My proudest moment in gaming that I can think of at this time, occurred recently. It was me re-playing "Lunar: Silver Story Complete" for the PS1. More specifically how I had beat the final boss and completed the game.
I had been pounding on the main boss for over 45mins. In the end I had used all my sources of healing, all my MP was drained, all characters were dead except for 1 which was my healer and was out of MP and was 1 hit away from death. It was my lat turn, I struck with this ultra weak character and it happened to be just enough to finish off the final boss. I cannot express how elated I was after that. Knowing that I was 1 turn away from defeat and manged to squeak by with a victory. That is my proudest moment of gaming in recent memory.
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