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Re:Lost something? Search through 91.7M files from the 80s, ... by yCombLinks on Tuesday October 18, 2022 @08:15PM (#33255820)
My favorite game matching that description is lucasarts "The Dig"
Re:Lost something? Search through 91.7M files from the 80s, ... by ailun on Tuesday October 18, 2022 @10:33PM (#33256802)
This was my first thought as well! I was weirdly obsessed with that game. It crashed all the time, so that part fits. I originally had the demo on CD, I think it came with X-Wing vs Tie Fighter or one of those other Lucasarts games.
Re:Lost something? Search through 91.7M files from the 80s, ... by nebula8804 on Wednesday October 19, 2022 @02:32AM (#33258477)
I added more info here after others helped get more out of my head

[1]:https://news.ycombinator.com/item?id=33258294

The game was definitely a Win32 application so it wouldn't have the style of "The Dig"