PokéBase - Pokémon Q&A
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And more importatnly, in challenge mode, do I have to start over again? As in I get a starter, play thru the story again, kick team plasma's ass and become champion or is it just me spawning in the house and playing thru the game again but with the mons I had in whatever the difficulty is of when you first play the game?

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You unlock Challenge Mode by beating the Champion in Black 2 specifically. In White 2, you get the Easy Mode key. If you play White 2, you have to communicate with a Black 2 game to get the key. If you decide to play challenge mode, your previous save data is deleted. I know, it is really dumb.

Hope I could help,

Source: experience

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Am I glad I was playing white 2 and not black 2. Here I thought trade evolutions are stupid. Thanks