-shrug- If you've read books or even applied to real life, people fall in love at different ages. Some get engaged even before theyr'e 8. So.. XD It really depends on the individual.
So, anyway.. I'm not much of a Pok?shipper, and even if I was, I like it one-sided. Personally, I think the times Ash does get jealous is usually when he feels he isn't getting attention. XD In that episode with Rudy, he brought out Charizard to hit the targets to impress Rudy, who paid no attention to him at all. In "A Fan with a Plan", Ash got jealous 'cause May/Max/Drew got recognized, and he didn't. I seem to believe Misty has given some hints, Ash just hasn't gotten it. He's too dense. (So cute. X3)
I think the only girl Ash ever (EVER.) fell for was Giselle. Not that I blame him or anything, I thought she was kinda cute. XD It was all obvious on that one. -nods- But like the person above me said, Ash is probably too much into Pok?mon to be concerned with his lovelife or whatsoever. (Awww, but the 5th movie was sweet, too.)
I prefer Advanceshipping for no particular reason. I just think it's cute. Again, I like one-sided stuff, so whether or not May has given off any hints, I don't think Ash notices it anyway.
I can tolerate Contestshipping.. I think Drew has a thing for May, I mean, the kid's been stalking her (Or desperately wanting to beat her). But he's already good enough, so why is he bothering? xx; In the Grand Festival, I'm pretty sure Caroline did accuse May and Drew as being lovers, but eh.. Don't fall for that act that Harley guy's pulling; he's only pretending to praise May, but what he really wants is to crush her. I've seen the Grand Festival episodes, and from what I can see, Drew seems to dislike this Harley guy. XD
I don't know whether or not that was a spoiler, but I'm sorry.. XD
[Aw, and at the end where Ash held an ice cream cone in front of May just after she watched Drew walk off was so cute/funny/sweet. XD]