Real talk, I have the Oregon Trail video game board game and my wife and I were playing it for the first time and she said "you start first so I know what to do" so I flipped the first card and immediately died of a rattlesnake bite leaving her to play on her own
I haven't really played the board game, as my wife and I usually get caught up in longer ones. But I do have childhood memories of killing many a brave group of pioneers with poor planning and too much bad meat.