I always see everyones most recent, but I never see anyones first.
I’m talking about YOUR first (the one YOU bought with your own money), not your parents.
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Starting out with the biggest bang I could’ve ever hoped for. Rayquaza the GOAT!!!
My memory sucks so I’ll just say a BW pack
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Cool Porygon😎 from TCA! had no idea what i was doing, just thought it was a cool card! simpler times.
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I already had about $20 saved up being in grade school when this came out , so when it did I traded in a couple of my GBA games plus added the mula I had as a kid and got this work of art of a game. It changed my world for Pokémon games.
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Fake Base Set booster pack from the Chinese convenience store in 1999. Every pack had the exact same cards that were 3/4 the width of real cards with purple backs. Even as a kid I knew I had been hosed 
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2017 evolutions booster pack. Pulled a reverse holos charizard AND a M charizard EX full art in the same pack
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I thought a complete but unsealed skyridge booster box was a good buy in college at $300.
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In May 2014 I got back into Pokemon cards after selling my childhood collection and being out for a few years. My first purchase was some cheap modern (at the time) packs, but right after that I bought a few cards I had always wanted as a kid but never was able to get. The first was a Latios delta species holo for $4 in near mint condition. I still have it in a toploader and probably should get it graded at some point just for the sentimental value, although I did end up buying a 10 of the same card down the line.
I also bought a Base Set Zapdos for $6.50 soon after that. I remember a friend of mine had this card and I always idolized it but thought I would never have it. I had been working a part-time job for awhile, and I had some money saved. Imagine my excitement when I realized a couple dollars would get me the card I had always dreamed of. This card was actually in very good condition and I graded it myself eventually and it got a PSA 9. I still have it to this day and I love it.
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Some of the first slabs I bought:
Those are both long gone.
Completed the entire PSA 10 JP expedition holos set.. most I paid was $200 CAD and that was for the zard. Nearly everything else was under $100, maybe mew was 100 on the nose though.
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I beleive it was this backpack that I wore to school all year. I actually loved the anime/merch more as a kid.
(No, Im not kidding)
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With my own money I remember that my very first card were purchased around 2018-2019 when I bought my Western Nintendo e-Reader … I remember that I bought a bunch of e-Cards. One of the e-Cards included was Umbreon from Sandstorm …
I created my eBay account in 2020 … However I was not active until 2022. I remember I won my very first auction that contained 4 PokePark cards … (All of that was purchased with my money)
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Interesting question. I’m sure the actual answer is probably something else, but the first purchase that I definitely did on my own and can also recall (since it also was my first own tweet lol) is this one:
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Some time not too longer ago a thread came up where we were talkin’ about the good old days, the days before I even used ebay and instead opted for amazon (oddly) or tcgplayer.
On amazon it all started with this. A craving. A sweet tooth if you will.
Then of course after I had opened some 5+ packs individually for almost $20 a pack I was like why am I not just opening a box?
I found out after diving into ebay at some later that year I found out that’s where all the deals were, and got many more booster boxes both pokemon and yugioh alike.
Can’t remember what the last time it was brought up about buying cards back in the day, but I remember sharing this particular one in that thread cause it was so funny. It made no sense. You could simply combine orders for penny cards. But then again no one cared about pokemon so 
All these cards were pack fresh, good times.
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I have no idea tbh. 
Usually my parents bought me and my little brother booster packs for our birthday; Christmas; Sint Nicholas; if we got good grades after a school semester; etc. etc. But which booster pack I bought myself, I’m not entirely sure. I do know that I sometimes used my allowance money to buy booster packs, but which one would be the first, I honestly can’t remember. If I had to guess, I’d say either an EX Sandstorm or EX Dragon booster pack.
EDIT: Actually, now I remember! The very first pack I bought myself was a Legendary Collection booster pack on a second-hand market. I still remember pulling two Slowpoke from the same pack, alongside a Reverse Foil Moltres. Since it was a secondhand market, and I had never seen this holofoil type before, AND the pack contained two of the same card, I initially thought I had bought a booster pack. I even traded my Moltres for an Ancient Mew later on (one of many bad trades on my part). 
I did buy the Moltres again a few years back, though. For nostalgia sake. 
Then just before I came back collecting Pokémon cards, I bought these three alongside my Yu-Gi-Oh order from TrollAndToad.com on Dec. 14th, 2014:
These were the only three gen 1 Pokémon I was missing in the collection of my youth, so I bought these to complete the first 151.
Apparently, I’ve bought two Seviper and a Klefki on Dec. 29th, 2014 (alongside Yu-Gi-Oh cards again). I guess I’ve started collecting Seviper before Pikachu, even though I can’t remember. 
Then on Jan. 8th, 2015 we had the first two Pikachu cards:
But it wasn’t until Sep. 13th, 2015 that I went all in, and decided to start collecting Pikachu. In that purchase, still alongside Yu-Gi-Oh cards and other random Pokémon cards, I basically had every Pikachu TnT had in stock for <50 USD in my cart.
And damn am I missing these kind of prices. 
Here just some examples of the many ordered Pikachu cards:
Greetz,
Quuador
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1st edition dark blastoise holo from tonsofcardsandstuff
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I can’t actually remember which set my first purchase as an adult was from, but it was just a loose booster pack from the toy store around the time my firstborn was two years old. I hadn’t had much exposure to the toy store as an adult before then. My oldest eBay purchase is a Mega Charizard EX though. I started off collecting Charizard cards, then pivoted to Base Set and Black Star Promos, and continued from there.
If you are wondering why there is a random Meowth, it’s because it has a Charizard’s shadow in the artwork
My oldest memories of Pokémon are pulling a base set Charizard from a booster but then getting duped into trading it at school for a base set Gyarados, that was a sad day lol. Maybe that the reason i started collecting Charizard’s 
Begging my mother for a loose Fossil or Team Rocket pack from Woolworth’s is another (which she did) 
and also playing with decks with my older brother, i still have the Thunderstorm (TCG) gift box, as well as the metal pikachu coin in my personal collection today.
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After a period focused on yu-gi-oh I bought in 2015 a semi-complete Italian unlimited base set (only the nidoking was missing) in good condition for about $40 on ebay. From there I started collecting Pokémon again.
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