I recall correctly, was Half-Life, Opposing Forces, Blue Shift and Counter Strike.
The first game I actually bought however was Portal.
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