gary confessing instead, since he's the more mature of the two, and ash being all child-like chiding himself that it's wrong, and that he cant feel that way. But I can see them gazing at the moonlight like that one episode, where they talk about their friendship and how far they have come once again. Gary trying to avoid the subject, but lightly brings it up again, while ash tries to dance around it, and then somehow, gary questions ash so much, that ash grows enrage, and storms off into the night leaving half of his pokeball behind...and then yada yadam
and then Gary stumbling into the night whilst getting lost, and just pondering his own thoughs, asking himself why, would he pressure ash to answer, and asking why ash would get so defensive and storm off, and as soon as he completes his thoughts, ash stumbles into him, growling at him while a mild blush streams across his face, cause the moment their eyes lock they both know. They both know their feelings for eachother.
I can only see one voice-ing their liking for the other, but I cant see both of them confessing, the only way I can see that as possible, is the way you said it in your last post. But I can see them for some odd reason, just locking gazes and knowing the other feelings the same, a unspoken understanding you know?
and then gary would give him his respected half of the pokeball, saying something philosophical like "Two halves of the same whole, eh? Without the other, it cant ever be complete or a whole, ashy-boy" and then ash would direct his gaze somewhere else, a shadow hiding his expression, uttering a a strong whisper of "Yeah...your right."
Definitely Gary confessing.
I actually believe he started being 'mean' to Ash because he had a crush on him. Boys that age usually make fun of the girls (or boys) they like.
So I believe Gary is now aware of his own feelings and he will be the first one to confess them.
Well... it's just hoping XD