I went from buying physical copies at local stores to going out of the loop for nearly a decade (for several reasons), to buying digital games on GOG. I arrived here in search of classic games and I stayed because of the offline installers.

Nintendo when I was 6 years old (rentals, I had the weekend to finish a game)

Super Nintendo whenever it came out and also Sega Genesis about a year or two after that (still rentals)

I got my hands on my first pc when I was 13 years old. A friend passed me a whole bunch of games on a floppy (my first real experience with having permanent game copies).

Then, a year later or so, I bought sharewares at brick & mortar stores (that's how I got Doom) and not long after that, full games (Ultima Underworld and Master of Orion were among my first purchases), also at brick & mortar stores.

Since I joined GOG, I pretty much only bought games here (bought a handful of games at DotEmu and Humble Store, but that's it).

I have bought games last year from:
Steam
EGS
UBISoft
Origin
gOg
Humble
Fanatical
itch.io
Battle.net
+ some direct from developers

Grew up buying games for my C64 then moved to PC. Hard copies from local EB Games or JB Hifi.
I did have steam for a while, but havent bought anything from them for about 4 years?. Pretty much bought most of my games from GOG, some from bundles (drm free games music etc), Humble, exploring stuff on itch right now...

When I was young I bought a few game for my DS and 3DS, when I found out about terraria I bought on GoG and that was my main platform for buying games as rare as that was.

Now I mostly buy on either GoG, Steam if it is a game that isn't on GoG and the occasional switch game.

I have 1 main problem where I hate spending money but that is more of a good thing then bad thing because now I have a good amount of money.

I started buying games in the beginning of the 90's. The first games I bought were Battle Isle, Populous 2 and PowerMonger for Amiga. In those days - living in a rural area - I bought a few games in a local store, but they had a very limited selection. So most games came through mail order. To save on shipping costs me and a few buddies who also had stopped pirating started to order together.

Later came DOS and then Windows games, by then I lived in the city with plenty of choices from dedicated stores (with 18+ sections with blacklisted games!) to malls, so mail order wasn't needed any more. Until I became obsessed with getting the (if original) English versions of games - I ordered a few from Amazon UK.
I pretty much stopped buying physical games, when online activation and Steam infestation became a thing. Only the odd magazine cover game now and then (those were mostly rid of any form of copy protection).

Nowadays I buy mainly on GOG, some stuff I have from Humble or itch.io. DRM-free is the requirement, and yes, I do see the need to use a proprietary client to download the game in the first place as DRM. If GOG ever stopped offering the offline installers, or forced us to use Galaxy to get them I'll be gone here.

I've been doing this...well, forever.

Arcades were my first jolt of games. Games like Pac-Man, Ms. Pac-Man, Galaga, Punch-Out (arcade version), Mario Bros. - yeah, played the heck out of them.

I began gaming on home systems with an Atari 7800. Eventually, got a NES. Then a Genesis. Then...in 1995, my first Windows PC.

Even back then - still was going to arcades, for certain games...like the Street Fighters, Mortal Kombats, Primal Rage, Tekkens, etc etc...before they hit home systems with a port.

Since Windows, really haven't done much with consoles.

I did get an old-school Playstation, way back in the day - but that was my last console. Wow....FF7, Silent Hill 1, Chrono Cross - my final real console generation. Well, other than buying a Playtation Classic recently, a year or so ago or whatever, when it was $20...for some Playstation Classics that I was missing (like Tekken 3 and MGS).

I've been buying PC games...wherever. I go where the games I want to go are.

I'm not fond of DRM - but, you know, I gotta buy what I want to play, DRM'd or not...unfortunately. [shrug]

I think I really began caving with DRM on phone-home games with online-activation with Mass Effect 1.

Around when Steam got popular, retail...kinda died for me. Sure, I still bought some games from retail - but when Steam began running crazy deals, back in its golden days when Flash Deals and No Refunds were a thing - a lot of it came from there.

Most of my purchases of late, they likely have been for games utilizing Steam and/or 3rd party places with those keys - i.e. Humble, Amazon Digital Video Games, Retail boxes that had a game requiring Steam, Fanatical, NewEgg digital downloads/codes, etc etc.

Can't really recall the last time I say a bought a game from same Direct2Drive, Gamersgate, or some of the other PC gaming digital shops. Probably been a while. Heck, does D2D even exist anymore?

Sure, I do buy stuff from GOG, UPLAY, Origin, Microsoft Windows Store, Epic Game Store, etc etc. when there's something good on sale and/or something that I really want - but I think most of my game purchases now are from Bundle Sites like Fanatical and Humble. And most purchases from bundle sites like those, they utilize Steam.

I bought from various physical stores in my area when I was younger. The last physical copy I bought was most of seven years ago, and that might well be the final one.

With regard to digital download PC games, I've spent a fair bit of money (for me; I'm sure it's dwarfed by the amount spent by many who've been here a much shorter time) on GOG over the course of the last several years. I've occasionally bought stuff on Humble, but they seem to have mostly ceded the DRM-free market to GOG (which is a bit of a shame, as they are the only remaining major player serving that niche that doesn't have even an optional client application). I've spent money on one game on itch (whose lack of any consolidated download library keeps me from spending more there).

It is a bit hard to remember but if memory serves me correct my first truly bought game from my earnings as a paper boy must have been warcraft 2... or red alert ..... Silly but i also remember that one of the first pieces of clothing i bought was this longsleeve from Paul Elstak... with the bear.... wanna play i belief was the script

oh and my last physical purchase was either Mass Effect 3 or Rome II ;-)

My first physical purchase was "The Beauty and the Beast" from Disney Software and the last "The Elder Scrolls Anthology". Nowadays i bought digital all. I don´t mind to buy several times the same game, for "back-up". I bought keys for steam for cents, free stuff on epic (one day i will buy something) and the most purchases on gog.

I've probably spent more money on GOG games overall, since they don't have nearly as much garbage/shovelware as Steam, and they're DRM-free. I have 741 games, assuming that about a dozen or more were free, still probable that I spent more money on those than Steam, even though I own 1312 games on Steam.
Especially since I discovered www.isthereanydealcom , I bought a whole lot of bundles on sites like Fanatical, Humble, Greenmangaming etc. for like 1-5 € each, for like 4-10 games... so on average I pay more for single GOG games. And pretty much all games I own on Uplay, Origin or battle.net were store-bought, or they're also on Steam and require the respective launcher.
And I have 57 games in my Epic games library, which of course I don't really own because DRM, but I also paid for none of them, they're all monthly redeems (or weekly in the holiday season). (Also, the number is not including Fortnite or any other F2P titles on there)

Interesting reads folks, thanks for sharing. :)

Some of you have mentioned the first computer games you ever played.
I guess mine would have been at game arcades as a kid some 40 to 50+ years ago ... Space Invaders no doubt ... though maybe it was something like Pong Tennis etc first.
Playing Pinball at the local Fish & Chip shop was undoubtedly my first game experience, other than board, card or physical games, but that wasn't really a computer game ... being fully mechanical and electrical from what I recall.

I bought some games on Steam, back when I wasn't aware of the whole DRM-free issue: the first was Portal, then Half-Life (no choice but to buy there anyway), followed by their respective sequels (again, no choice) and a few others.
I bought a bunch of games on GamersGate, too, because of the inviting prices; but then, after I discovered GOG, I have only bought here (never on Epic, Ubisoft or other places).
I have never bought physical copies of PC games, save for an old CD-ROM of Dragon's Lair and a budget release of Starcraft (which Blizzard gave away for free shortly after...)
Before this, I cannot say I've ever spent my money on computer games - I mean, I had a good number of C64 games (and even Atari 2600 games beforehand), but they were all gifts from parents or friends, or pirated copies. As for the Amiga, they were all pirated copies (hey, I was only a kid, I know it was not the right thing to do...)
Finally, about coin-ops: I think I've played no more than two or three times with my money. My experience with arcade machines is extremely limited anyway; the time I played them the most was in Rimini in the early 80s, on a budget provided by my aunt and grandmother (mainly a racing game, I think Pole Position, Pac-Man once, which I found extremely difficult, bowling, and pinball).

My local electronics store if I buy PS4 games (lately Amazon, because most stores are closed due to the pandemic) and gog for PC games, rarely Steam (I think Monster Prom (1) was my last purchase on Steam). It's been years since I bought on Origin or UPlay.