What Event/Circumstance/Scenario would you like to see Ash shed tears for Misty?
Hmm, Ash strikes me as the jealous type. If he were to find out that Misty went off on her own journey with another guy and that she didn't even call Ash to even say goodbye, I think he'd be upset enough to cry. Not weep and sob for days, just shed a tear or two while he tries to come to terms with how he feels after such a turn of events. It's always Ash who goes on journeys, but how would he like it if Misty was gone, having all the fun with someone else?