In all honesty I've only played Pokemon stadium, and not the portion where you actually get to be the characters (but to anyone planning to play, use Scissor! He is unbeatlable!...Well, atleast he is when I use him). Oh, and I've also watched my friends curse at Hey You Pikachu with the dumb thing nodding all the while. Couldn't have been Satoshi's Pikachu, it's way smarter than that thing.....Augh! WAY off topic! Anyway, I have no clue if there is any evidence in the games, but supposedly Gary is still Ash's rival but he gives out hints and stuff. Yea for him, I'm done here....
WAIT WAIT!!!!!! I have real games evidence know, as sent to me by Keela She says that in Pokemon Yellow (? we think it's this one...) Gary calls to Ash, "Smell ya later!" Now that could be taken quite kinkily (is that even a word?) or it could just be a closing line. Either way, it's obvious he's planning to see Ash again ne? ^_~