1)I made a couple on the sims, got the wife pregnant, made the husband become a womanizer and had him go on dates whilst the wife was home with the baby. I had him bring his dates home and sleep with the date in the couples bed with the wife watching. Then make the wife and the date fight. Rinse, repeat. Had the husband knock up a few of his dates, and then made him propose to one if his dates, which she rejected, and he ended up dying of embarrassment, leaving behind 3 women as single mothers. Then had two of the mothers start dating.
It made an interesting family tree.
2)In roller coaster tycoon 3 I would put one guy on an island he couldnt get off of with like 100 lemonade stands that had free lemonade and one toilet that cost $500 to use.
3)In GTA V I chased a woman 30 minutes from downtown to Mount Chiliad because I wanted to see if/when she would stop running. Kind of a wild card ending, she ended up being mauled by a mountain lion.