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I have a level 29 Riolu, I believe he is on the verge of evolving. If I train him in Iron Island, cave like, will it evolve from happiness in the day time even if its dark like the night?

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Straight from Serebii


To evolve Pokémon via happiness, you must reach 220 it by doing the above efforts, once that is done, you can evolve your Pokémon by making it raise a level either through battle or a Rare Candy. Below are all the Pokémon that evolve through Happiness and what they evolve into


So make sure that Riolu has reached 220 to evolve.So the answer to your question is simply
Becuase Even if your In a Cave Its Still Day Time ;)
Hope I Helped WINK
Here is the Source to ensure you my answer is correct it says Riolu Evolves In the Day time I love Weird things ¯(°_o)/¯

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you like WINKing....
lol yes ;)