The first videogame I ever really played was Red Baron. I had the Windows95 version and it was one of the only real games we had at the time.
Being quite young, I didn't fully understand the concepts, much less the design, but it was fun to fly around and the aerial battles were, for a game of its time, pretty thrilling. I always loved flying tri-planes.
My father taught me just enough about the menu to get me into a game, and I picked up a little bit more on my own over time. The campaigns were great, but there was one part of the game I could never get the hang of.
Oh, the dreaded "Realism" menu.