He seems half decent. I wondered before how she could have ended up with such bad apples, and the matchmaker thing makes sense there.
Also, what the hell is the tech level? I know there is magic and such, but it still feels weird that everything is vaguely medieval or preindustrial revolution-esque looking, yet at least one of the breakup/hero left you messages came via a prerecorded video of some kind.
As far as the previous heroes, were they actually happy? based on the clue from the princess that we got, it is very likely that their past engagements were at least partly political. Saintess, princess, and priestess right? All three are tied to major institutions. Major powers that can't afford to let someone like the hero off a leash once the calamity is over.