PokéBase - Pokémon Q&A
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So, I locked a Pokemon in with Mean Look, then used Hypnosis to put the Pokemon to sleep. After that, whenever I use Nightmare, all it does is wake up the opposing Pokemon. Can someone please explain how this move works?

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nightmare saps 1/4 of the affected target as long as its a sleep and is cured when it wakes up you just might be having bad luck

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Nightmare only works when a Foe is Asleep. While the Foe is Asleep, Nightmare take away 1/4 of the Pokemon's health. It can only be used 1 time per each Pokemon. The best way to use it is with Darkrai's signature move Dark Void and it's Ability, Bad Dreams

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