I firmly believe Gary should be the rival in every Pokemon game. No, I don't care if he's 45 by the time Diamond and Pearl or whatever is out. He should also continue to be a total dick like he was from day 1. He was 10 years old driving around a convertible and had bitches at his beck and call. This should continue. Whenever you enter a cave and come out with all your Pokemon are at 3 hit points? Gary appears. Get through Team Rocket HQ, out of any healing items with your best team reduced to rubble? Gary rolls up in his Mercedes. When you finally attain all the badges you need, with your favorite Pokmon battered and beaten? Yeah, Gary. All your Pokmon are knocked out and you're 5 tiles away from the Pokemon Center -- Guess who just blocked the entrance way and says he challenges you to a fight? Fuck yeah, Gary Oak
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"I could care less" means you care right now. The proper phrase is "I couldn't care less."