That reminded me a bit of that time I was spending the summer at grandparent's and went to the gas station to buy a few things I needed, and saw a magazine special dedicated to a tv show that was really popular with girls at that time, including a dvd and 3d anaglyph glasses. Picked it too.
Cute early 20s girl in the counter: "ohhh, do you like this show?? :D" Me: "no, I'm just buying it for the 3D glasses for using them with Minecraft" girl: "oh okay :/"
me, almost a week later, playing Minecraft at 3 or 4 AM: "wait, was that flirty?"
My first one was Star Trek TNG: Advanced Holodeck Tutorial for Game Gear. I wasn't really a trekkie back then (had watched a few of the TOS movies with my dad and liked them but didn't really care much about Star Trek until around the 30th anniversary I think). I remember thinking the game's enterprise design was dumb and wanted the stylized one from the movies back (and Kirk and Spock and Scotty instead of these "random stand-ins" :P)
And I think my favorite one was a heavily modded Bridge Commander. I didn't really play much of the actual game (or "the campaign" as kids call it today) but spent probably around 100 hours playing custom scenarios, battles from the movies and shows.