First time posting on this site and shipping in general, but here goes
As I am from the first generation, I was a pokeshipper for a long time, that is until I saw Diamond and Pearl, and I instantly liked this pairing (high touch later sealed the deal). Dawn is my favorite of Ash's/Satoshi's companians and I love their relationship
Do u think that Ash will ever have the guts to ask Dawn out?
As much as I would love to see this happen, it probably never will unfortunately. As said by Hikatoshi26, they refuse to let Ash grow up. The best we will get is hints here and there, but that's about it :c