There was one time when I was a little kid. I was out shopping with my mom and there was a Pole Position there, so I asked her for some quarters so I could play. It wasn't my first time playing the game, but for some reason that day I was just fucking awful and kept crashing and burning right off the bat. Each game lasted me barely a minute and just like that my quarters were gone. I was mad and frustrated and determined to do better, so I went and found my mom and asked her for some more, feeling humiliated that I needed to get more money so soon. I stormed back to the machine and once again, sucked so damn badly that my quarters just evaporated. I returned to my mom, but this time I didn't ask her for more quarters, because I was too humiliated and ashamed at how fast I had manage to waste them all. Then she asked me if I had fun, since she could see I was agitated, and I cried a little bit in frustration.
That's the only time I ever actually cried over a game. There have been plenty of other times where games have made me frustrated and enraged, but that time was a unique combination of being very young, in the position of having to beg my mother for quarters, and then ending up wasting them switfly by playing really badly in a game where I knew I could do much better. Oh the SHAME!