There are two moments that I remember of feeling sad. One was when in a game of Colonial Conquest I was ready to invade Siberia (controlled by Russia) and had moved about 3 million troops there with 800 ships, invaded and lost 2.5 mil in one season and not get the territory. (I was playing as Japan). Not only that but my friend (who was controlling Russia) invaded Manchuria (where I staged my invasion from) and captured it. Spying on the territory I found that he had about 5 mil troops there. What a massacre. The war went on for another 15 years without anyone succeeding to progress enough to be considered a winner. Great game.
The other moment that comes perhaps a bit closer to crying (but not crying) was when I let myself lose a game (meaning I didn't quit when things were a lost cause) in Civilization II(or I I can't remember) and I got that small sequence with the tablet or something saying ".....will rise again". (or something. Excellent!
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