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Good luck! Hopefully you have more patience than I do. I got Croconaw to level 24 and even then its water guns weren't really even putting a dent in Houndoom.
I think it just works a little slower than normal, I've evolved a Crobat and Snorlax fine. There's a groomer in Goldenrod who should be able to help boost the friendship up a little bit
Hey, really weird question, but is there any unique dialogue or a cutscene if you beat Shane during the first fight? I was originally gonna grind it myself to see if I could manage but his team is still super tough even with my starter being the same level as his lead and I don't think have the...