What was your first operating system?

[Astolfo2001]

and some Pokemon Trading card game that was on the PC back then.

Did you mean that one infamous tutorial of the Pokemon TCG called Pokemon Play It?
https://www.youtube.com/watch?v=1ZKfLTRZDjM
I say the game's much more infamous due to its poorly-rendered CGI intro that looks like it came from the same animators who did the final, released version of Foodfight than the actual gameplay though:
https://www.youtube.com/watch?v=Cpf25GfbjpM