First system was a Game Boy with Zelda: Link's Awakening.
Shortly after that I lost my first tooth and my mom got me a copy of Yoshi for NES (I had wanted it for GB). She felt bad and later got my brothers and I an NES. We went through three of those

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I wanted an SNES incredibly badly (played it all the time at my cousins' and daycare) but my somehow knew about consoles and waited and bought us an N64 about a year after launch.
My brother's both had GBCs and I played theirs all of the time and I ended up getting one for Christmas.
I broke my arm in junior high and for some reason my mom bought me a GBA which had come out about 2 weeks earlier. I got Golden Sun, THPS2, and Advance Wars with it

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My brother and I bought a Gamecube shortly after launch.
The next year we were at a flea market and we bought a PS1, the first non-Nintendo system in our family.
We liked PS1 so much we borrowed one of my brother's friend's extra PS2s. After that went bad I bought one of my own.
I didn't buy any consoles for a few years until I started getting into gaming again my Junior year of college. After drunkenly winning $100 I bought a Dreamcast. I got a Wii that Christmas, replaced my phat PS2 with a slim, bought my brother's DS along with an SP, and also bought a Genesis (which I later had to sell along with the Dreamcast). To congratulate myself for getting a job after college I bought a Japanese Sega Saturn.
"There are two ways to get enough. One way is to continue to accumulate more and more. The other is to desire less." G.K. Chesterton
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