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Final Fantasy 6 - Negotiating With Gestahl
Time for a trip to the nostalgic past. Final Fantasy 6 features on doozy of an awkward dinner when the heroes are invited to have dinner with Gestahl, the evil Emperor that's been the big bad villain up to this point in the story. Being that he's still a problem for everyone involved, the scene plays out with dialogue trees, forcing you to follow the proper etiquette while in the evil Emperor's presense.
There's no way to fail the scene, but the added layer of etiquette earns this dinner a place on the most awkward dining scenes in gaming history. Also, the evil clown Kefka is locked up in a prison cell nearby - and, duh, it's all a lie. Emperor Gestahl turns on the good guys pretty quickly after all this eating and politeness.