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Pokemon battling is largely about learning the Pokemon types, their resistances and weaknesses. While overlevelling an Oshawott might let you beat the gym eventually, that takes a lot of time.

Choosing Oshawott means you'll fight a grass-type user at the first gym. However choosing Oshawott also means someone in the Dreamyard offers you a Pansear to cover your weakness. Train this Pansear up a bit, this fire-type should help you beat the gym without much trouble.

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Q: How do you beat the first gym with OSHAWOTT?
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